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
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Anna Gasteyer: "Imposter syndrome is everything everywhere all the time. How do we teach people not to have that?" [26:10]
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Anna Gasteyer: "The stage fog is a real challenge. It cuts your voice in half and gets in the way of everything." [53:35]
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Anna Gasteyer: "Finding the connection through Elphaba's sense of humor was key." [55:35]
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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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