Mike Birbiglia's Working It Out: Advice for New-ish Comedians (with Gary Simons and Listener Questions) Release Date: May 19, 2025

In this engaging episode of Mike Birbiglia's Working It Out, host Mike Birbiglia welcomes comedian Gary Simons for a return visit. Building on their shared experiences touring together during Gary's early stand-up career, the duo delves deep into the journey of emerging comedians, addressing challenges, sharing insights, and answering listener questions.

Guest Spotlight: Gary Simons

Mike kicks off the episode by reintroducing Gary Simons, highlighting their two-year touring partnership leading up to Gary's performance in Mike's special, The Good Life. Gary’s ascent in the comedy scene is notable; after joining Mike on tour, he successfully broke into the Comedy Cellar in the fall and has been thriving since October.

[00:10] Mike Birbiglia: "If you are someone who is in the first few years of doing standup or just trying a new kind of creative form, this is a great episode."

Evolution in Stand-Up: From Newcomers to Veterans

Gary reflects on his growth over the past few years, emphasizing the importance of stage time in honing his craft. He contrasts his current capacity to attend open mics with the earlier days when he found it nearly impossible to attend as many as 50 a week—a routine suggested by established comedians like Chris DiStefano.

[03:36] Gary Simons: "Last time I was on the podcast, we talked about how, like, the important thing with, like, stand up is just getting as much stage time as possible, which I feel like is true."

Mike shares his own early experiences in Washington, D.C., where open mics were sparse, leading him to perform non-comedic acts like music at available venues. Upon relocating to New York, the abundance of open mics and varied performance opportunities significantly boosted his exposure and performance frequency.

Navigating Tough Mics and Building Resilience

A significant portion of the conversation revolves around handling challenging performances and embracing the bombing experience as a stepping stone to improvement. Gary recounts a particularly tough mic in Connecticut where the audience was unaware they were attending a comedy set, leading to unexpected heckling and a loss of confidence.

[05:40] Gary Simons: "Can you stay up there? Can you keep trying to. Can you win them over eventually?"

Mike shares a similar anecdote from Springfield, Missouri, where despite a poor performance, the presence of a talented young comic in the audience provided an unexpected boost.

[07:02] Gary Simons: "They didn't know you weren't supposed to heckle. They just heckled because they're like, you're talking over my game."

Both comedians agree that such experiences, while initially disheartening, ultimately strengthen their ability to perform under adverse conditions and refine their approach for future shows.

Balancing Old and New Material

The duo discusses the delicate balance between refining existing material and introducing new bits. Mike introduces his theory of "open strong, close strong," suggesting that comedians should secure their best material at the beginning and end of their sets, using the middle to experiment with new content.

[12:08] Mike Birbiglia: "Open strong, close strong. And then, yeah, use the middle to try out."

Gary echoes this sentiment, emphasizing the importance of having a solid foundation while allowing space for creative exploration.

Authenticity vs. Club-Comedy Pressure

A listener question prompts a discussion on maintaining personal authenticity amidst the rhythmic demands of club settings. Mike recounts his initial fear of adopting a "hacky" style influenced by club environments, a concern alleviated by advice from Mitch Hedberg.

[09:39] Gary Simons: "Do you feel like there is any changes that like you did make even though he told you that?"

Mike admits to evolving his style over the years, shifting from the fast-paced, louder delivery suggested by Jeff Ross to a more conversational and personal approach.

[10:27] Mike Birbiglia: "More personal one on one feeling. And by the way, it's not bad advice for being a club act."

Overcoming Stage Fright and Self-Doubt

The episode features heartfelt advice for newcomers grappling with self-belief and stage anxiety. Listener Erica poses a question about overcoming societal conditioning that women often face in taking up space on stage.

[17:05] Erica: "As a woman, I...have been conditioned to not take up space...how can I get over that and really start to believe that any given story that I want to tell is actually worth telling."

Both Mike and Gary empathize, sharing their own insecurities and emphasizing the universality of these feelings among comedians. Mike encourages embracing the storytelling aspect of comedy, moving beyond seeking immediate laughs to conveying genuine experiences.

[21:14] Mike Birbiglia: "Tell the story you feel like no one's telling. And I think the more specific that gets and the more it's what you're feeling, potentially the funnier it'll be."

Crafting Relatable Yet Complex Characters

Addressing a question about telling stories where the comedian is perceived as unlikable, Mike and Gary discuss the balance between maintaining relatability and managing audience perceptions. They highlight the importance of acknowledging the complexity of situations and the comedian's intentions within their narratives.

[22:32] Listener: "How do you tell a story that makes you seem completely unlikable while still keeping the audience on your side?"

Gary shares his approach of embedding jokes that humanize him, ensuring the audience remains sympathetic despite morally ambiguous actions.

Practical Tips for Aspiring Comedians

Throughout the episode, Mike and Gary offer actionable advice for those new to stand-up:

• Mantras for Confidence: Both share personal rituals to boost confidence before performances. Gary utilizes a Wonder Woman pose combined with affirmations to center himself, while Mike employs a grounding-and-inspiration gesture.

  [27:51] Gary Simons: "I tell myself, like, affirmations, like Wonder Woman. Why is it one? Why not Wonder Woman?"

  [27:51] Mike Birbiglia: "Tell stories from the earth. Inspiration from the heavens."

• Experimentation in Open Mics: Emphasizing that open mics are exploratory spaces where everyone is refining their act, Mike encourages viewing performances as collective learning experiences rather than competitions.

  [30:49] Mike Birbiglia: "If this is helpful, for anyone who's going to open mics, it's like everyone's just trying to figure it out."

• Avoiding Perfectionism: They advise against over-rehearsing or memorizing material to the detriment of natural delivery, suggesting instead focusing on conveying ideas and emotions authentically.

  [34:48] Mike Birbiglia: "To not memorize the monologue as much as you're memorizing just bullet points."

Conclusion: Embracing the Journey

The episode concludes with Mike and Gary reflecting on their shared experiences and the ongoing process of "working it out" in comedy. They reinforce the idea that authenticity, resilience, and continuous experimentation are key to growth in the stand-up arena.

[43:40] Mike Birbiglia: "Keep finding your point of view. Keep finding your specific take on the... break out the parts that you might have a take on, and then know that if you can come up with a funny take on that, you can include it in the story."

Gary expresses his excitement for future projects, highlighting the collaborative spirit of the podcast.

[44:05] Mike Birbiglia: "There's no... We don't have to stop making jokes, though these versions might joke they'll someday breathe clearer."

Key Takeaways:

• Stage Time is Crucial: Regular performances, even in challenging environments, are essential for growth.
• Embrace Failure: Bombing is not only inevitable but also a valuable learning tool.
• Balance Material: Maintaining strong, reliable content while experimenting with new material fosters both stability and creativity.
• Authenticity Matters: Staying true to one's unique voice prevents falling into generic club-comedy traps.
• Community Support: Building relationships with fellow comedians provides encouragement and constructive feedback.

This episode is a treasure trove for aspiring comedians, offering a blend of personal anecdotes, practical advice, and empathetic discussions that illuminate the nuanced path of stand-up comedy.