74. “I Was A Funny Fit in Both Worlds” (with Ana Gasteyer)

Summary

Podcast Summary: Sentimental Men – Episode 74: “I Was A Funny Fit in Both Worlds” with Anna Gasteyer

Release Date: July 7, 2025
Host: Broadway Podcast Network – Quincy Brown and Kevin Bianchi
Guest: Anna Gasteyer

---

1. Introduction to the Episode

Timestamp: [16:56]

In this episode of Sentimental Men, Quincy Brown and Kevin Bianchi welcome Anna Gasteyer, a seasoned Broadway performer known for her diverse roles and comedic talent. The hosts express their excitement about finally having Anna on the show, highlighting her extensive resume and connection to the theater community.

---

2. Anna Gasteyer’s Broadway Journey

Timestamp: [17:00] – [23:20]

Quincy: "An OG wish list item for us."

Kevin: "You are a dream guest for us because when we started this five years ago at this point, the original mission statement was to talk to all the Elphabas, what we call the golden age Elphabas."

Anna recounts her early career, emphasizing her time on Saturday Night Live (SNL) from 1996 to 2002 and her Broadway debut in the revival of The Rocky Horror Show as Usher in 2000. She details her subsequent roles, including May Coleman in Reefer Madness, Elphaba in Wicked (both Chicago and Broadway productions), Mrs. Peachum in The Threepenny Opera, and Kitty in The Royal Family (2015).

Anna: "Wicked came into my life at OG Wicked. It was such a unique and challenging experience."

---

3. Navigating Broadway Auditions and Imposter Syndrome

Timestamp: [25:05] – [43:34]

Anna delves into her audition experiences, particularly her journey to landing the role of Elphaba in Wicked. She shares candid anecdotes about her struggles with imposter syndrome and the daunting nature of Broadway auditions.

Anna: "Imposter syndrome is everything everywhere all the time. How do we teach people not to have that? Because it's such a useless waste of time."

She describes her initial auditions for Wicked post-9/11, highlighting her anxiety and the overwhelming process of learning the demanding vocal parts, especially the iconic "Defying Gravity."

Anna: "I couldn't do this show. Plus, I just found out I was pregnant with my daughter. So I was like, I can't do this."

Despite setbacks, Anna's perseverance led her to eventually secure the role, thanks in part to her dedication and the supportive environment at Wicked.

Kevin: "You doubted yourself, but you kept pushing forward."

---

4. Crafting the Character of Elphaba

Timestamp: [53:51] – [62:24]

The conversation shifts to Anna’s portrayal of Elphaba, exploring how she infused the character with her unique comedic flair while respecting the emotional depth required.

Anna: "I think that the role is written funny. I think she's a funny defense mechanism. And that was just a way in for me."

She discusses the balance between humor and drama in her performance, attributing much of her success to the collaborative direction of Joe Mantello, the director of Wicked.

Anna: "We rehearsed and then we did the show, and Mark Platt came in and saw it and left... there was not a lot of tinkering."

Anna reflects on how her ability to connect with her co-star, Stephanie Block, helped in creating a dynamic and engaging portrayal of Elphaba.

Anna: "Finding the connection through Elphaba's sense of humor was key."

---

5. Overcoming Challenges on Broadway

Timestamp: [62:24] – [75:23]

Anna shares the physical and emotional toll of performing Elphaba, particularly dealing with the perpetual stage fog and the demanding vocal ranges.

Anna: "The stage fog is a real challenge. It cuts your voice in half and gets in the way of everything."

She emphasizes the importance of maintaining vocal health and the rigorous demands of performing eight shows a week.

Anna: "It's physically hard and psychologically difficult. It's a role that demands everything from you."

Despite the challenges, Anna highlights the rewarding aspects of working on Broadway, such as the camaraderie and the fulfillment of performing live.

Anna: "Singing with other performers on Broadway is the happiest that I. Because it's... a bigger thing."

---

6. Future Projects and Creative Ventures

Timestamp: [78:34] – [81:59]

Towards the end of the episode, Anna discusses her upcoming projects and creative endeavors outside traditional Broadway roles. She mentions her collaboration with Rachel Dratch on Clusterfunk Christmas, a parody of Hallmark films being developed into a holiday musical.

Anna: "We have numbers from Hindenburg and a show called Death Race and a fake Lin Manuel show called Quantum."

Additionally, Anna introduces September L. Davis: Her Apology Tour, a show she recently debuted at Ars Nova, featuring original music from "fake musicals."

Anna: "We're developing it possibly to come here, which would be incredible."

---

7. Final Thoughts and Closing Remarks

Timestamp: [82:04] – [83:49]

The hosts, Quincy and Kevin, express their gratitude to Anna for sharing her stories and insights. Anna humorously declines the idea of returning as Madame Morrible, reaffirming her commitment to carving her unique path in theater.

Anna: "What would Bernadette do? She would never play Madame Morrible. Patty would never play Madame Morrible. Do not play Madame Morrible. Hell, no."

The episode concludes with a light-hearted exchange, underscoring Anna’s vibrant personality and passion for theater.

---

Notable Quotes with Timestamps

• Anna Gasteyer: "Imposter syndrome is everything everywhere all the time. How do we teach people not to have that?" [26:10]

• Anna Gasteyer: "The stage fog is a real challenge. It cuts your voice in half and gets in the way of everything." [53:35]

• Anna Gasteyer: "Finding the connection through Elphaba's sense of humor was key." [55:35]

• Anna Gasteyer: "What would Bernadette do? She would never play Madame Morrible. Patty would never play Madame Morrible. Do not play Madame Morrible. Hell, no." [76:54]

---

Conclusion

Episode 74 of Sentimental Men offers an intimate and comprehensive look into Anna Gasteyer’s illustrious career in musical theater. From her early days on SNL to her transformative role as Elphaba in Wicked, Anna shares personal anecdotes, challenges, and triumphs that illuminate her dedication and passion for the craft. The episode not only celebrates her achievements but also provides valuable insights for aspiring performers navigating the demanding world of Broadway.

---

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• Twitter/X: @entmenpod
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Transcript

[Anna Gasteyer]

Hi, y'. All. This is Kristin Chenoweth. Hi, I'm Gloria Stefan. This is Sara Bareilles. Hi, I'm Patti LuPone. This is Lin Manuel Miranda.

[Quincy]

You're listening to the Broadway Podcast Network at Capella University.

[Anna Gasteyer]

Learning online doesn't mean learning alone. You'll get support from people who care about your success, like your enrollment counselor, who gets to know you and the goals you'd like to achieve. You'll also get a designated academic coach who's with you throughout your entire program. Plus, career coaches are available to help you navigate your professional goals. A different future is closer than you think with Capella University. Learn more at Capella. Edu. Starting a business can seem like a daunting task unless you have a partner like Shopify. They have the tools you need to start and grow your business. From designing a website to marketing, to selling and beyond, Shopify can help with everything you need. There's a reason millions of companies like Mattel Heinz and Allbirds continue to trust and use them. With Shopify on your side, turn your big business idea into sign up for your $1 per month [e-mail] specialoffer. Ask yourself, what would Bernadette do? What would Bernadette do?

[Quincy]

What would Bernadette do?

[Anna Gasteyer]

She would never play Madame Morrible. Patty would never play Madame Morrible. Do not play Madame Morrible. Hell, no.

[Kevin]

Oh, my God. I'm Quincy.

[Quincy]

And I'm Kevin.

[Kevin]

And this is Sentimental Men.

[Quincy]

We're here to talk and maybe scream about our favorite women in musical theater.

[Kevin]

She is kind. She is smart. She's the. That I am not. Tell me where that's from.

[Quincy]

I couldn't if I tried.

[Kevin]

From the moment that she says, it's Betty, hi, you will never.

[Quincy]

If you let her now I'm in. There's gonna be people listening to this, going, like, screaming the lyrics at you.

[Kevin]

I really feel like I need to see Betty Boo before it closes.

[Quincy]

I know. Me too. Do you want to go?

[Kevin]

Yeah. But when does it close?

[Quincy]

Or did it or. No, they. They're one of the later closings.

[Kevin]

It closed on July 13th.

[Quincy]

Okay, we have 10.

[Kevin]

I'm out of town this weekend, but then let's enter the lottery every day. Okay. Because I do think I'll love it. I just never got around to going just to it.

[Quincy]

Yeah, you've been busy. It's been a busy couple of months.

[Kevin]

And now it is. Betty Boop is a part of the onslaught of closings that we received post Tony's.

[Quincy]

It felt like a lot this year. I mean, there's always several. But it felt like a lot closed very quickly this year.

[Kevin]

Yes, but. And then it also felt like a lot were hanging on longer than they should have been post Tony's. I'm very sad about Smash. Very sad about Dead Outlaw. Very sad about real. Very sad about them all, I guess.

[Quincy]

Actually, I am trying to reframe my thinking because I always get so sad, like, in July when all of the shows start closing. And I'm really trying to reframe my thinking as, like, a season being its own thing and, like, things close at the end of the season. Like, I'm trying to think of it like the end of a school year and then a special treat to go on to the next season.

[Kevin]

Well, yeah, I mean, technically, like, not every show is supposed to run forever.

[Quincy]

Yeah.

[Kevin]

And I do think there's been a little bit of a narrative, like Broadway is in such trouble because all these shows keep closing. I'm not sure that's. Well, I think Broadway is in trouble from an artistic standpoint. From a commercial capitalist standpoint. I think Broadway is just fine. And I think finding the middle ground is going to be the struggle of these next five, 10 years.

[Quincy]

Yeah.

[Kevin]

Also, though, I feel like there's not a lot of new musicals announced for next season.

[Quincy]

No. It's revival heavy, huh? It's a lot of not even revivals, just, like, remountings.

[Kevin]

Because what are the. It's Queen of Versailles and Wanted are the two that we know about.

[Quincy]

Yes, there might be one or two more, but. Yeah.

[Kevin]

And Wanted doesn't have a theater announced yet. It's just odd to me that there has to be more coming.

[Quincy]

I surely would hope.

[Kevin]

Did you buy Chess tickets?

[Quincy]

No, not yet. I'm hoping that somebody I know will offer me some. I am really excited for Chess. Chess is one of my favorite cult y musicals.

[Kevin]

Are Mamma Mia. And Beetlejuice going to be considered revivals or are they just going to kind of be special event situations?

[Quincy]

I think probably. Well, I guess it depends on how long they're running because the Wiz was.

[Kevin]

A tour, but that was considered a revival.

[Quincy]

The contracts on these things are always so weird. It depends if the tour and the Broadway sit down are two different contracts.

[Kevin]

Mm.

[Quincy]

I think. I don't know.

[Kevin]

It is so cool to see the Mamma Mia. Marquee up at the theater like that. Just feels like such an iconic New York City Times Square image. And the fact that it's live in person in 2025 is so crazy.

[Quincy]

Yes, Yes.

[Kevin]

I really want. I want to go to Margaritaville and then see Mamma Mia one day.

[Quincy]

It feels like that was the sole purpose of creating Margaritaville. It was just like someday Mamma Mia. Will come back. Margaritaville, the musical was. Was not the. The ticket. But if we can get Mamma Mia to come back, they. I mean, that's the cross promotion opportunity of the decade.

[Kevin]

I'm very excited for that.

[Quincy]

We're having a Mamma Mia Margaritaville girl summer. This summer.

[Kevin]

Mama Vit.

[Quincy]

Mama Vitaville.

[Kevin]

Margamita. Ville. Margamill.

[Quincy]

Margamia.

[Kevin]

Margamia.

[Quincy]

Here we go again.

[Kevin]

Oh, Kitchen. Margamia. No, I'm excited. I'm excited for this next season. I feel like fun stuff is happening. Sad about all the closings, but thank you. Next, I guess.

[Quincy]

Thank you.

[Anna Gasteyer]

Next.

[Quincy]

I'm excited for rack time as well.

[Kevin]

Me too.

[Quincy]

And also, is it confirmed, the Rocky Horror or is it.

[Kevin]

I don't know what you're talking about.

[Quincy]

Oh, okay. I've heard a lot of rumors about Rocky Horror going into Studio 54. I will not ask you to comment on these rumors. I will just say that I have been hearing about a Studio 54 revival of Rocky Horror since I started at Roundabout in 2020.

[Kevin]

I was gonna say, when we were at Roundabout, I feel like they were talking about reviving Rocky Horror.

[Quincy]

Yes. I mean, I don't know how, like how much longevity a Rocky Horror revival has.

[Kevin]

You think if it's done right and with a cool angle, it could run.

[Quincy]

I think it could run at least through the end of the calendar year.

[Kevin]

You couldn't turn it into like a Star Cassie thing that.

[Quincy]

Well, I think that would be the. The opportunity would be if you could get like B level pop girlies to do six week stints, especially as, like, if you can get like hot young things to be Brad and Janet. Like, those are the easiest roles to stunt cast in. And I feel like just little shot bit. You know what? I did watch since the last time that we spoke. No, but I did listen to it. I was trying to move us into our. Because of the Spider Woman.

[Kevin]

I gave such an impassioned plea for you to watch Next to Normal.

[Quincy]

I have not watched it yet. I have listened to it and it has made me excited. Okay. I'll give you a little opinion about the cast recording though.

[Kevin]

Okay.

[Anna Gasteyer]

Is.

[Quincy]

Well, number one, obviously, Casey Levy is astounding and is like, it's a tragedy.

[Kevin]

That that's not coming to Broadway.

[Quincy]

I know. And is like singing this role in a way that sounds so Easy. It's just like, you could tell me this role was written on her. It fits her so well, which is really incredible.

[Kevin]

Probably a little higher if it was written on her.

[Anna Gasteyer]

Yeah.

[Quincy]

But it's so, like, nice and sustainable. It's like, it. It sounds like she can do it eight times a week, no problem. I love Jack Wolfe as Gabe. I think he's like. I think he really is, like, nailing the sound of the show. Obviously, I haven't watched it, so I don't know about his, like, performance, but I love his vocal performance.

[Kevin]

I'm Alive is great.

[Quincy]

I'm Alive is great. He, like, nails the American ness of the sound. I feel like. Like, he sounds really like American musical theater, which in that particular show, I feel like is important to translate. I'll watch it soon. Now that Connor's back, we'll watch it.

[Kevin]

I was in Spain for the last two weeks. Yeah. Desperately. I hit my head on a tree in Spain, which is why I'm wearing a hat if you're watching on video. But I was desperately trying to get Matt to fly with me to London to see Rachel Ziegler in Evita because I feel like those videos over my feed.

[Quincy]

Correct. Same.

[Kevin]

No such luck with Matt. However, I am very, very excited to either see it there or here, whenever that does end up working out for me.

[Quincy]

Yeah, yeah.

[Kevin]

She sounds insane.

[Quincy]

She sounds insane. Another one where it's like, you're singing this like it's easy. Can I ask a question? And this is not a question from a place of judgment. Oh, do you know, like, what the Che is covered in at the end of the show? Like, I respect the choice. I'm not judging the choice. But like, with Sunset Boulevard, I'm like, oh, it's blood. Like, it's. It's blood. Because he dies and this looks like he, like a birthday cake situation.

[Kevin]

I do not know. I do not care.

[Quincy]

I'm not complaining.

[Kevin]

I am excited to find out. I also am, like, over the conversation about, is Jamie Lloyd a one trick pony? Is he just ripping the sunset thing? Who cares? It's all fun and exciting and new. Every Andrew Lloyd Webber show sounds like an Andrew Lloyd Webber show. Every Sondheim show sounds like a Sondheim show. There are other directors with calling cards as well. Look at a Casey Nicholaw show. Look at a Jerry Mitchell show.

[Anna Gasteyer]

Yes.

[Quincy]

Instruments on stage.

[Kevin]

Look at an Alex Timber show. Like, it's all. Everyone has their thing.

[Quincy]

People have trademarks.

[Kevin]

And this is fun and exciting and, like, giving a new life to Alw shows, which I'm very grateful for. It sounds good. It looks cool. The choreo seems fun. There seems to be more costumes in this one than in Sunset. Maybe just by a small margin, but I'm just. I want to see what's happening in there.

[Quincy]

Me, too. I remember thinking while I was watching Sunset, I was like, every drama teacher or, like, head of a theater program should be, like, watching this, learning how to, like, do a show with no set. Like, he really is. Point out whatever similarities you want. But he really is a very, like, innovative and, like, inventive director. So I'm sure there's. I'm sure it's fine. I'm sure I'll agree with the reasoning for the COVID I just am curious what it is.

[Kevin]

Yes.

[Quincy]

What is it?

[Kevin]

Because it's, like, blue and white.

[Quincy]

It's in several colors, which, like, blue and white is the Argentine. Argentine flag.

[Kevin]

Maybe it's like a political. Maybe it is supposed to be blood. He's covered in the political blood.

[Quincy]

Maybe it's paint.

[Kevin]

We'll find out.

[Quincy]

We'll find out.

[Kevin]

People are saying about Evita that if you don't know Evita, seeing this for your first time is going to be real tough to follow what's happening. I kind of feel Sunset is. That production of Sunset is a very similar situation where, like, I had friends come out and be like, why was she talking about a monkey in the beginning? And it's like, oh, yeah, you're not seeing the, like, dead monkey. So you. If you're not really paying attention to what's being said and using your brain, a lot can fly over your head.

[Quincy]

Yeah, I feel like that the monkey was like, the only moment where I was like, I could have used a prop or a blanket on the ground or something.

[Kevin]

I could imagine all the Hollywood studio stuff being like, what's going on? Who are these people? Where are we right now?

[Quincy]

See, I feel like people who are saying that. I actually feel like the lack of all the other stuff made it easier to follow.

[Kevin]

Interesting.

[Quincy]

There's no. Because there's less distraction. So it's like, if you're actually, like. And especially a show like that, it's so sung through practically that it's like, if you're listening to the score, I found it easy to follow along. But I guess maybe I. I know the show already, so maybe.

[Kevin]

But that's also. I'm a little curious why people are saying that about Evita. Because I feel like Evita, the score really lays it out for, like, you were Just following the story forward.

[Anna Gasteyer]

Yeah.

[Kevin]

It's telling you what's going on. And there's a narrator kind of taking you through it.

[Quincy]

There's literally a narrator. There is someone direct to audience saying, and now she's moving to Buenos Aires.

[Kevin]

And now she's money kept rolling.

[Quincy]

I can't wait to hear Rachel Ziegler sing Rainbow High.

[Kevin]

He sounds great too.

[Quincy]

He does, he does.

[Kevin]

It's like so sexy and sultry. There's an audio of Rainbow High out. There's an audio of everything out there.

[Quincy]

I know I haven't listened to it yet, but I will.

[Kevin]

So good. Oh, my God.

[Quincy]

Rachel Ziegler, we love you. We love you. We've loved you since west side Story. No, that's a lie. We've loved you since YouTube.

[Kevin]

Since YouTube. Shrek at your New Jersey high school.

[Quincy]

I know. She's a Jersey girl like me. Wait, Quincy, one more thing before we talk to our guest today. Have you seen the trailer for Kiss of the Spider Woman starring Jennifer Lopez? That is going to be a very sentimental men coded event film experience.

[Kevin]

When does it come out?

[Quincy]

Sometime in the fall. I forget the exact date. Hold on.

[Kevin]

This fall? It's coming out around Wicked time.

[Quincy]

In a couple months. Yeah.

[Kevin]

Interesting.

[Quincy]

Bold.

[Kevin]

Yeah.

[Quincy]

Probably before Wicked, it's giving like September to me.

[Kevin]

I was. I thought it was going to be starkly after Wicked had wrapped it up October 20th.

[Quincy]

So like, whoa, six weeks before Wicked.

[Kevin]

Interesting.

[Quincy]

So they're trying to sneak in right before people start paying attention to. To Wicked. Wicked.

[Kevin]

Fascinating. Okay. I mean, the trailer does look phenomenal.

[Quincy]

It looks fabulous and it's really giving. I mean, I think it like says this in the, in like the voiceover, but it really is giving, like role she was born to play because it's like she looks fabulous. She obviously they can like really make her dance in a role like this, which is great. I think that's like a strength of hers that she doesn't always get to use on film.

[Anna Gasteyer]

And.

[Quincy]

And I think something that's so important to that role is just like the je ne sais quoi, like the it factor. And she just has that.

[Kevin]

Which she does have.

[Quincy]

Yeah. And so I really. It just like it's perfect casting for her to be this like, glamorous movie star that like this gay prisoner is obsessed with. It's perfect.

[Kevin]

And it feels like the perfect thing for her to be doing in her career right now.

[Quincy]

It's so good. Like, of all the musicals that she's kind of been like, attached to or.

[Kevin]

Happened to that Bye Bye Birdie.

[Quincy]

It's gone, it's done. It's. They have officially pulled the plug. But even like this, I think is a better fit than that. Or like when, like, I remember when, like the in the Heights movie got greenlit, they were like, well, JLo's gonna be in it.

[Kevin]

And I'm like, oh, interesting. Yeah. As who?

[Quincy]

As who?

[Kevin]

I'm excited for it. Did not realize it was coming out so close to Wicked.

[Quincy]

I know. We'll be blessed. We'll be blessed.

[Kevin]

Oh, Kevin. I'm going to see Cynthia Erivo and Jesus Christ Superstar at the Hollywood bowl on August 3rd.

[Quincy]

Oh, my Go. I'm so jealous. That's amazing.

[Kevin]

I'm very excited.

[Quincy]

Anyway, who's. Who's Pontius Pilot in that? Who's the other headliner?

[Kevin]

I'm not sure if it's Adam Lambert, isn't it?

[Quincy]

Oh, Judas as Judas. That's right. That's right. Cynthia and Adam.

[Kevin]

No, I'm super excited for that.

[Quincy]

I can't wait.

[Kevin]

I have a wedding in New Jersey on the 2nd, and then I fly to LA on the 3rd and see the show on the 3rd, and then I fly to Hawaii on the 4th.

[Quincy]

For a vacation well deserved. Speaking of the Hollywood bowl, today's guest has performed there.

[Kevin]

What a segue, Quincy.

[Quincy]

Today we're talking to Anna Gasteyer.

[Kevin]

Long time coming.

[Quincy]

An OG wish list item for us.

[Kevin]

Well, let's talk about how this actually happened.

[Quincy]

Yeah, let's talk about it.

[Kevin]

So when we first started the podcast, she was like a dream guest. And then we in our, like, early, early TikTok days in like 2021, posted a video of her doing Defying Gravity and then commented on that video, our own video, saying at Anna Gastar, we would love to have you on the podcast. And then forgot, obviously forgot about that. And then I got to work on Once Upon a Mattress, but I didn't want to, like, also ask her to be on the podcast as I was working on the show because it felt weird. And then randomly a couple weeks ago, she. She responded four years ago saying, yes, hi, I would love to. And then her social person reached out and we got it together. So four years later, yeah, she saw our comment and replied, which just goes to show.

[Quincy]

Shoot your shot, guys. Send the dm, make the comment.

[Kevin]

It was really funny.

[Quincy]

No, it is really funny. It's like any, at any point that we could have stopped making the podcast. I'm glad we didn't, because this long game really is insane.

[Kevin]

Okay, let's go through her mile long resume.

[Quincy]

All right, so, yeah, really a mile long because she works. So Anna Gasteyer was, of course, a cast member on SNL from 1996 to 2002.

[Kevin]

Wow.

[Quincy]

She's got, like, plenty of iconic imperson, impersonations, sketches. Celine Dion obviously is like, one of the more famous ones. I feel like she sang a lot on snl, but she never, in a way that was supposed to be, like, impressive. Like, it was always part of the joke or just like part of the impersonation. And it's like if you were like, really listening, you're like, oh, wait, but she's like singing like Celine Dion. Like, she's got the voice. So that was kind of her. Well, she'll get into it how she worked that into a musical career. So in 2000, mid SNL, between two seasons, she made her Broadway debut in the last revival of the Rocky Horror show as Usher at Columbia opposite Daphne Rubin Vega. In 2005, she was May Coleman in the movie musical of Reefer Madness, one of my favorites. She's so good in it. Also in 2005, she made her Wicked debut as Elphaba in the Chicago company of Wicked in 2006, Mrs. Peachum in the Threepenny Opera in 2006, also Elphaba in Wicked on the Broadway in 2009, she's back on Broadway as Kitty in the royal family in 2015. A personal favorite of mine, Mimi Schwinn in A New Brain at City Center.

[Kevin]

Gotta have heart and music. Oh, I'm just remembering her falsetto story.

[Quincy]

Yeah.

[Kevin]

Okay.

[Quincy]

In 2016 and 2017, she did some of those live musicals. She was Principal Mickey on Grease and she was Mrs. Schwartz on a Christmas Story.

[Kevin]

I think Grease is my favorite live.

[Quincy]

It's one of the best.

[Kevin]

Or maybe Hairspray.

[Quincy]

I think Greece was better.

[Kevin]

Really?

[Quincy]

Because I think I had a dream.

[Kevin]

About Maddie Balio last night.

[Quincy]

Do you want to talk about that?

[Anna Gasteyer]

I just remember.

[Kevin]

But she wasn't Maddie Balio from the Hairspray Live. She was just Maddie. She was just a character in my dream.

[Quincy]

Maddie from Accounting.

[Kevin]

Continue.

[Quincy]

In 2019. This is very important to me because it's my favorite show on television. In 2019, she competed on the Masked Singer as the Christmas Tree. She made it pretty far too, if I remember. And she's like the perfect kind of person for that show because it's like hidden vocal talent. But when she takes the mask off, you're like, oh, I. I know who this is. Sometimes they take the mask off. I'm like, Who?

[Kevin]

Yeah. You actively watch the Masked Singer.

[Quincy]

I absorb the Masked Singer like I absorb no other show on television. They pump out, like, three seasons a year, and I am in it. I keep notes of who I think it is interesting. It's very catered to the way, I think, because you get little clues and then it's just like, voice recognition. I would be an excellent judge on that show.

[Kevin]

You know what show I'm hooked on this year? For the first time ever?

[Quincy]

I can guess.

[Kevin]

Love Island.

[Quincy]

Yeah, that feels right.

[Kevin]

It's so good. I've never watched it before. There's five episodes a week, and they're all an hour long. And it is such a commitment, but it's such fantastic television.

[Quincy]

Yeah, I know. I do feel out of the conversation because I didn't start it on time. Like, I didn't start it with everyone. And now I just feel like it's impossible.

[Kevin]

I had to. I took a week off when I was in Spain, and then I realized I was falling so behind, so I had to, like, buy a VPN and, like, try and figure out how to download it in Spain.

[Quincy]

It's.

[Kevin]

Yeah, but it's so good. Anyways, continue.

[Quincy]

Anyways, in 2024, Anna was back on Broadway as Queen Agravaine in Once Upon a Mattress. Her other theater credits include Aunt Deb in the Kimberly Akimbo play. Back in the Day, she was Miss Hannigan in Annie at the Hollywood. She did Funny Girl at Pittsburgh C Lo, she did Funny Girl and Hair Actors Fund benefit concerts. We love those on TV and film. Of course, we know her from things like Mean Girls, American Auto, suburgatory. She has two studio albums, 2014's I'm Hip, which is a collection of jazz standards. And then in 2019, her Christmas album, Sugar and Booze, which is so good. I love Christmas music, and I feel like people don't really talk about her album.

[Anna Gasteyer]

It's really good.

[Kevin]

Is it as good as Idina's Holiday Wishes?

[Quincy]

It's as good. And it's a lot of original music, too. Like, it's a lot of, like, comedy songs.

[Kevin]

All right, I'll add it to the rotation this year.

[Quincy]

Add it to your Christmas in July playlists.

[Kevin]

I don't think I've ever laughed as hard in an interview.

[Quincy]

Yes. I really liked doing this interview.

[Kevin]

I'm almost concerned to start the edit of it, because I feel like it's going to meander quite a bit.

[Anna Gasteyer]

Yeah.

[Kevin]

So just. Just ride with us, guys.

[Quincy]

Yeah, yeah. In this interview, I also feel like she showed up Ready to gag us. She was like.

[Kevin]

I don't even think she was like ready to gag us. I think she was just like stream of conscious flowing and giving us really great stories. Nothing like crazy or bad, but just like really interesting stories.

[Quincy]

I'm excited. You guys are really going to like this interview.

[Kevin]

Yeah, really some really fun stories that I feel like probably haven't been shared before or shared in as much detail. She even made a comment about how she would like typically abridge these stories. But we seem like the type to people who would.

[Quincy]

Yeah, yeah. I just think her, her journey is really interesting.

[Kevin]

Yeah, let's get into it.

[Quincy]

Let's get into it. Enjoy everybody.

[Kevin]

You are a dream guest for us because when we started this five years ago at this point, the original mission statement was to talk to all of the Elphabas, what we call the golden age Elphabas.

[Anna Gasteyer]

Oh nice. Retirement home Elphabas.

[Kevin]

No, the initial crop of women who made the role what it is. And we a while back talked to Julia Murney. You are a very important piece of a story that she kind of started for us.

[Anna Gasteyer]

Oh really?

[Kevin]

Yeah, she mentioned that. Actually, you know what, let me bring that up later. Let's start with how did Wicked come into your life as a person?

[Anna Gasteyer]

Wicked came into my life at OG Wicked. So total boring. Since this is a Wicked story, I would ordinarily abbreviate the story. Republicans, please don't.

[Kevin]

But spare no details.

[Anna Gasteyer]

2001, right after 911 I was called in I think for the. It was, it ended up being the final. I was called in. I don't even remember the details, but I do remember that the final callback was after 911 because no one was like going anywhere. You know what I mean? Like the whole city was shut down. And it was, I believe, Idina, Julia Murney and me for the final callback. And I was not available. I was on Saturday Night Live so. And I was. And I just found out I was pregnant with my daughter. So I was like, I can't do this show. Plus like, so I literally went to like Stephen O. Remus's apartment because I remember it was like very like, you know, like, you know, Stephen Schwartz is only going to be in town for three hours. Stephen Schwartz is on the way to the airport and is only going to be there for 15 minutes. And I was like, all this, like there was all these changes in that, like.

[Kevin]

And was there like a word on the street on what this was at that time or kind of just a new project?

[Anna Gasteyer]

I knew very Little about it. I knew very little about it at that point. Again, I was on Saturday Night Live. Like, I was in a different. I had done, like, a few. I had done Rocky Horror that summer, and so I was kind of in. Like, I had, like, been inducted into the Broadway community, and I had done, like, a bunch of readings, mostly through, like, through Mark Shaiman, who had worked at snl. So I'd, like, done the first reading of Hairspray, like, back in the day. Like, Penny's mom was, like, a role in, like, one of the early, early readings. And then y. So it kind of, like, I'd done, like, a few things like that, but I wasn't, like.

[Kevin]

Dialed in, pounding the Broadway pavement.

[Anna Gasteyer]

Not. Not. Not really. I mean, I was admiring of it and kind of, like, you know, secretly longing. But I. I'm a. I cannot learn choreography at all. Like, I have, like, a disability. Like, I can dance, but I can't. I mean, dance. I can move. Like, I can sort of make it. Fake it. But I. Early on, I was like, oh, I can't. I can't do, like, big chorus calls. And. Because I will be cut in the first round. Like, the only things I'd ever done was sing or comedy. So when, you know, like, Rocky Horror, like, those things came in through the. Through the, you know, Saturday Night Live door. So. And I started seeing. Like, I auditioned. God, why am I telling you all this? I'm. I. Yeah, I was, like, flirting with it. Like, I'd auditioned for, like, at the Public, and I'd auditioned for, like, Summer, you know, for. On. When they did that revival on the Town. And I did, like, I'd shown up for some stuff and gotten called back, but I really didn't know what I was doing. And I was really, really intimidated, and I still am, by, like, the Broadway kids with their books and their. You know, like. Like, to this day, like, I had an audition, like, I don't know, a couple years ago. They're like, bring your book. And I was like, I don't have a book. I still don't have a book. And sing from, like, a show that I have been in, but, like, I don't have a book, you know, and, you know, whatever. Like, God forbid, like, you get thrown any. Like, the. Like, the words that will, like, freeze my intestines are like. And then they would love to, like, work with you and the choreographer. And I'll be like, yeah, it's like, just don't waste my. In fact, I wish I had. I would have spared Myself many humiliating experiences. If I had just listened to my gut and been like, I don't do that. But, yeah. So I guess at that point I was like, really? So that was the very og. So I went to Stephen O. Remis's house apartment, which was a disaster. It was like a postage stamp in Hell's Kitchen. And I remember it was like, you know those, like, shower curtains that, like, are kind of semi permanent, like, vinyl, and it was broken. Like, it was at, like, an angle. I was like, what is this? What is happening? And. And he. And I'll. All I remember is. And they played the music. He played the firing gravity. And I was like, oh, that is way too high. I can't. Like. I mean, it sounds so negative, but I remember just being like, I can't sing this. It was so high. It was so high. I was like, that's really high. What's that note? And I didn't even know. Like, I didn't know I hadn't been taking voice. I. I was a voice major in college. I was a music school dropout. I found comedy. I did comedy, and singing was like a party trick at that point in my life. And then I did Rocky Horror. And then I sort of, like, started to reverse. I did some ensemble stuff and, you know, like, in these readings or whatever and.

[Quincy]

Have you done Funny Girl at Pittsburgh Cielo?

[Anna Gasteyer]

I hadn't done anything at this point. This. The point that I'm telling you. I was like. I was still on Saturday night. I was like, I think I like Broadway, but I'm not. I'm not sure. And I was obviously, as I've told you by the 75 embarrassing stories that I shouldn't have shared on public. In the Public. Like, I wasn't. I had a lot of anxiety before I had, like, about preparation and about how to do it. And was there a club, like, a Weight to be. And I do think that Broadway kids are. They're more disciplined than other. I don't know. I just had a thing in my head, like, if you didn't go to dance class every day. And this is why I. You know, because to back it up even further, when I was, like, a opera voice major, like, Northwestern didn't even have a music theater, like, program, then you were either a theater major who did musicals, but that was, like, your side hustle, you know?

[Kevin]

Right.

[Anna Gasteyer]

And it's the Midwest, so it's like, I did one. One musical while I was there. There's this big review there called the WAMU Show. I did that my freshman year, like, I got in, but everybody was, like, kind of mean to me. And they. Because they. They told me. They're like, we thought you were, like, a lesbian. English. English major. Someone told me that. Can you believe that? And I was probably like. I was like, it was exactly, by the way, what I do. It was like, comedy sketches and. And singing. Right. So. But anyway, I. All these people, like, this girl dropped out because she got into Disney Tokyo. Like, all those Midwest kids, like, they were like Six Flags every summer. And, like, they'd all been taking tap class since they were, like, you know, in the womb. Like, so it was just a different, like. And I. I just didn't feel equipped when I got, like, I've said 5,000 times in New York, I was like, I don't even know where to begin with that. Like, I am just gonna excuse myself from this situation. So then when casting. When people would call me in, I was kind of like, I'm. I'm an amateur. I'm a. You know, it's like, imposter syndrome is everything everywhere all the time. Right? How do we teach people not to have that? Because it's such a useless waste of time.

[Kevin]

Yeah.

[Anna Gasteyer]

So I was convinced I was an imposter. In summary. And Stephen o. Remus's high Ds in his disastrous apartment absolutely reassured me of my imposter status. So that went away. And then I did my final season on snl. And during my final season of snl, I was just kind of like, more and more. Like, I think. I think I want to really double down and I want to drill down. And part of this imposter syndrome led to. I was like, I need to get back into. I hadn't taken a voice lesson since I was, you know, 19, so I was like, I need to get back into this. And I was very close friends with Seth Rudet's by complete coincidence, because Seth wrote for the Rosie o' DONNELL show, and we met at the NBC gym on the eighth floor on the treadmills, when he made fun of my outfit because they gave you, like, a signed. They gave you, like, it was so great. It was a corporate gym. So they give you, like, the. They gave you clothes, and they were like, we'll wash them, and you just keep your gym clothes at the gym. Right. But they were kind of like intramural ladies volleyball shorts. Do you know what I mean? Like, they weren't cool. They were just like a weird, bad, like, intramural, like, corporate brand. Yeah. He was like, way to wear the assignment. Yeah, literally, like, the peacock. And they were just dorky and. But I was like, great. Like, I don't care. Like, I'm just on the treadmill. And he was like, way to wear the assigned shorts. Like, he totally busted me for the uniform. And we became friends right away. I was like, oh, this guy's like, one of us. Like, one of me, I should say, because I'm. I'm a weirdo. And so Seth, like, we're both, like. I was, like, a music major, but I didn't know anybody in the comedy world who, like, as much as I was just spoken to all this imposter. It was the same in Mute. Like, in comedy where, like, I was a little bit of a wonk. Like, I was a little bit of a. Like, you know, could read music. And I played violin for 16 years. So I had, like, a weird. Both. Both worlds have a funny fit for me. Anyway, so I. Seth was like, you. Every time I'd say, he was like, you belted, you know, a G when you were doing, you know, he was always, like, telling me what I'd done and, you know, and ca. Character, like, so I wasn't. Because all my characters sing on snl. So I wasn't, like, thinking about it musically. I was thinking about it creatively and artistically and coming to it from the organic, happy place of telling a story, of being the character. And so I can't remember what order it was in, but Seth did. I think he did the. He did an All Star Funny Girl benefit for Actors Fund with, like, a gazillion. So everybody was in it. I mean, divas, Adina and. And, yeah, all the divas. Like, literally everyone.

[Quincy]

Sutton, Kristen, all of them.

[Anna Gasteyer]

Right, exactly. Sutton, Kristen, exactly. That's where I met all those girls.

[Quincy]

And what song did you do in that?

[Anna Gasteyer]

I did the. Isn't this the height of nonchalant. Yeah, love was great. And we. And I was just off snl and I. And so then I did in sort of sequence. I don't remember the order of things, but I did a play at MTC right out. That's the first thing I did when I left the show because I'd done a reading and they offered me the role, and I ended up. It was the original play of Kimberly Akimbo.

[Quincy]

Yeah.

[Anna Gasteyer]

So I played Aunt Deborah. So I just. I. That was my first, like, job when I left snl.

[Kevin]

And that was a deliberate choice to return to go to theater after snl as opposed to chasing some sort of comedy screen Career super deliberate.

[Anna Gasteyer]

Like, like, I took the job. So I couldn't return to SNL because I loved the reading and I didn't, you know, it's. It again. I fall between worlds. And it was just a little bit not great for women in TV yet. Like, at least women who didn't fit a certain mold. Like, I mean, you might get like somebody's wife or something. You know, that. That would be like the. The big comedian would get the. Get the overall deal at NBC and develop the haha funny family show and then you would maybe be called into audition for the wife. But that happened a lot for me. So I don't know. I was like, yeah, I don't. I don't want to do that. And I guess I could have developed something, but I just didn't. I don't know. I didn't. But anyway, so. And I was really. And in one week, I remember this so clearly, is. It must have been like October of that year. My manager is like, there's no work for women in film. So I don't, you know, let. We should probably pursue, like, I don't know what you want. And then I went in one week, I saw A Wonderful Town with Donna Murphy and I saw Wicked. And in the same weekend, I was like, I'm gonna stay in New York. Like, this is a much better path for me and more fun. It was just what I wanted to do. I mean, it was a super road less traveled at that time. Like, nobody from SNL did that crossover. That was a strange choice, right?

[Kevin]

Yeah.

[Anna Gasteyer]

Anyway, that's what I did. So I doubled down. I did Kimberly Akimbo. I must have done a bunch of readings. I have no memory. You know, I auditioned for everything under the sun and didn't get it. I'm trying to remember what. I mean, it was like the Little Shop revival was at that point.

[Kevin]

Oh, wow.

[Anna Gasteyer]

There were a bunch of things. A bunch, a bunch, a bunch of things. And I didn't. I still to this day, I'm a terrible, terrible musical theater auditioner. I really am. It's astonishing. My, my, my. I mean, famously. Let me tell you the falsetto story one day, but.

[Kevin]

Ooh, please.

[Anna Gasteyer]

Yeah, the. It's really a bummer because it's so much work and the level of preparation is so above and beyond, by the way. Like, I love that, like, actors are like, you know, in SAG or furious about going on tape for things. And I'm like, right, try musical theater auditioning. It's like 32 pages of sides and 300 pages of music that you have to learn.

[Quincy]

And maybe you'll do five pages when you get there.

[Anna Gasteyer]

Maybe you'll do five pages. And it's like the least friendly room in all of auditioning. It's like four scary people behind a table very far away. And that none of that has changed do you know, like, and it's just, it's just an unbelievable level of preparation required. It's like a week's, you know, 40 hours of rehearsal for something you, you know, it's hard to get yourself in the brain of like I deserve this and this could go my way, you know, from that like auditioning psych level. So time passed. I can't remember what year it is now. This is so unbelievably boring. And I'm so sorry. I'm bored. I'm actually bored by myself and annoyed by myself.

[Kevin]

So you've already seen Wicked on Broadway?

[Anna Gasteyer]

I've seen Wicked on Broadway. I double down. I do. I say yes to everything. Every workshop, every out of town show. I do Pittsburgh clo, Funny Girl. I do. Like I just. Anything I could do, I did it. At this point I started studying again, vocalizing every day. Like just kind of like feeling it out, going and seeing stuff, staying open and interested. And then they call, they, they called me and my agents were like, you obviously want to do this, you're insane. And I auditioned for Wicked. It must. So Idina's leaving. This is fast forward to Adina's leaving and I think so they bring in a very small group. I must. I can't remember the audition process, but I. The callback was a very small group. I must have done the. I don't remember. But anyway, I knew it was me, Shoshanna, Eden, maybe Stephanie.

[Kevin]

What was the Daphne Rubin Vega room? Was this that initial workshop? Because Julia had a story of a room that was you, Shoshana. Daphne. And she recalled it as being for OG Elphaba and Adina.

[Quincy]

I feel like Quincy, you're think that, that you're thinking of is pre workshop.

[Anna Gasteyer]

That may have been the pre workshop room that she's talking about. Yeah, that's the one that I'm remembering. The callback was in Stephen O. Remus's. Sorry, I should have clarified by the way, when he what it was after 911 he tape recorded me. We didn't even have have phone recorders then.

[Kevin]

And I think he played that tape.

[Anna Gasteyer]

Like I didn't end up going God, burn it by the way. Because as noted, I was like, I can't sing a D. So I think he probably was like, she can't do this. I don't know. But I never went back in person for that final callback. I went in person right after a 911 for the first audition. And then the second audition was to learn Defying Gravity, and it was again after 9 11. My head was like, I was going back to SNL. I was. And like, I was like, oh, I can't do this job. I can't go to San Francisco. So I'm not, you know. So I went to Stephen O. Remus's, sang into a tape recorder poorly, and then judged his apartment and left. So. Which I've said to him before. So I. And by the way, he now has a very beautiful apartment.

[Kevin]

Sure does.

[Anna Gasteyer]

Nicely appointed. I don't remember Daphne. And the reason that I'm shocked by that is Daphne was my dressing roommate on Rocky Horror. We were very, very close.

[Quincy]

Yeah, Friends.

[Anna Gasteyer]

We are, you know, friends. So. And I don't think of her as a high belter.

[Kevin]

Well, she recalls being called in for Glinda, which was interesting news to us.

[Quincy]

No, I think you're. I think Alice Ripley told us.

[Anna Gasteyer]

Oh, Alice.

[Kevin]

Alice was Glendale.

[Anna Gasteyer]

We were all in Rocky Horror together. Me, Alice, Daphne and Leah Deliria. But that's funny. I forgot that about Daphne. I forgot that. Anyway, that's funny. So. Yeah, so that would have been OG. I don't remember Julia at the replacement one. So. Okay, but. But, but I do. I knew Julia. Julia was around, so she was probably being in that. There was like five or six of us that were like, you know, kind of considered as Elphaba eligible. So I. This is my story that I always tell young performers because as I've now carefully describe for you, I hate musical theater auditioning and I'm bad at it. And I was like, I'm just not gonna leave any stone unturned. I'm not gonna leave this situation to. Did I not do enough? Maybe I'm not gonna get the part. This. Anytime I've ever done this, it's paid off. And I tell people this all the time because maybe other people don't have the same hang up I do. But, like, when I put my head in the game, the thing is, it doesn't matter if you. Well, it doesn't. It doesn't really matter if you don't get the role because your dignity is intact. And that is that. I did that for snl. I did that for Wicked. It was like, I just didn't fuck around. I Learned the music like the back of my hand. I, Peter Fly, hired Peter Flynn to, like, literally, because I have such musical theater audition anxiety. I hired him to do, like, a simulation at Pearl. Like, we got, like, a room and I pretended to walk in and do the audition because I was like, you're behind the table and you're meeting and, you know, like, the whole thing. And it was great. It just was, like, made me do it on my feet. I sang. I sang it for a bunch of people because it's embarrassing. Singing Defying Gravity alone in a room with a piano. Like, it's. It's not.

[Kevin]

You need.

[Anna Gasteyer]

To this day, I won't do it. Like, when people are like, oh, when you sing it at our benefit, I'm like, no, it's gross. Like, it's, you know, like, there's no orchestra, there's no guards. Like, it's just kind of corny.

[Quincy]

No cherry.

[Anna Gasteyer]

Yeah, it's embarrassing. So, I mean, I have a version. I love my version that I do on my album because my first album, because it's quiet and I can sing it. Like, I literally sang at the Make a Wish gala last week. Like, it works for a lot of situations that are more intimate.

[Kevin]

Yeah.

[Anna Gasteyer]

And Seth has gotten me to sing wizard and I in lots of situations. But anyway, I. Yeah. So I just, like, brought it. I just brought it. I just. I poured myself into the audition. I knew it. I knew what I wanted from it. And. And I didn't get it. They went to. Immediately, it went to Shoshana. And Shoshana, of course, was the standby. So, like, that's pretty common. I mean, people that would have been. I probably should have predicted that, but. But it was as it should be. Like, she stood by for the part. She was ready to go, and she understood it, and that was perfect.

[Kevin]

And so did that lead you to think that maybe you need to do the stand up, standby route to principal?

[Anna Gasteyer]

Okay. No, it did not. It's a good gig. Standing by. I don't. I don't poo poo it. I just didn't think it was like, yeah, I don't think they would have put me in for that. I wasn't experienced enough, you know? And so I waited. I let it go and I was disappointed and it didn't matter. And then, like, that would have been like, October maybe. And in, I want to say, February or March, Bernie Telsey called me at home, like, not even like. Like my agents, right. And was like, hey. And I'd done Miscast a Lot and stuff. Like, that's what. Like, I said. I was like, in the world.

[Kevin]

Yeah.

[Anna Gasteyer]

And he was like, so we're. We've had huge success with the First National. Like, it was, like, a total, like, a runaway success. And obviously, Broadway is worth where it is, and we're gonna do something weird. They're gonna start a Chicago company that's never been done before. It's an original company. There'll be full rehearsal with Joe. And I was thinking that might be something you want to do. And I was like, that's awesome. And. Yeah, yeah, exactly. So there. So, like, the whole. The whole sort of moral of the story is you kind of never, like, if you do well on behalf of a situation where casting directors brought you in, and this has happened multiple times in my career, and you don't embarrass them and you leave everything on the table, it often comes back to you in maybe in a way you didn't expect, but it hasn't always, but most times. And the rest of the moral story, because the other time I did this was for Guys and Dolls, for the. Lauren Graham, remember when she was in. And the desk. Mackinac and I. They. She was. She was in. It was so irritating. They kept being like, yeah, no, they wouldn't see me. It was. It was very annoying. And they were. Yeah. I don't know why. They just. They wouldn't see we're looking for, like, someone super famous and blah, blah, which was whatever. And then she was out for, like, five minutes. They were like, lauren Graham's leaving. I think it was probably, like, a negotiation move. Sometimes they do this where they.

[Quincy]

Sure.

[Anna Gasteyer]

They actually did this to me during Kimberly Kimbote, where the musical. They're like, if you can't, like, commit 100, we're gonna go out and audition people, which is smart for them. And so I went in and, like, honestly, next to my Wicked audition, Blue, I was. I blew it away. I. I knew it. Like, they all stood up, they clapped. They were like, oh, my God. Like, you could just like, feel the excitement. And then I. By the time I got home, Lauren Graham was back in. Literally, by the time I got home, like, like, my Asian call, they're like, oh, Lauren Graham's back in. But my. The moral of that story is I've never thought twice about it. Like, I felt great about it was I did what I needed to do. I committed everything I could commit, and I didn't walk away going, if I had worked a little harder, would I have? And I just Think it's like, very comforting to put that to bed for yourself so that you can be, you know, just do the whatever. They don't all go your way, but you want to feel like, have your dignity intact. So. Because many, many other times I have not had my dignity intact and I'm not proud of that. So. Yeah, so that's so wicked. So then off we went to Chicago and it was a full blown, full tilt production, which was such a gift because, you know, rehearsal and also I just think the compare, like the camaraderie and the company vibe is very different when you begin together and you, you rehearse together and you build it together. And it just had like, instead of, for me, like, that was just very confidence building and it's a hard job. So it was, it was just nice to not on top of everything else that's difficult about Elphaba be shoved into an existing production. I think I would have lost my mind. It's really hard to be sort of cycled in and you're following in the footsteps of some extraordinary singer. You know, it's just a lot for the brain to process all at once.

[Kevin]

Was that like Elphaba comparison culture a thing yet when you were starting the.

[Anna Gasteyer]

Chicago company Broadway, I mean, I was. And people were suspicious of me. I was from television. I understood, you know, I mean, I was super hard on myself. Now I listen to it, I'm like, I was fine. Like, I don't know. But like, you know, when you're. Yeah, of course it wasn't as bad. Like, remember, the Internet was very different at that time, which is part of the reason no one knows I did Wicked, which is a little like, I still, I'm like, you did Alphabet? But yeah, I mean, we, the second a bootleg went up, they would like, cease to desist that. Yeah, there was no slime tutorial. There was no, like, it was, there was nothing. It was, it didn't exist. People didn't know unless they saw you. I mean, a lot of people saw me because it's a big show in Chicago. Was that theater is like 2500 people or 2800 massive. But it still wasn't the same as, you know, where it is now, of course.

[Quincy]

Was there any kind of like, comfort or like safety that you felt doing Alphabet for the first time in Chicago as opposed to in New York?

[Anna Gasteyer]

No, no. Only because it was like such a legit company. I mean, no, I mean, I, I, I might have, but no, I was Elphabus Alphabet. Alphaba was really Hard and that come and it was actually, it was. So I had a. My daughter turned three on my first performance. Like, on my first preview. Like, I had a baby. Like, I was a toddler going into rehearsal and I had like. I mean, it was just a really hard job. It was as hard as Saturday Night Live. It's very, very, very hard. I mean, as you know, it's physically hard, it's psychologically difficult. There's comparison culture. There's, you know, people on people. Then at whatever your little thing is like, oh, she can. She really saying, you know, all that?

[Kevin]

Yeah.

[Anna Gasteyer]

And then. Which, you know, I had enough of that voice in my own head anyway.

[Kevin]

Yeah. So talk us through learning the role in Chicago. Coming in with all of this musical theater imposter syndrome. Was it as challenging as you expected it to be, or once you were doing it, you kind of found your pocket.

[Anna Gasteyer]

The hardest part, actually. I mean, yeah, that part was there for sure, but that. But. But honestly, once you sing it and once you. It's just time on the boards, like, everything, right? Like, yeah, I don't think I really appre. Again, because I'm always going to be thought of as a comedian first. That's how people think of me because of the power of television. Like, it's just very hard to, like, unwrap that for people. You know, I tour every year. I have two albums, I've done five Broadway shows. Like, it's. It's still very hard.

[Quincy]

You're still.

[Anna Gasteyer]

Every single time. Oh, my God, I didn't know you sing. Like, it's unreal. How many people still say that to me, which is kind of a relief to be at this age where I'm like, yeah, I do. You know, like, it's not. Not smug, but like, rather just like, yeah, it's a piece of me and I get it. Like, I understand why that's confusing to people. And in fact, I've had arguments with like, my band leaders over the years because I know that I have to be funny in my shows. I know that, like 50% of the people showing up for my show, no matter what. Maybe except for in Chicago, where I had a lot of wicked fans. You know, they're showing up for a comedy show, and there's literally no thing that would be worse than coming to see a comedy show and having someone lean against about a piano and sing a ballad. Like, what a nightmare. So I tried. That's why I do, like, one ballad max, and it's gotta be earned.

[Kevin]

Although you. I would love to See your. Send in the clowns.

[Anna Gasteyer]

Yeah. Thank you. But. So that's why, like, I always. And I'm, you know, I'm a comedy person, so I'm, like, attracted to. To fun and lively music. But that's why I love performing with Seth, because we can keep it. We're very close that way. Similarly, both musical and kind of funny. Anyways, I'm not answering your question. In Chicago, the bigger things are. The stage itself is huge. It's actually a physically bigger and more demanding thing and the most difficult, which I'm sure you've heard from every Elphaba. I will say that, like, as rehearsal went on, I was like, oh, I think I can sing this. Like, I'm not that worried about. It's just such a mountain of. Of material. You're not really even like, questioning yourself. You're just. You're just trying to find the placement and find it, whatever. I didn't know the word sport then, but that's what I was doing. Yeah. And I was training and I'd been singing. It wasn't like I was a total neophyte. It's probably more things like, until you sing the role, you don't realize the burden of the eight a week. You don't burden. The smoke and fog is a shit show, and it will always be. I mean, there are. I am one of them. There are a lot of singers. The fog, the minute it comes into the room, cuts your voice in half. There's just something really physiologically challenging about fog. There's like a. People go, oh, no, it's just propylene glycol. But it's this. Like, you can taste it. Like, it's like a film and it. It gets in the way. Like, if I'm. If I'm at, you know, live at Kelly and like singing, you know, a Christmas song and they pump that fog. Lighting designers love it because it looks so good, right? I'll be like, whoa, whoa, whoa. Like, I can feel it the second. This is like the one thing. So that's something that's super challenging. And, like, there's just other things like that, the weight of the dress, the physical exhaustion and whatever. It's Chicago, right? I had a baby. Like, you get sick and singing through being sick and singing through sinus problems and singing, like, just all that stuff. That is probably what I remember the most in terms of just like sort of the day to day Olympic athlete challenges. Like, you know, like, like whatever Megan Hilty's going through right now, like, you know, in Death becomes her. It's just very physiologically difficult. And those scores are written high. They're probably written too high, if I'm being honest. They're not. They're amazing, but they're. They're not. It's not norm, because it's really screaming, no matter how healthily you do it. And there's people that learn how to place it. I'm one of them. Where it sounds pretty safe or whatever, but it's. It's not really how the voice is set up. I mean, you know, Ethel Merman was. Think about it, hitting a B. Those were all of those, like, high notes in, like, Gypsy or whatever. That's a B. And now it's like a regular F and G. I mean, that's right. Super, super high. So I think it's just hard on your body. Like, it's hard.

[Kevin]

And how did you go about crafting the character? Because something that has been a through line of a lot of the actresses we talked to who played the role is they point to you as. As being the actress who unlocked the comedy in Elphaba and, like, showed them that. Elphaba, huh?

[Anna Gasteyer]

David Stone likes to say that.

[Kevin]

Yeah.

[Quincy]

Yeah.

[Anna Gasteyer]

I mean, I think that the role is written funny. I think. I think she's. I think that people who are defensive are funny often.

[Quincy]

Yeah.

[Anna Gasteyer]

I mean, she can come across as a real nudge, Elphaba, but she can also, like, if you look at it differently, like, it's a funny defense mechanism. And I think that's what that. Joe. Joe is funny. Joe's a funny person. And so I think it just kind of came and tell, and so it just came organically. I mean, I think probably the harder part is. And I understand this when you're developing something, Kristen was the funny one and Adina was the earnest one. You know, like, that was just like. They're trying to distinguish the two characters. But the thing that I really. Kate is very funny. And we were. We're still very close. I mean, we were literally texting yesterday. Again, my closest friendship have all been developed through laughing together. Like my best friends in high school, my, like, girlfriends, if I think about that, like, people that I've laughed very hard with, had common ground with. So for us, I think that was just a way in. And she's like a very pragmatic little gal, that Kate, you know, and she has her. Has her hair, little, you know, voice. It's so funny with all the glindas because they tell you always makes me laugh because they say something Very serious with that very high voice. But, you know, early on, she was like, we're playing best friends, so we're gonna be best friends. So we. It was like. She pronounced it, so I was like, okay, great. And we were. We were best friends. We were really good friends. We got along really, really well. We. We led a company out of town, which is its own animal, which I think was a gift, actually. I think it was sort of unfettered with, like. We'd have, like, a lot of, like, fingers in the pie. We had, like. We. We rehearsed and then we did the show and, like, Mark Platt came in and saw it and left, like, every. There was not a lot of, like, tinkering.

[Kevin]

Yeah.

[Anna Gasteyer]

So I think we found the connection through Elphaba's sense of humor earlier. And that's nice that people credit me with that, but I wasn't like, a planned thing. I think it was just, like, a way in and a way for her to be a little more likable, frankly. I mean, like I said, she can be a real pill. Otherwise kind of green. Green bummer, you know, you have to understand, like, why, like, that's. Yeah. I just think it's an easy way in. The hard thing is, for me, and I think it was for a lot of people, Adida is, like, such a. An original. Like her. Her. Her. Her breath is insane. And her. The, like, speed, like, the notes that she sustains and her sort of lung power. And they were so emphatic because, again, we were early. We were following in her footsteps.

[Kevin]

Yeah.

[Anna Gasteyer]

That we follow her phrasing to the teeth. And that was just sort of like a. I think Stephen L. Remus was young, and I think everybody was just kind of like, finding, you know, what they wanted from it. So I was told at my audition, which is insane, that if I breathed between me and. I'll stand there with the wither. So with me and I'll stand there with a wizard. He was like, if you breathe between these notes, you will not get at this job.

[Kevin]

Wow.

[Anna Gasteyer]

You told me that. So there was such like, specificity to what they were doing. That was Adina specific, you know? And she. She is. I. I have a sort of deeper belt than she does. She has a higher sort of. I don't know, more elastic. Yeah, yeah. Pingy elastic belt. So it's really hard. It just requires more. A different use of air, quite frankly. And so. And Chicago was huge. And it was actually more steps down stage to get down there with that stupid suitcase and 500 pound, suitcase and like, full of gold. It felt like it was like, full of, like, golden bricks. So it was just physically weird to try to, like, find. And her phrasing was just specific to her. That. That's really what it is. That is true, by the way, of all Broadway shows. You're always. That's why the person who originally. I mean, I had this with mattress where I was, like, trying to unpack what. You know, finding your own performance takes us. Takes a beat, you know, outside of what somebody else has done. So. But in the case of Wicked, Idina, so specific, A and B, it's orchestrated within an inch of its life. So you are constantly, like, your lines are falling in between at other people's pacing. There's very little dialogue that's not underscored in that show.

[Quincy]

Right.

[Anna Gasteyer]

So it's. It's tricky. And then on top of that. And it was funny because when we all went back, I went back to see it at the 20th, of course, and I went like. I took my. I've taken my kids over the years, and It's. It's like 11 minutes faster. It's so much faster the show. So they are like. I mean, that's real oxygen for an Elphaba. You know, that's somebody who's, like, not holding something as long. And I listened to our tempos, and I'm just like, oh, my God, that was so much slower.

[Quincy]

Yeah. So that's interesting.

[Anna Gasteyer]

Yeah.

[Kevin]

So then how did Broadway happen?

[Anna Gasteyer]

I mean, by then there was a pipeline. Right. So we were. Right. So Shoshana went in, Shoshana left. I think Eden was standing by for Shoshana. Eden came in, and then I left Chicago and I did three penny Opera on Broadway. And then as soon as Threepenny Opera left, I went into Wicked.

[Kevin]

And you wanted to do Broadway after your Chicago experience?

[Anna Gasteyer]

Of course. Yeah.

[Quincy]

Were you. And by that point, were you feeling in control of the role?

[Anna Gasteyer]

Oh, yeah. I mean, I played it for a long time in Chicago, so I loved it. I mean, it wasn't. I'm speaking negatively, it probably sounds that way, but it was not a negative experience. It was an extraordinary experience. I mean, you know, there were hard things about it. Like, it's easy for me to remember the hard things. A, physically hard, but B, the other thing is, if we were the only game in town. Right. For. In Chicago. So that was. And I. Again, this is just, like, lesson learned. Like, we. We were doing press all day every Monday. I mean, it was relentless.

[Kevin]

We're launching it.

[Anna Gasteyer]

Yeah. And it was the biggest. It was the biggest fish in town. So we would do, like, the Halloween, like, Chicago Halloween parade, the Chicago St. Patrick's Day Parade, the Chicago, you know, sing at the national anthem at the White Sox game. And it was just. It was all really, really fun, but it was, like, very constant. And so there's just kind of no. I mean, there's no rest for the weary in Broadway anyway. But, you know, New York's easier. You're home.

[Quincy]

Yeah.

[Anna Gasteyer]

You're. You're. You just zip into work and back. Like, it's just not as. It's still hard, but it's not as. It's not as, like, unrelenting as opening something.

[Kevin]

It's interesting because when Stephanie talked about launching the national tour, she said she felt like it was an opportunity for her. They gave her the freedom to kind of craft the role to her needs and not have to copy Adina. Did you feel like you were offered that either in Chicago or Broadway?

[Anna Gasteyer]

Well, I mean, I think that's what you're referring to with regards to, like, finding the comedy. Like, I wasn't necessarily thinking of that as, like, an opportunity or not. That was just, like, me coming in and doing. Obviously, they're hiring. You know, everyone's going to be slightly different. And. And Joe was very creatively. Joe's an actor's director, so he's gonna see that in a performer and. And like it, you know, So I definitely wasn't feeling, like, shut down. I guess that's true. I wasn't let. Somebody was like, no, no, no, no, that's not funny there, or whatever. I wasn't, like, scheming, like, how am I gonna make? Or anything like that. Yeah. And this. And. And this conversation is like, I was very concerned about filling shoes as, you know, so that was maybe my bias a little bit. Like, I wanted to make sure that I was delivering and that I. And that it was earned, you know, so maybe that I might have put that on my own shoulders more than Stephanie was in that story, because Stephanie had been there, you know, a long time and probably understood the role and was like, I want to. I want to make a mark. You know, I get that I was. My mark was just, like, proving to the entire Broadway theater community that I could sing like that, you know, and do it eight times a week. That. That was a much higher bar for me than it was like putting a spin on Elphaba at that point, you know?

[Kevin]

Yeah. You mentioned the preconceived notions that you were feeling from people Prior to taking on the role, once you were up and doing it, were you getting any pushback or did you feel a general acceptance?

[Anna Gasteyer]

WOMAN My reviews were really good, which helped. You know, of course, once that happens, you're usually like, okay, well, I'm not a joke. No. And people came and stuff like that. No, I feel like I. I mean, I. It's. I do feel like there was a healthy skepticism of television people, more so than now. You know, I think there was like a. And I get that. I do have to say I really do get that. It is so hard to become a Broadway performer, and they continue to be the hardest working, lowest renumerated people. Even if the. Even at the big bucks, even at 10, $15,000 a week, which is a lot of money on Broadway, it's so much less than those people would be making on tv. And they're confined to one job and they have to sleep all the time, and they have to live like nuns. And, you know, it's. It's. It's a hard job. And I think. But I think if you are good at is literally like a calling. I mean, it's. You know, singing with other performers on Broadway is the happiest that I. Because it's the one thing, like, if you're born being able to sing, I imagine, and to dance, I. It's something, you know, I'm not a religious person at all, but it is God given. It comes from something outside yourself, and it's a. It is a bigger thing. So to be sort of like, in harmony and connection with other musical theater people is, like, such a natural high. But it's hard, man. But I also can say that, like, when you're really in the flow, like, when you're in, like, I don't know, tech for something that's, like, pretty good, that's about to open, and you're like, I think this is gonna maybe be really fun. You know, whatever the, like, legacy, robe, ceremony, like all those little things that, like, bring people together. It's a club that you can't. I would imagine my son is a competitive runner. Like, you can't define it for other people outside the club. Like, it's. It's. It's. It's just a weird thing. You were born with a mutant skill, and you've met your other mutants. And so I definitely know that I'm a part of that now. I mean, it's been a 20 year. You know, I took 14 years between Broadway show number four and Broadway show number five. But I did you know all those televised musicals? And I've, you know, done albums, and I've toured, and I've. I've done it enough that I know that I'm. That I. I have a gift that's Not. That not everybody gets and that I have to take advantage of and that I'm lucky to have and that there are people who are better at it than me, but that my baseline is pretty high, you know, So I don't know. Comparing is sort of boring at this point in my life because everybody's offered, like, a different I. Maybe I'm. I can tell a joke better than Adina, but I can't hold a lot a note as long as Adina, so it's like everybody's. And we're all kind of within the same. I've never. I've never on Broadway ever felt like. And I really want to say this, like, I've never once lost a role to someone that I felt it was unfair to lose it to. Except for maybe Lauren Graham. I take that back. But I think she's fantastic as a. So I guess I'm officially one of the people in the club. But. But in those Broadway rooms, predominantly, like, you're never. Like, if you hear it's Stephanie Block that got the role, you're like, oh, yeah, okay. Yeah, yeah. Oh, it's Alice. Oh, yeah, of course. Of course. Like, it's just. It's so given. Like, it's so freaking hard. Of course.

[Kevin]

Wait, what is your falsetto story?

[Anna Gasteyer]

Oh, it's so embarrassing. The reason that it's embarrassing is not the reason that it's embarrassing. It's. Again, it's back to, like, don't go if you're not ready. So I did. I did all four readings of Freaky Friday that they were Tom Kitt and. And Brian.

[Kevin]

Oh, the musical.

[Anna Gasteyer]

The musical. Yeah. And it was so fun. It feels beautiful. And I thought it was, like, gonna move. Okay. And on the last.

[Kevin]

I love that.

[Anna Gasteyer]

The last reading. I know. It's so good. The last reading, they were like, oh, yeah, we're not gonna come into Broadway. We're only gonna be regional. Sorry, was nobody clear about that with you? This is just for licensing. Like, no, nobody was clear. That's kind of a drag. I have small children. I'm not going to the Cleveland Playhouse. I can't do this. You know? Like, I mean, not like, I don't want to go to the Cleveland playoffs, but I was just kind of like, this. Had a bigger plan anyway. But it was. It's a beautiful. The music is fantastic. And I love Tom and I love Brian. I mean, it was a really fun experience. And I love the people at Disney, to be honest. Those executives are incredible over there. So, anyway, as you can imagine, it's a giant role and you're really, really busy. And they. So backstory. Sorry. I told this story out of order. I had been offered the mother in New Brain that we did at City center center with Jonathan with Groff Sauce. Okay. And I. So that was already happening. I was going to be doing that then in the summer, and in the spring, I was doing the Freaky Friday workshop, the 4th. And so much music. So much, you know, singing your balls off, like, Elphaba level like that for a week, belting. And they called very. It was maybe, like five days. It wasn't a lot of time. And they were like, hey, they want to see you for falsettos. And it's just going to be Bill Finn, James Lapine, who had just cast me in A New Brain, right? And Jordan Roth and who'd given me my first job, which was rocking horror. And I was like, I can't learn. I'm breaking down. I'm doing the Freaky Friday workshops, like, all week long. I don't have time. And this is. Again, we're like, this is such a life lesson, such a lesson learned. And by the way, I think audition stories are worse than hearing the stories of people's dreams. But it's like, at that level. So I. I'm mortified that I'm sharing this. I've now said so many things that I should just start over. But anyway, yeah. So net. Net. The. The. The moral of the story that I will continue to say throughout the story is don't go in if you don't feel like you can. Like, if your gut is telling you you're gonna chunk it, don't bother. Like, there's the voice in the back of your head. I know that, like, you can't be predictive, but it's never in my experience. Your gut is always gonna win over your head.

[Kevin]

Right.

[Anna Gasteyer]

And especially because we've all established that I have something of an imposter syndrome and I'm bad at musical theater auditioning. Right. So I especially don't have, like, the gods on my side on this one. Right. It's not like I'm going to go in and wing it. Like, look, if I'm going into, like, a TV comedy audition, I'm a comedian. Like, I can. I know that I'm going To improvise. It's probably going to be funny if I'm charming in the room, you know, where that doesn't work. Okay.

[Kevin]

Breaking down. You need the beats down. You need to know what you're doing.

[Anna Gasteyer]

And here. And it was agent I was with for one year, and I literally went right back to my old agent as soon as this happened. She was like. Like. He was like, oh, just go in. It'll be fine. Tara Rubin says it'll be fine. I was like, okay. So they are like. They call. They're like, well, you can go. I was. And I called again. I was like, I don't know this song. I don't feel prepared. I. I really don't know this song. And this is, like, a really hard song. And I mean, you know, it's. It's just an acting song. And it's. It's also just not like.

[Quincy]

It's a very specific music.

[Anna Gasteyer]

Send in the clowns. You know, it's not. You know, so they're like, bring your book. And I said, I don't have a book. Okay. Famously, I do not have a book and have shared many times that I don't have a book. You know, so they're Just go. Just go. So I go an hour early. I meet with Vadim. I'm terrible. I barely know the song. I'm panicking. I'm. You know, I'm already like, did you.

[Kevin]

Just have to do Breaking down, or did you have to do holding to the Ground, too?

[Anna Gasteyer]

I just had to do them Breaking Down. Okay, but Breaking down is like 18 pages. 15.

[Kevin]

A journey.

[Anna Gasteyer]

A lot of pages.

[Quincy]

It's a lot play.

[Anna Gasteyer]

Yeah, it's right. So I go. And I go, listen, I just want to put this out on the table. Like, I. There. You know, I'm not. I'm truly. I. I'm not prepared. I don't know this. I've been in a workshop. I just want to apologize in advance. Right? And they're like, don't worry about it. Don't worry about it. Don't worry about it. What do. What do you have in your book? Just sing something from your book. I don't have a. I know. And by the way, it couldn't sound like a bigger, like, dick. Who's. What? It's not that I am proud that I don't have a book, by the way. I just don't have a book. Like, it's just a fact. I'm. I'm embarrassed that I don't have a book. I didn't Go to musical theater school. I didn't go to Carnegie Mellon. I didn't go to ccc. Ccm. I didn't go to Michigan. Okay. I don't have a book. I don't have a book. I sang Caro Mio Ben to get into Northwestern. Like, that's. I sang an art song, Unmoto de Joya. Would you like to hear that? So. Right. So mortifying. So they're like, what, do you want to just sing something from a show you've been on? And I. I'm panicking. I'm in, like, flop sweat. And I'm like, what. What am I gonna sing from a show? So you know what I say? Which makes no sense. I don't think I. I. Jonathan Croft spit tape. When I told him this, by the way, they were like, what's the first musical you ever did? And I was like, annie, get your gun. And they said, what do you want to sing? I was like, moonshine Lullaby. Why? So I sang Moonshine Lullaby, which I love. It's one of my favorite songs. But I was like, what. Why am I doing this? What's. And as I'm doing it, like. Like, under boob sweat, underarm sweat, back of neck sweat. You know, like, when you feel something dribbling down behind your ear, like, that's adrenal. So as I'm doing it, and I'm just panicking. I'm flushing, I'm turning red. And then James, they're like, that was nice. Moonshine Lullaby is nice. What is happening? What am I doing? And then James Lapine goes, why don't you sing something from Wicked? Let's hear you really sing. Like, what you sing. He's looking at my resume, by the way, while you sing. And P.S. i've known James Lapine. James Lapine. I did Passion. I did Stephen Sondheim show in Chicago at Chicago Shakes. And James Lapine flew out to see it because he had read the reviews, and he was like, I. He stayed after to meet me and was lovely. He was like, we have to work together. Blah, blah, blah. So it was like a room. And he had already cast me. This is where my brain is. I'm like, oh, my God. They're gonna realize that I'm a charlatan, and they're gonna regret that they cast me. And they're gonna call Jonathan Groff and be like, who do you want me as your mother? Because it's not that, you know, like, that's. That's where my brain is, like, in this process. So. So that's why the. Hence the sweat and the moonshine lullaby. And I'm, like, going, you know, getting worse and worse and worse. And then. And then it was the greatest thing. The guy goes, let's do. Let's do. It was. It was wizard and I. I was like. He was like, can you sing something? Just play something from. To the accompaniment, like, place. It was. It wasn't defying gravity because it's too hard to get in with the. I hope you're happy now and all that. He's like, I. He's like, how about wizard and I? So he starts playing the wizard and I. Are you ready? Dun dun, dun. No, it was literally with me. Stops. I don't know the rest. Oh, my God. Just stops. Like, okay. Then it's like, great, so let's try on breaking down. Why don't you just read it? I was like, I don't think it's a good idea, but. And they're like, why don't you just read it? And it was exactly like, what you would imagine. I had no idea what I was doing. All pages fell off the. Off the music stand. Flew all over the room. All of it. I mean, every single part of it. I was like, beat red. At this point, I was like, you know what? I'm not gonna waste your time any further. This is so humiliating. I have never. I'm so sorry. I started to, like, gather the pages off the floor, like, all in there. All. You know, I'm, like, bundling them and running. I couldn't have gotten out of there faster. I was, like. Like starting to cry at this point because I was so mortified. I was like, let me just come back another day. Like, can I please just come back another day?

[Quincy]

This.

[Anna Gasteyer]

This is so. I knew I shouldn't have come in. I'm so glad that I did this. And by the way, she's never called me in again. What a surprise. So, I mean, I was. It was a disaster. I left. I went to H and m. I spent $200. I literally walked out of her office. Walked immediately into H and M. Blackout. I know. Literally. And then I went and had two martinis. It was, like, all I could do. I was like, by the way. So the whole audition cost me. Shame. Two martinis and 200. So awful. It was really, like, the last music theater audition I've done. And now that I'm thinking about it, and then I did a New Brain. And then Bill and. And then. Oh, and then I called my agents. I was like, can I Please go back. And they're like, yes, yes, yes, they'll have you back. And then I called to follow up. They're like, they cast Stephanie Block. I was like, perfect, cancel.

[Kevin]

Cut.

[Anna Gasteyer]

Which is fine. Stephanie was fantastic. But it was phenomenal. It was bad. I mean, the moral of the story is just like, I. I don't know. Like, I feel like, for me, there's already enough demons in there. Like, you don't need to add to the pile. Thank God. A new brain was one of the high. My creative highs. It was one of the best experiences I've ever had. So it was. Every part of it was great. Like, not just how good the show was, which it was. But, yeah, James was incredible. Bill was incredible. Like, everybody. Everybody was very. I'm. I felt it was redemptive, you know, I, I, I. I did not get in my own way. Yeah. And I didn't. I didn't let it. I was like, I'm just not gonna. What can I do? Like, I blew it. So let's go just, like, be at a beautiful show and have a great time. Which we did.

[Kevin]

Totally. Okay, before we wrap up, we have to ask you.

[Quincy]

We have two questions for you. Can I ask a question first and then you ask for a question?

[Kevin]

Yeah.

[Quincy]

All right, so something that a lot of Elphabas tell us is that they are waiting for their moment to return as Madame Marable. Is that something you would consider?

[Anna Gasteyer]

No. Never, ever play Madame Marble. First of all, like, famously, Seth Rodetsky and I have covered this so many times. No, it's like, a bit like, I'm like, no, no, no. It's like playing, like, Mama. Bryce out. Pass. Ask yourself.

[Kevin]

Breathe new life into the role.

[Anna Gasteyer]

What would Bernadette do?

[Quincy]

What would Bernadette do?

[Anna Gasteyer]

She would never play Madame Morrible. Patty would never play Madame Morrible. Do not play Madame Morrible. Hell, no. Oh, my God. I mean, I understand why people play it, and I thought Rondi Reed was unbelievable. I mean, unbelievable in our performance. But I. No, no, no, no, no, no. Also, people have been trying to make me play Madame Moral. Like, it's. It's like even doing Queen Agravine, I was like, ah, it's. It's a comedy. I have. So kind of what you were asking all along is like, I. So I sang Elphaba, but it. At the end of the day, people just. All I really still get offered is like. Like, after Elphaba, I was offered RAs in 9 to 5. You know, like, things like that where I'm like, yeah, no, I didn't sing Alpha, but I play Ross. Like, I could have done Ross. There's nothing wrong with Roz, by the way. But, like, in terms of, like, carving your own terrain, right? Like, I was not vocally doing what I was doing in order to do that, you know, I mean, I'm a little mellower about it. Like I said, Queen Agravaina was like, awesome fun. I get to like, is there a.

[Kevin]

Part of you that wants to do a hyper dramatic role on Broadway?

[Anna Gasteyer]

Maybe vocally? Yeah, maybe. But I mean, like, it was great. I played Fosca, like I said, and there. There are some roles like that that of course I would want to play. I mean, everybody wants to play Mama Rose. Everybody, you know, everybody wants to play. I don't know about hyper dramatic, but, you know. Yeah, music. Music's different. Music's so emotive. But I'm. I'm happier. Yeah, I don't think I would want to play Madame Morrible. In summary.

[Kevin]

Good.

[Quincy]

I love that for you. I love that for you so much.

[Kevin]

Okay. Are you a wizard and I defying gravity or no. Good. Eat Elphaba. It can mean whatever you want it to mean. All we ask is that you explain why.

[Anna Gasteyer]

Well, no Good Deed's my favorite number in the show. Far and away. It's the easiest placement. You're warm already. You're hot in the show. The Fury is really easy to access. I feel like it's such a great marriage of a song and intention. Like, it's. It's. You know, I'm writing a musical right now, and it's like very. When you find those moments that are a song that is such a incredible storyteller. I mean, they all. Are all three of those songs. He's a genius, but that way. But nogadid is. It's such a turning point in the story. It's such a. It's such a huge turning point in the story because you have to be on Elphaba's side as she turns wicked. You have to understand really where her sense of betrayal and frustration comes from and that so much of it is coming from love. And I think that song does that really beautifully. Extraordinarily, actually.

[Kevin]

Are you writing a musical for you to star in?

[Anna Gasteyer]

Sort of. Rachel Dratch and I wrote a parody of the Hallmark films a couple years ago called Clusterfunk Christmas that was on television, and we are developing it with Jeff Richmond into a musical, a holiday musical. So we are playing. We're not. We're like the B story. We're not the stars because we're not young, Hallmark speaking people, but it's really fun.

[Quincy]

Yeah, that's awesome.

[Anna Gasteyer]

And then I also have this character, September L. Davis, that I've done for the last gazillion years. And we've written her apology tour, which is a show that I just tried out for the first time last week at Ars Nova. And we're developing that possibly to come here, which would be incredible. And that has original music from fake musicals.

[Quincy]

So that we've written.

[Anna Gasteyer]

So we have Tom Kitt wrote. Yeah, Tom Kitt and I wrote some of them. And Sam Davis, who's an incredible orchestrator, wrote some of them. So we have numbers from Hindenburg and a show called Death Race and a fake Lin Manuel show called Quantum, a song called Quantum Love from String Theory and all. We have all these, like, fake songs that are fantastic. So that would be. Yeah, that would be fun. I mean, I'm definitely starring in that because this character is a. A very problematic diva who. This is her amends tour. She's making amends as she pursues her sixth Tony.

[Kevin]

Thank you so much for coming on. I love your passion for the theater community, and it was so fun to talk to you.

[Anna Gasteyer]

I love theater and I love show folk, so I possibly will never be called in for another audition after this conversation. And it was a great goodbye to the theater.

[Kevin]

You had a good run.

[Anna Gasteyer]

I'm not getting morrible. That podcast not coming.

[Kevin]

We're just waiting for the first Alphabet to go back as morrible. Yeah, someone's gonna do it.

[Anna Gasteyer]

Has no one done it yet?

[Kevin]

No, but the time is coming.

[Anna Gasteyer]

Do they all want to do it?

[Quincy]

No, but some of the more recent Elphabas say they would like to.

[Anna Gasteyer]

More recent? Oh, they're too young. You know what? When you hit 40, you start thinking twice. Hilarious. All right, friends, be well.

[Kevin]

Thank you so much. It was so nice talking to you. You've been listening to Sentimental Men.

[Quincy]

We'd like to say a big thank you to everyone at the Broadway Podcast.

[Kevin]

Network and a special thanks to Michaela Reynolds and Julia DeMarzo, our photographer and logo designer. You can find Sentimental men on Instagram, TikTok and X Entmenpod, or you can.

[Quincy]

Email [e-mail] till next time.

[Kevin]

I'm Quincy.

[Quincy]

And I'm Kevin.

[Alan Seales]

Hey there. I'm Alan Seales, host of the Theater Podcast, a weekly podcast that takes you behind the scenes with intimate personal conversations that include the biggest stars on Broadway, TV and film. My podcast has over 350 episodes with guests including Stephanie J. Block, Kerry Butler, James Monroe Iglehart, Andrew Barth Feldman, Alex Brightman, Patti LuPone, Ramin Karimlou, Brian Stokes Mitchell, and even TV star like Isaac Mizrahi, Ariana Maddox, Michael Urie, Eddie Izzard, and literally so, so many more. My guests have spilled secrets, told coming out stories, discussed their fears and successes, and even had huge epiphanies live in the episodes. So you're bound to hear some things from my guests that you've never heard anywhere else. I've also got many deep dive takeovers on the podcast, which are consecutive episodes dedicated to cast and creatives from a single show like the Outsiders, Back to the Future and Juliet wicked, Beetlejuice, Hadestown, Frozen 6. I could go on. Can you tell I like theater? I've definitely got something you're going to enjoy, so go ahead, search for your favorite star and listen to their episode. You can find all the info about the podcast at BPN FMTP on the Broadway Podcast Network or anywhere podcasts are found. If you need that link again, it's BPN FM ttp.

[Anna Gasteyer]

Take a deep breath. Make the world a little colorful.