207. Chris Fleming Returns: He Is Way More Popular This Time

Mon Mar 30 2026

The last time comedian Chris Fleming was on Working it Out, the episode was titled “He Should Be Way More Popular.” In the 2 years since then Mike’s wish has come true. Chris and Mike chat about the pros and cons of having a higher profile in comedy, including the protective steps needed to avoid legal action from Adam Driver over a bit. Mike also takes the chance to respond to the shots Chris takes at Mike in his new HBO special Live at the Palace, and Chris talks about getting glared at by Ryan Gosling. Plus, Mike and Chris work out lots of new jokes about drum circle friend groups, hotel smells, and dog DNA tests.

Transcript

Chris Fleming (0:00)

I went out on stage opening for somebody, and it was silent except for one guy who just said, let's go, Weird Al.

Mike Birbiglia (0:07)

Oh, my God. Let's go. Let's go, Weird Al.

Chris Fleming (0:10)

And then it's like, why am I. Why am I even bothering?

Mike Birbiglia (0:15)

Why is that heckle so good?

Chris Fleming (0:17)

It's so.

Mike Birbiglia (0:18)

Let's go weird out.

Chris Fleming (0:19)

Let's go weird out.

Mike Birbiglia (0:23)

That is the voice of the great Chris Fleming. Let's go, Weird Al. Chris Fleming is one of my favorite comics. He is on fire. He was on. He was on this podcast a year or two ago. He makes me laugh so hard. He has a new special out on HBO called Live at the Palace. You know that I really, truly love this special because I recommend it in addition to on this podcast to everyone I know. It is just silly and ridiculous. And he is silly and ridiculous and very talented. It's no fluke how silly and ridiculous he is. He's worked at it and we talk about that today. We have a really good chat. By the way, he also has a special that's really funny on Peacock, streaming on Peacock called Hell. I want to mention something fun, by the way, the audio of my show, the Old man in the Pool is now on Spotify. That was like a whole thing. I know. It wouldn't seem like that would be a whole thing. You're probably thinking, of course it is. Nope, it's a whole thing. So now on a Spotify, you can listen to the Old man in the Pool. Thank God for Jokes. My Girlfriend's Boyfriend, My Secret Public Journal Live and to Drink. Mike, if you want to reference all of the jokes that Jack Antonoff references over and over again when he comes on this podcast. Hopefully he's coming on again soon because there's a new Bleachers album coming out. So bug him online about that. By the way, thanks to everyone who signed up for Working It Out Premium on Apple Podcasts. We love our little familia over on Premium. On Apple Podcasts, what you do is you go to the podcast app Apple Podcasts and then you click on Mike Birbigli is Working It Out. There's a thing underneath where it says latest episode, where it says working out premium 4.99amonth. And if you subscribe, what happens is you get these bonus episodes, which we think are really funny and interesting and actually even more behind the scenes than the show itself is. And every other episode, like there's 200 and something episodes of the podcast, you get no ads. So we think it's a great Deal. You support the show. We're an independent production. We really appreciate it. And you get these bonus episodes. One of them is where I work out new jokes entirely. I share audio from my comedy seller set recently. Like an all new story. There's one with Pete Holmes where we work out listeners jokes. Anyway, I think they're really good and we're making more and more. Also, I will officially be in Los Angeles at the Netflix Is a joke festival May 6 at the Wilshire E Bowl. Mike Birbiglia working it out with friends. I already know who one of the friends is and it's really cool comedian who's been on this podcast before, so it's gonna be great. Hope to see you there then. Oh, actually in the month of May, I will be supporting John Mulaney on tour along with Fred Armisen in Colorado Springs, Eugene, Oregon and Bend, Oregon. Oh, I'm excited about those. Also August 23rd in Moorhead, Minnesota, a bunch of dates with John Mulaney. Really excited about those. Those shows are awesome. His touring set right now is, I think, as I said it on this podcast with him, I think it's as funny or funnier than anything he's ever done. So go get tickets to that all@birdbigs.com thanks to everyone who signed up for the text message alerts. If you're on the mailing list and you want to make sure you get alerts about shows in your area, text BURBIGS to 917-444-7150 to be the first to know about my upcoming shows and tours. This is a great one with Chris Fleming. He roast me in his new special. So I roasted him back. I got my chance to roast him back. Like I said, um, he's had a big run in the last couple years and we talk about the perils that come with that. Artistically, we both work out new jokes. I was really pleasantly surprised he came with some new jokes. We also break news about Chris Fleming playing a role in the new Judd Apatow film. And I do too, apparently. It's a great one. Join my conversation with the great Chris Fleming. Working it. This is a great one. At one point in this special, you refer to Terry Gross as Theresa Disgusting. Like, where did that come from? And have you heard from Ms. Gross?

Summary

Podcast Summary

Podcast: Mike Birbiglia's Working It Out
Episode: #207 – Chris Fleming Returns: He Is Way More Popular This Time
Date: March 30, 2026
Guests: Mike Birbiglia (host), Chris Fleming (guest)
Main Theme/Purpose:
A lively, candid conversation between Mike Birbiglia and comedian Chris Fleming, focusing on Chris’s recent surge in popularity, the perils and joys of comedic success, behind-the-scenes stories from both their careers, the art and mechanics of standup, and working through new, untested material—plus some loving mutual roasting.

Episode Overview

This episode marks Chris Fleming’s return to "Working It Out." Since his previous appearance, Fleming’s star has risen sharply, especially following his acclaimed HBO special "Live at the Palace." The comedians discuss fame, the creative process, challenges of growing an audience, working out new jokes, and maintaining authenticity in comedy. The conversation is infused with playful roasts, insights into writing and performing standup, touching on handling pressure, and staying grounded as success grows.

Key Discussion Points & Insights

1. The Joy and Terror of Recognition

Topic: Chris Fleming’s newfound popularity and its impact

Fleming reflects on how his audience has changed—from mostly art therapists to now getting more male fans ("more men yell 'Chris!' at me on the street"), noting both amusement and a sense of being startled by it.
Birbiglia points out how quickly Chris went from being labeled “underrated” to headlining major venues.

Notable Quote:
"[Now] it just means I’m gonna have to play Jake Shane’s grandma in something in a Euphoria reboot about elder abuse. That’s all it means." – Chris Fleming (15:00)

2. The Mechanics and Philosophy of Comedy

Topic: How bits and standup are constructed and the emotional risks

The two analyze why some bits succeed famously while others bomb, even with the same material.
Fleming references his method—rarely mapping out a full hour, preferring a “spilling out” approach, and comparing set-crafting to sleepover giggles and hypnosis.
Both stress the importance of clarity ("let them in and be really clear") and the audience's desire for something unexpected.

Notable Quote:
"Sometimes the best analogy is just a very… Like Tom Waits will do something so highfalutin and then talk about, like, you know, like a hammer." – Chris Fleming (51:28)

Timestamps:

[19:28] Birbiglia admires how Chris’s special, despite not being narrative, keeps audiences hooked.
[24:00] Discussing “freshness” in live performance—the vital energy of first-time joke delivery.

3. The Perils of Press and Mechanization of Success

Topic: Downsides of achieving mainstream recognition

Fleming misses the days of “scheming in the shadows” where art is made without pressure.
He describes press obligations as feeling like being "mechanized," which can make it hard to find creative quiet.

Notable Quote:
"When you feel like you are being mechanized, how do you ever… when am I going to be able to go back under my rock and do the thing that gets me the thing you guys are all liking?" – Chris Fleming (17:10)

Timestamps:

[16:51] Chris on the worst part of success: "The press. You can scheme in the shadows, that’s where the art happens."

4. Support, Roasts, & Mutual Influences

Topic: Comedians roasting each other and their creative community

Chris lovingly skewers Birbiglia in his special, and Mike fires back with a series of “light burns.”
Roasting is discussed as distinct from harsh comedy roasts—more akin to “light marshmallow toasting.”
Deep mutual respect surfaces (“I talk about you in every special,” Fleming admits to Birbiglia.)

Notable Roasts:

“Chris Fleming is like if Big Bird went to Wesleyan.” – Birbiglia (08:35)
“Chris Fleming. Or as I like to call him, gender-fluid Dane Cook.” – Birbiglia (08:50)

5. Handling Bombs and the Comedy Rollercoaster

Topic: Recent and past failures

Both recount “bombing” in front of difficult crowds (Birbiglia at the Ally Coalition, Fleming at a Grammys party with Lorde in attendance).
They emphasize that bombing is unavoidable, and sometimes connects you to the rawness of performing.

Notable Quote:
"I had to bomb in front of Lorde recently… I was like, Lorde, do not watch this. And she was sidestage…" – Chris Fleming (13:57)

6. The Alchemy of Audience and Material

Topic: Why material is sometimes “alive,” and sometimes not

Both reflect on how jokes can kill one night and die the next, regardless of content.
They talk about filming first versions of bits for spontaneity (“first time I’m doing a bit and put it out”).
The chemistry with an audience is unpredictable, akin to “animal” sensing.

Timestamps:

[24:43] The unpredictability of audience reaction and why freshness can’t be replicated.

7. Practical Comedy Wisdom & Advice

Topic: Mentor advice and the value of clarity

Fleming’s mentor Rick Jenkins advises: “You can get as crazy as you want… but if they don’t know what you’re talking about, let them in and be really clear.”
Birbiglia recalls similar advice: “You’re not conveying the thing that’s in your head… you just need to explain it better.”

Notable Quote:
"People are willing to go with you, even if it’s weird, which is a term I resent." – Chris Fleming (45:29)

Timestamps:

[43:56] On the importance of letting the audience in and being clear even with the weirdest material.

8. Working Out Untested Material

Topic: Live workshopping of new jokes

Both share notebook bits in-progress, giving each other feedback.
Fleming works through a bit about friends going from drum-circles to “espresso martini” brides.
Birbiglia tests a joke about acquiring a hotel-room smell, and another about horrifyingly dull swim meets.
They discuss the difficulty of setting up complicated contemporary references for an audience.

Notable Quotes:
"[You] used to free bleed on your enemies' couches, and now you’re little Miss Espresso Martini walking down the aisle…" – Chris Fleming (47:56)
"…I wake up in the morning and the smell is gone. And then I realized the smell isn’t gone. I just am the smell now." – Mike Birbiglia (49:47)

9. The Value of Small Rooms and Local Comedy Scenes

Topic: Growth in smaller, more intimate venues

Both encourage seeking out and performing in small, local comedy spaces.
Emphasize real growth and creativity often happen there, before the expectations of big venues.

Notable Quotes:
"All good things start in little rooms." – Chris Fleming (31:44)

Memorable Moments & Notable Quotes

On Terry Gross as “Theresa Disgusting”
"I saw a photo of her accepting an award at iHeartRadio… She’s dressed like Mad Max… steampunk goggles, Falconer's glove. She’s badass." – Fleming (05:36)
On the anxiety of headlining:
"You can very quickly dip into overrated… There’s something cozy about being considered underrated." – Fleming (33:44)
On comic narrative:
"It really is like a sleepover… There does feel… almost every show feels giddy sleepover energy." – Fleming (23:00)

Selected Timestamps for Key Segments

00:00 – 00:18: Cold open—Chris’s heckler (“Let’s go, Weird Al”)
05:17 – 08:10: Terry Gross anecdote; mutual roasts begin
13:49 – 14:35: Bombing at star-studded events (Lorde at Grammys party)
16:51 – 17:26: Fleming on the downsides of mainstream success and missing creative quiet
19:28 – 22:49: Birbiglia and Fleming dissect how non-narrative comedy keeps audiences invested
24:00 – 26:19: The “freshness” and ephemeral magic of live performance
31:22 – 34:00: The primacy of small rooms for creative growth
47:16 – 49:40: Working out new jokes (drum circle friends, “espresso martini” bit, hotel room smell)
53:13 – 54:17: Hazards of being a vegetarian comic, “Food Inc. wears off after six years"
56:05 – 56:24: New idea—“the legendary 1970s chihuahua” in LA canine DNA
60:18 – 61:00: Charity selection—Planned Parenthood

Additional Noteworthy Sections

Chris Fleming’s Approach to Comedy

Works best when communicating with audiences as if they were friends at a "middle-school sleepover."
Values disarmingly honest, clear communication and being willing to bomb in service of new material.

Handling Fame and Remaining Authentic

Fleming is “thrilled” by wider popularity but guarded about losing the privacy and “scheming in the shadows” that fostered his art.
Acknowledges more “random numbers” reaching out (old acquaintances resurfacing).

Owning the “Weird” Label

Discusses discomfort with being pigeonholed as “weird,” and how mainstream press sometimes mischaracterizes his persona.

Closing Thoughts

Mike and Chris’s dynamic is equal parts camaraderie, affectionate ribbing, and genuine creative exchange. The episode is a testament to comedy’s focus on connection—both with the audience and within the comedy community. Chris celebrates his hard-earned success with humility, holding onto the process that underpins his work rather than chasing new trends. Both comics underscore the essential, ongoing vulnerability of standup: "letting it spill out," doubling down, and returning to the joy of the small room, even after hitting the big time.

Charity Highlight

Working It Out for a Cause:

Chris Fleming chooses Planned Parenthood as his nonprofit.
Mike Birbiglia commits to contributing and linking to them in the show notes.
(60:18–60:54)