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169. Ira Glass Returns: This American Comedian

Mike Birbiglia's Working It Out

Published: Mon May 05 2025

Ira Glass has appeared on the Working It Out podcast three times before, and usually it’s Mike asking Ira for advice, whether it’s about podcasting or storytelling. But now the tables have turned: Ira recently listened to a stand-up set he performed years ago, he has the itch to try it again, so he’s come to Mike for comedy advice. On this episode, Mike and Ira listen to Ira’s old stand-up set in real time, break down what worked and what didn’t, and brainstorm ideas for Ira’s next set. Please consider donating to your local public radio or television station.

Summary

Summary of Episode 169: "Ira Glass Returns: This American Comedian"

Podcast Information:

  • Title: Mike Birbiglia's Working It Out
  • Host: Mike Birbiglia
  • Episode: 169. Ira Glass Returns: This American Comedian
  • Release Date: May 5, 2025

Introduction: A Special Collaboration

In this milestone episode, Mike Birbiglia welcomes Ira Glass, the celebrated host of This American Life, for a unique and collaborative session. Unlike previous episodes where Mike sought Ira’s wisdom, this time the roles reverse as Ira seeks Mike’s expertise to refine his newfound interest in stand-up comedy.

Mike Birbiglia [00:10]:
"Before he was episode number one, he was episode number 100. And usually it's me asking Ira for advice. He's given me so much brilliant advice over the years, and now the tables have turned."

Ira’s Stand-Up Journey Begins

Ira Glass shares his inspiration to venture into stand-up comedy after revisiting his performances from a decade ago. Encouraged by Mike, Ira decides to bring his old stand-up material to the podcast for constructive critique and enhancement.

Ira Glass [02:20]:
"I don't know if I really wanted to actually make a stand-up set and put myself into the position that, like, you're in of I have nothing. So where do I begin?"

Analyzing Ira’s Stand-Up Material

The core of the episode revolves around dissecting Ira's stand-up routine. Mike and Ira listen to excerpts from Ira's past performance at the Eugene Mirman Festival, identifying strengths and areas for improvement.

Ira Glass [05:18]:
"This is a comedy show."

Unknown Speaker [05:20]:
"I brought along, like, music just in case, like, I would start to feel like, oh, is this going on?"

Mike critiques Ira’s approach to joke delivery, particularly his use of strong language and how it impacts audience perception.

Mike Birbiglia [09:00]:
"Because everyone sucks for everything. Every location, every whatever."

Ira Glass [09:25]:
"They do not advertise hiking properly at all. So is that why?"

Developing Jokes Through Storytelling

The discussion shifts to the mechanics of joke construction, emphasizing the importance of relatable setups and surprising punchlines. Mike illustrates this with examples from his own work, encouraging Ira to leverage personal stories.

Mike Birbiglia [15:30]:
"I think a lot of it is you have a setup, something that we all believe to be relatively true, and then the thing takes a left turn so that we have a surprise or something we don't expect."

They explore Ira's story about admitting he’s never been hiking, examining how to expand this premise into a compelling stand-up bit.

Ira Glass [14:32]:
"What did they say? And then somebody, like, near me is like, sex while hiking."

Navigating Sensitive Topics with Humor

Ira expresses his desire to incorporate personal and sensitive subjects, such as his father's dementia, into his comedy. Mike provides guidance on balancing vulnerability with humor, sharing his experiences of writing about serious topics.

Ira Glass [37:10]:
"I don't like the idea of her having to take care of me if I have dementia."

Mike Birbiglia [40:05]:
"I think confessions are part and parcel of stand-up. If you're not telling secrets on stage, who cares?"

They discuss the challenge of finding humor in deeply personal narratives and the importance of authentic storytelling in comedy.

Practical Advice for Aspiring Comedians

Mike outlines a step-by-step approach for developing stand-up material:

  1. Write Setups: Identify universally relatable truths.
  2. Craft Punchlines: Develop multiple humorous responses or twists.
  3. Trial and Error: Test jokes in front of live audiences and refine based on feedback.

Mike Birbiglia [31:26]:
"Write out a setup, something we all believe to be true. And then write out five punchlines."

He shares anecdotes from his early days at the DC Improv, emphasizing the importance of persistence and resilience in comedy.

Enhancing Joke Structure and Flow

The conversation delves deeper into maintaining a cohesive narrative within a stand-up set. Mike advises Ira on linking jokes seamlessly, ensuring each punchline propels the story forward rather than feeling disjointed.

Mike Birbiglia [26:32]:
"Once you have the subway analogy, which is a good analogy, but then you're just kind of like going like. You're kind of just like free associating."

They brainstorm ways to transition between topics, such as comparing hiking to walking in a city, to create a more engaging and structured routine.

Embracing Vulnerability and Personal Stories

Ira contemplates how to incorporate his familial experiences into his comedy without losing the humorous essence. Mike encourages embracing these personal narratives, suggesting that authenticity resonates with audiences.

Ira Glass [43:28]:
"But like, other things where slowly we realize we're the out. We're the ones who are on the outside of the thing."

Mike Birbiglia [40:55]:
"If you're not telling secrets on stage, who cares?"

Conclusion: A Path Forward for Ira

As the episode wraps up, Mike praises Ira’s willingness to explore new creative avenues and suggests future collaborations. They also highlight the importance of supporting public broadcasting, aligning with Ira’s professional roots.

Mike Birbiglia [53:40]:
"I'm open to you coming back."

Ira Glass [53:54]:
"I think I was, too. So should I come back with the... material?"

Notable Quotes

  • Mike Birbiglia [15:30]:
    "I think a lot of it is you have a setup, something that we all believe to be relatively true, and then the thing takes a left turn so that we have a surprise or something we don't expect."

  • Ira Glass [37:10]:
    "I don't like the idea of her having to take care of me if I have dementia."

  • Mike Birbiglia [31:26]:
    "Write out a setup, something we all believe to be true. And then write out five punchlines."

  • Mike Birbiglia [40:55]:
    "If you're not telling secrets on stage, who cares?"

Supporting Public Broadcasting

In a heartfelt conclusion, Ira advocates for supporting public radio amidst current challenges, urging listeners to donate to their local stations.

Ira Glass [53:04]:
"Given the current challenges facing public broadcasting, if people listen to their local public radio station, this would be a really good time to donate."

Mike Birbiglia [53:16]:
"I'm gonna give you WNYC, because that's our local one."

This episode serves as an insightful exploration of the intersection between storytelling and stand-up comedy. Through constructive feedback and collaborative brainstorming, Mike Birbiglia and Ira Glass demonstrate the nuanced process of transforming personal narratives into engaging comedic material. Listeners gain valuable perspectives on joke crafting, the importance of vulnerability, and the relentless pursuit of comedic authenticity.

No transcript available.