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Alison Stewart
This is all of It. I'm Alison Stewart live from the WNYC Studios in soho. Thanks for sharing part of your day with us. I'm really grateful that you're here on the show. Today will mark the 250th anniversary of Thomas Paine's revolutionary pamphlet Common Sense with Julie Silverbrook. She's the vice president of Civic Education at the Constitution Center. We'll also talk to musician Don Was about his new solo album and preview his show at the Blue Note Jazz Club on Monday. Plus two conversations with folks nominated for Golden Globe Awards and they're happening this weekend. Tessa Thompson, who is nominated for Hedda, and director Park Chan Wook, who is nominated for his film no Other Choice. That's the plan. So let's get this started with a show about ambition. Imagine a series of short stories brought to life on a Broadway stage featuring bold faced named comic actors while the New York funk band Lawrence provides music along the way. That is what you will find at All Out Comedy About Ambition. And it is ambitious. The sets are by Tony nominee David Korns and it's directed by Tony winner Alex Timbers, who has four shows running on Broadway. Seventeen actors are rotating through currently on stage. You'll find my next guests in Starring Rose, Cecily Strong and Beck Bennett. It's nice to meet both of you.
Cecily Strong
Hi, Nice to meet you.
Alison Stewart
Nice to meet you. And joining us is the writer of All Out, Simon Rich. Hi Simon.
Simon Rich
Hey, thanks for having us.
Alison Stewart
All Out Comedy About Ambition is playing at the Neatlander Theater. You did a version of this, Simon, called All In Comedy About Love. Why did you want to take on Ambition?
Simon Rich
It's just something I've always been gravitated to, characters who are very ambitious but don't quite pull it off. So you'll find a lot of characters in this show that, for whatever reason, never quite got the esteem or respect that they hoped for. One characteristic story is from the perspective of Paul Revere's horse Otzi, who is the person who Paul Revere rode during his midnight ride. But sadly his contributions have been lost to time and he's extremely bitter about it. And those are the sort of characters that I really enjoy writing about.
Alison Stewart
I liked Otzi Personally, when I saw it, how did you get. How do you describe the show, Beck, when you describe it to people?
Beck Bennett
I go like that. First, I say, yeah, it's. It's a. It's like kind of like SNL on Broadway a little bit. It has music. It has these short stories which are like sketches. It's kind of like a performed reading where we are. We have the books in front of us. We aren't like, off book, but it is fully staged. You know, there's so many things happening. There are these, like, drawings behind us. Lawrence is like this intoxicating energy. It's. It's so fun to be like. It's kind of like a musical in that sense. But we don't get to do. We get to enjoy being on stage and reading Simon's words, which are so funny. And we get to feel like we're in a musical with this band all around us, and it's really fun.
Alison Stewart
Cecily, how did you get involved with this?
Cecily Strong
I saw all in last year and loved it. And this came around and I jumped at the opportunity. And I'm filming another show in Toronto right now. But I was like, we are carving out time. I'm doing all out. I am gonna be a part of it this year. I'm not pregnant anymore, so I was lucky enough I got to jump in this year.
Alison Stewart
Well, congratulations on having the baby.
Cecily Strong
Well, thank you.
Alison Stewart
How did you get involved, Becky?
Beck Bennett
I got an email from my agents.
Alison Stewart
It's good to open your email.
Cecily Strong
Yeah, it all starts with an email, folks.
Beck Bennett
Yeah. And I was like, simon, write that. Yeah, write that, Simon. We could put it in the show tonight.
Cecily Strong
I don't know.
Beck Bennett
Something improvised, maybe. That would be great. But, yeah, I was at SNL when Simon came back as a writer when John Mulaney was hosting, because he. He was writing there with him a lot. And that's how I met Simon. And I did a short story of Simon's a while ago for Audible. And so, yeah, I knew him and we've worked together before, and I jumped at the opportunity to do it again.
Alison Stewart
Simon, you said of writing that the delete button is your friend, but you can't delete performances. They're up there for people to see. What did you learn from that previous experience with all in that you were able to use in this show?
Simon Rich
I mean, I think the thing that's so thrilling about. About these shows for me is just how elastic it is. Every single comedian is so talented, but also very distinct, and they all bring something completely different to The. To the. To the roles. And so it's thrilling for me to get to work with. With such talented performers and. And to see what interesting directions they take. The material, it changes every week and then. And that, that, that. The fact that it's that dynamic, I think is really cool.
Alison Stewart
Why did you laugh at that?
Cecily Strong
Oh, because I'm just thinking about even when I've been there, like, last week we had Ben Schwartz, and Beck and Ben are so different. And it's been fun for me to be next to it on stage, watching. And now we have. It's Jim Gaffigan's last week, who is outrageous and so much fun. Makes me laugh so much. And then Mike Birbiglia is coming in, and I'm like, they're very different energies. I can't wait to see what Mike does. You'll get to see a little bit today.
Beck Bennett
Yeah, you got a put in rehearsal today right after this.
Alison Stewart
Oh, that's gonna be exciting.
Cecily Strong
Get a little mic for Biggs preview.
Beck Bennett
Yeah, that's all exciting and it's wild. Like, I did my first show on Tuesday, then today is Friday. Like, it feels like a week has gone by, but that first show, I'd only done it once with Cecily and Wayne. I haven't. Hadn't even done it with Jim, so. And now I'm like the expert after three shows because it'll just be me, Mike and the. The other understudies, so. Yeah.
Alison Stewart
So you took over for Ben Schwartz, right?
Beck Bennett
Yeah.
Alison Stewart
Did you see the show with him in it?
Beck Bennett
I did, I did, and he was amazing. And I love Ben. I know Ben. And so it was. It was interesting seeing the show and being like, okay, I'm doing that, but do something different. But what he's doing works so well. Figure that out. So, like, do that, but different. Do it your way.
Alison Stewart
Yeah. As a new kid on the block, what did you have to learn?
Beck Bennett
I think I had to learn. You know, we have these teleprompters out there, so it's kind of like, because we aren't off broadcast, but we also have the books in our laps, I had to learn the sort of dance of watching the other performers and staying engaged with what's happening. Also keeping my place in my book in case anything does happen with the teleprompters, but also keeping my place on the teleprompters out there and sort of like that and not losing my place, just being engaged, because it's very different. You know, being fully on cards, like at SNL is one Thing, you can read everything, but with this, you're kind of going back and forth and you don't want to lose your place. It's different than being like. It's easier almost to be fully on cards and fully memorized, but to kind of go back and forth between the two is a little bit of a dance that I had to learn.
Alison Stewart
How did you learn to use the book, Cecily?
Cecily Strong
I think. Well, Alex, in our rehearsal gave a great note that was sort of, if we're talking to each other, use the book more and then speaking out. But I really, even after a week and a half, this old veteran here, I feel like. I know I'm very comfortable with it now. And you really do start to know it, which frees us up to be a little bit looser. And it's been different every night. It's very exciting. It's what live theater is supposed to be.
Simon Rich
I've always wanted to do something that was like snl, that had that. That rapid immediacy, but took place much, much earlier at night.
Beck Bennett
Yeah, it's like the experience is like snl, but it's so much more decent and just more relaxed and just enjoy.
Cecily Strong
I can walk in heels a little easier. I'm less of a baby deer when it's not 1am we're talking about the.
Alison Stewart
Show all out comedy about ambition playing at the Nederlander Theater. My guests are actors Cecily Strong and Beck Bennett, as well as writer Simon Rich. When did you write these stories, Simon?
Simon Rich
These stories, the earliest ones are, like, it's hard to believe, are about 20 years old, really. And the most recent ones are from around this year or last year. And, yeah, it's doing these compilation shows all in and all out. It's really fun to revisit past material. Much of it does not hold up, I found, but you can just delete those and. And it's exciting to throw some in that still work that are, at this point, a couple decades old.
Alison Stewart
Okay, for the essay question, do you have to be ambitious to make it in New York City?
Simon Rich
I guess. I don't know. None of these characters really do make it, but they certainly try, for better and for worse.
Alison Stewart
Beck and Cecily, when you're thinking about these stories, they're sort of fable, like, in many ways. What did you think about ambition when you heard these stories? Did it change the way you thought about it? Did you think about it differently before? What do you think?
Beck Bennett
I mean. Go ahead.
Cecily Strong
Well, I was just gonna speak specifically. Simon writes this piece from New York City's perspective. And it really. I've had so many people, and I get to read it, which is very nice. Thank you, Simon. I don't know if I've told you that, but I get all these great comments from people afterward, from young to old, to say, like, it moved them. It made them cry. It's just everybody can see themselves in it. And I think that's. It's. It's so nice ending with that piece because all of us, especially living in New York, I do think you have to be ambitious. And it's all about, like, what do you put up with in order to be in New York? Like, this is the life that you're choosing. And a lot of times it's for. For us, anyways. It's to be in this business of the arts, and it's sort of everything that the city throws at you. And I had a friend see the show two days ago, and he said he was like, you really. You got New York right. And not many people do. And you guys, you got it right.
Alison Stewart
Yeah. It's interesting. When you play New York, you talk about how well people take advantage of New York. We'll just say in certain ways. How do you get into the mindset of New York as you're getting ready to play that role? Because you are closing out the show.
Cecily Strong
Yes. Well, it's sort of. We. I like to think of it, like, going in like it's like supervillain, but then it's like. But then the supervillain, who's also impressed by their adversary, which are the young people who make it in New York.
Alison Stewart
I kept thinking of that New York Times piece, or was it in New York magazine about the West Village girls?
Cecily Strong
Oh, yeah.
Alison Stewart
When you were doing that, I kept thinking about it the whole time. Beck, you take on a fresh take on the Emperor's New Clothes, and you play the emperor. What's one piece of the story that's really fun for you?
Beck Bennett
You know, the. It's. There's such a. Without fully giving it away. There's a real turn. There's like a real setup one way. And then I get to full. Like, I get to make the audience think I'm going a direction, and then I switch directions and, like, build it. Like being emotionally invested in that. How genuine I am about how I've changed. And then. And then making that turn after that is really fun. So I get to really talk from the heart a little bit, and then I get to kind of be kind of gross.
Alison Stewart
Yeah.
Cecily Strong
Simon's got Very good with those turns. It's like gross and sweet.
Beck Bennett
It's a really, really good buildup.
Cecily Strong
Yes.
Alison Stewart
How do you find that balance between gross and sweet? Simon?
Simon Rich
I've always been attracted to, like, unusual juxtapositions, I think. Like, yeah, there's some. There's a lot of weird characters in the show, as you, as you would expect. There's superheroes, there's monkeys, there's time travelers, there's talking horses. But I think at the end of the day, they're weirdly, very emotionally grounded autobiographical stories for me and hopefully for the performers as well. We talked about snl. A lot of these stories I wrote either while I was writing for SNL or sort of about my experiences at SNL trying to make it at that show. And so, yeah, I hope that people will find the show funny, of course, but. But also, you know, emotionally honest and that they'll relate to it, you know, to these characters, as weird as they are, as much as I do.
Beck Bennett
Yeah, I got it. Just to answer your question a little bit from earlier, like it. One of the things I love about the show, as far as I think about ambition and everything, I didn't know what the stories were going to be, but, like, getting into it, it's so relatable how when you try to achieve something in life, even if you achieve what you're going for, there's still a way to be disappointed and feel like you haven't made it. Like, you know, you look at people and you're like, wow, look how incredible they are. But they probably are dealing with the same thing we're all dealing with and being disappointed and frustrated and looking at other people, how other people are a step ahead of them, even though they've accomplished so much. And he does that in such a relatable way through these stories.
Alison Stewart
We're talking about the show all out comedy about ambition. My guests are actor Cecily Strong and Beck Bennett, as well as writer Simon Rich. Cecily, how does the audience change the way you perform tonight?
Cecily Strong
Oh, the audience is always, and this is across the board, I think for every show I've ever done, the audience really indicates sort of how the show's gonna go. You know, you kind of see, what are they into if you have to work a little harder for some audiences, some audiences are a little quieter, some give it up right away and it's like a hot, wild show. But also we have this incredible band who has, like, energy like I've never seen. I mean, Gracie Lawrence, I don't.
Alison Stewart
She's so funny.
Cecily Strong
She's like, not a human. I don't know how she does it.
Beck Bennett
She said she's never taken singing lessons.
Cecily Strong
Which I'm just like, did I have that kind of energy in my 20s? I don't know. I'm very far from it now. But they're incredible. And I'm sort of like, they do 90% of the work to get everybody there, and then we just are lucky enough that we get to show up and then read Simon's very funny words.
Alison Stewart
Yeah. How did Lawrence get involved? Simon?
Simon Rich
So I was a fan of Lawrence, but I'd only met them a couple of times, and Alex suggested that maybe some of their tracks could thematically link to the stories. And boy, was he right. Because. Yeah, I mean, a lot of people have asked me if they composed these songs specifically for the show, and they didn't. They didn't change a word. But I think being New Yorkers themselves, being in this extremely tough, competitive field of professional music making, I think that they were grappling with the same kind of themes that I was in my 20s. And they've written this cluster of songs which are front and center in the show, that are about all the themes that the stories are about, you know, fear of failure, insecurity, jealousy, bitterness, and just trying to. Trying to survive in this sort of make it or break it landscape. And also, in addition to. To performing these songs, they also do. They also live score all the stories and do live sound effects. So it's sort of like watching, like, a. Like going to Thirty Rock in 1949 and seeing a radio show. You know, you get to see them do the live Foley work and do the. Do the horse clops and all the rest. And that's. That's a really fun, dynamic part of the show, too.
Alison Stewart
Oh, there's so much fun. We've had them perform live here.
Beck Bennett
Oh, yeah.
Alison Stewart
Such a good time. When you're on stage, especially when Jim Gaffigan's on stage, there's a little bit of breaking that goes on.
Cecily Strong
A little bit, yeah. Sometimes. Don't tell Simon. Simon, that's not true.
Alison Stewart
Simon. That's not true. But it happens. Do you go with it if you find yourself breaking?
Cecily Strong
Of course. I mean, I think part of the fun and part of the show is that you're coming to see a comedian that you like and you want to see them as well. And so in those moments, you are seeing Cecily laughing at Jim Gaffigan. Yeah. Like, there's been funny things. There's, like In Clabo, I won't give. I won't give too much away, but Jim does play a half man, half ape superhero. And that he does. He's so much physicality in that. That changes every night. And it's always like, okay, I'm gonna. I watch as an audience member on stage, like, what is Jim gonna do tonight with this?
Alison Stewart
What do you do when you break?
Beck Bennett
What do I do when I break? You know, I guess laugh, go for it. I guess I'm laughing when I break. But yeah, it's. I try, you know, I try to just be comfortable with whatever is happening. So, like, yeah, just. Just to go with it and not to be too distracting if I do break.
Alison Stewart
Yeah, I know you have to go because you have to go to rehearsal, but I did want to ask you about your new podcast. Oh, yeah, what's our podcast? Brand new. You're in a studio, you're around audio professionals.
Beck Bennett
Absolutely. Yeah.
Alison Stewart
Tell us a little bit about it.
Cecily Strong
This was your first radio interview?
Beck Bennett
This is my first radio interview. But I do have a podcast.
Cecily Strong
Right, right, but. But the podcast, you understand this room?
Beck Bennett
Oh, well, I mean, it's not. It's a little bit like this. We don't have the glass wall with the other people in there. You know, that's.
Cecily Strong
But like, it was my two way mirror though, right?
Beck Bennett
Yeah, of course. Yeah. But it's. The podcast is called what's our Podcast? It's with me and Kyle Mooney. The idea for the show is that we don't know what our podcast should be about. So we have guests come in each week and tell us what they think our podcast should be about. And then we go into another studio next door and try that podcast with them. So it's kind of like, it's very loose. It's like, it's good, it's funny. Oh, thank you so much. We've. We've had a great time and we kind of approached the show at the beginning with like, what are we doing? We don't know how to do this. So it was very sort of meta examining all the things as we went. But now we've kind of gotten into a groove and it's kind of figured itself out, but it still is under that idea of like, we don't know what we're doing. Maybe you could tell us. And it creates, it just creates this, like, sort of throws a wrench into the interview, you know, when we kind of like go a different direction and it's just, it's really fun.
Alison Stewart
And you were working on something else to do this show. What are you going back to?
Cecily Strong
Yes, well, I'm doing. I'm working on an Amazon show that's in the boys universe, which is very new and fun for me.
Beck Bennett
Love that universe.
Cecily Strong
That's been a fun thing that I lucked into.
Alison Stewart
And Simon, what's next for you?
Simon Rich
It's a lot of screenplays, but they don't let the screenwriters talk about them.
Beck Bennett
Well, Simon, we could talk. Me and Cecily could talk to you about it afterwards.
Simon Rich
Okay, great.
Beck Bennett
Yeah, I'll reach out right afterwards. Perfect.
Simon Rich
Fantastic. Perfect.
Alison Stewart
We've been talking about all out comedy, about ambition. My guests have been Cecily Strong and Beck Bennett as well as Simon Rich. Thanks for making the time today.
Cecily Strong
Thank you.
Beck Bennett
Thanks for having us.
Alison Stewart
Get to rehearsal.
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Date: January 9, 2026
This lively episode of All Of It centers on the new Broadway show All Out: Comedy About Ambition, featuring SNL alumni Cecily Strong and Beck Bennett alongside writer Simon Rich. Hosted by Alison Stewart, the conversation dives into the nature of ambition, the experience of bringing sketch-driven comedy to the Broadway stage, and how performing live for diverse New York audiences shapes the work. The episode weaves together topics of creative process, performer chemistry, and the unique energy of New York’s live theater scene.
Notable Quote:
"It's just something I've always been gravitated to, characters who are very ambitious but don't quite pull it off."
—Simon Rich, 02:19
Notable Quote:
"It's kind of like SNL on Broadway a little bit. It has music. It has these short stories which are like sketches... It's so fun to be like—it's kind of like a musical in that sense."
—Beck Bennett, 03:05
Notable Moments:
Notable Quote:
"It's been different every night. It's very exciting. It's what live theater is supposed to be."
—Cecily Strong, 07:44
Notable Quote:
"At the end of the day, they're weirdly, very emotionally grounded autobiographical stories for me."
—Simon Rich, 12:26
Notable Quotes:
"It's just everybody can see themselves in it...all of us, especially living in New York, I do think you have to be ambitious. And it's all about, like, what do you put up with in order to be in New York?"
—Cecily Strong, 09:57
"When you try to achieve something in life, even if you achieve what you're going for, there's still a way to be disappointed and feel like you haven't made it... he does that in such a relatable way through these stories."
—Beck Bennett, 13:18
Notable Quotes:
"They do 90% of the work to get everybody there, and then we just are lucky enough that we get to show up and then read Simon's very funny words."
—Cecily Strong, 14:44
"It's sort of like watching, like, going to Thirty Rock in 1949 and seeing a radio show."
—Simon Rich, 16:06
Notable Moment:
Cecily describes watching Jim Gaffigan play a half-man, half-ape superhero and the unpredictable fun that brings on stage (16:34–17:23).
Simon Rich, on ambition:
"None of these characters really do make it, but they certainly try, for better and for worse." (09:31)
Cecily Strong, on performing New York:
"You got New York right. And not many people do. And you guys, you got it right." (10:54)
Beck Bennett, on SNL vs. Broadway:
"The experience is like snl, but it's so much more decent and just more relaxed and just enjoy." (08:26)
Simon Rich, on emotional resonance:
"I hope that people will find the show funny, of course, but also, you know, emotionally honest and that they'll relate to it." (12:26)
Cecily Strong, on the band's role:
"They do 90% of the work to get everybody there, and then we just are lucky enough that we get to show up and then read Simon's very funny words." (14:44)
The tone is warm, playful, self-deprecating, and thoughtful throughout—mirroring the spirit of both New York theater and the "All Out" production. The guests bounce jokes, reminisce about SNL, and dig into deeper questions about creativity and ambition, always returning to the ways in which community, effort, and vulnerability make live performance special.
This episode offers an engaging look at how live comedy and musical theater collide in All Out, shedding light on the creativity and camaraderie behind the curtain. Listeners will come away with a sense of the vibrant, ever-shifting spirit of New York's theater scene, the joys and anxieties of ambition, and the thrill of making—then remaking—a show night after night.