194. Pete Holmes Returns: Vulnerability is Everything

Mon Dec 01 2025

This week, Pete Holmes returns to the studio for one of Working It Out’s most joke-dense episodes ever. Mike and Pete work out jokes about strangers in hot tubs, why Jerry Seinfeld sounds like his own name, and how cool guys in movies swallow their pills without water. Plus, the comedy advice Pete wishes he knew when he was starting out. Want more of Mike and Pete? Subscribe to Working It Out’s premium feed on Apple Podcasts to listen to their bonus episode together where they work out listener-submitted material!

Transcript

Mike Birbiglia (0:00)

Have you noticed all comedians are like their name?

Pete Holmes (0:05)

Oh, that's great.

Mike Birbiglia (0:06)

Bill Burr is. Bill Burr.

Pete Holmes (0:08)

Yeah, Bill.

Mike Birbiglia (0:09)

Bill Burr. Stephen Wright. Jerry Seinfeld. Seinfeld. Ray Romano. Romano. And then someone yelled out Birbiglia. And I went, mike Birbaglia. Birbiglia is like the sound a water cooler jug makes. That's you. It kind of needs to be changed.

Pete Holmes (0:42)

That is the voice of the great Pete Holmes. Pete Holmes is back. Come on, Come on, everybody in the studio. We haven't had Pete Holmes in the studio in years. One of my favorite comedians, he has a podcast called you Made It Weird. One of my good friends, he's been on the show many times. As a matter of fact, if you want to go back and listen, almost exactly a year ago, we did our favorite Christmas movies as an episode. I think it's a pretty good list. I actually think if you're looking for a holiday movie, go back and listen to that one. It's a good list. Here's what you need to know about these episodes with me and Pete. It's a little bit like listening to a phone call between me and Pete. Sometimes we burn each other. We're mean to each other, but we love each other. That's the key thing. I really love this chat that we have today. We actually punch up jokes, punch up each other's jokes. I think quite effectively. We break some ground on some jokes that, you know, that were kind of nowhere before the episode. So that's great. It's exactly the premise of the podcast, by the way. Thanks to everyone who came out last week to me and Jenny's jokes and poems at Joe's Pub in New York City. That's a. That's an event that my wife Jenny and I do every few months. We're doing another one soon, if you want to be the first to know, because it's limited, you know, it's 160 seats at Joe's Pub, and so the tickets go really fast. If you want to be the first to know about the next Joe's Pub show, which is probably going to be in January, text Birbigs B I R B I G S on your phone to the number 917444, 7150. And you'll be the first to know when those tickets go on sale. Also, I will be appearing in the Broadway show all out from January 13 through 18 alongside Cecily Strong and Wayne Brady. All Out. I've mentioned this before, but it's a. It's a comedy on Broadway written by a great Simon Rich wrote for snl. He's written many hilarious books. He's written for the New Yorker. And it's actors, like a rotating cast of actors. And Jon Stewart's doing it. I think Jim Gaffigan's doing it. I think Abby Jacobson's doing it. Anyway, it's a great bunch of actors doing it. And then it's all in front of a live band. The band is called Lawrence. It's a band that I really like and they're playing their own original songs. So I'm really excited about it. I think you should see it. I know a lot about you and I. I do think you should see it. You can get tickets@allout broadway.com thanks to everyone who signed out for working it out. Premium on Apple Podcasts Last week we released a bonus episode with Pete Holmes where we punch up listeners jokes. Today we punch up each other's jokes on that episode. Punch up listeners jokes. If you sign up, you support the show, which we really appreciate. And then you get these premium episodes like the one where me and Pete punch up people's jokes and you get no ads like on any episode. And this is part of the reason that I have premium on some podcasts that I listen to. My wife Jenny and I fall asleep to podcasts. We do the setting on Apple podcasts which is like, play next, play next, play next, play next. And we do it with premium subscription. So there's no ads. So there's not like, hey Ra, get this thing. I'm not gonna say a thing. Cause then it'll alienate the sponsors. But you know what I mean. That's actually the reason why we have premium on one of the things. I love this conversation I have with Pete Holmes today. As I said, he's been on the show a lot of times. We razz each other a bit. We go deep into stand up comedy, philosophy and religion and the religiosity of comedy. Love talking to Pete. Enjoy my conversation with the great Pete Holmes.

Summary

Episode Overview

Podcast: Mike Birbiglia’s Working It Out
Episode: 194. Pete Holmes Returns: Vulnerability is Everything
Host: Mike Birbiglia
Guest: Pete Holmes
Date: December 1, 2025
Theme:
A candid, hilarious, and deeply insightful exploration of stand-up comedy, vulnerability, joke-writing, and the often unspoken emotional philosophy of performing. Birbiglia and Holmes “work out” new material, share war stories, challenge each other’s ideas, and delve into why authenticity and sensitivity are at the core of great comedy.

Key Discussion Points & Insights

1. Comedians and Their Names

Opening Bit ([00:00])
- Mike observes that many comedians’ names perfectly fit their comedic persona ("Bill Burr is Bill Burr," "Stephen Wright is Stephen Wright," etc.).
- Pete adds, "Were they born into these names, or did they grow into them?" ([27:25])

2. Philosophy of Stand-Up: Audience Connection & Vulnerability

The duo discusses the myth that it's always the comedian’s job to make things work—sometimes, "it's the audience, too." ([07:19])
Mike stresses, “I’m not doing this at you. I’m doing this with you. It’s different every time because of you.” ([08:17])
Eddie Murphy Doc Reference ([09:04])
Pete recounts Murphy’s emphasis on “sensitivity and vulnerability” being the true key to artistry:

“He really hangs a lantern on that. ...Actually it’s him being like, no, no, no. It’s about sensitivity.” -- Pete ([09:23])

3. Blending New Material and Punching Up Jokes

Both admit the podcast sometimes focuses less on punchline “workshopping” than advertised, and today’s goal is to change that. ([04:51])

4. On Cut Jokes and Comic Voice

Mike discusses jokes that don’t make it because they feel inauthentic—despite their technical quality ([16:14]).

“There’s a level of intuition ...it’s like looking at your whole show as a piece feelings, not just for them, but for you.” — Mike ([15:39])
Story of a joke about his mother:

“When it didn’t work, it was too costly. It made me feel like a bad son. So I just cut it.” — Mike ([18:10])

5. The Dynamics of Joke Context

Both explore how a joke's success often relies on subtle audience setup and perceived justice ("comedy balance").
Mike: “Justice is a big part of comedy...” ([19:35])

6. On Self-Perception & Competitiveness

Pete: “You can’t see yourself. ...Dave [Chappelle] can’t tell how great he is.” ([11:42])
Later, on being a bad athlete:

“I’m a fierce competitor who loses.” — Pete ([47:27])
- Mike reframes:
  
  “You don’t know what a disappointment it is to be fiercely invested in winning, and God made you like this.” — Mike ([47:55])

7. Joke Construction, Authenticity, and the Art of Editing

Holmes and Birbiglia probe the fine line between a “good” joke and the right joke for a particular performer.
Discussions about jokes being cut because they might send the wrong message or don’t fit their personal ethos ([23:15]–[24:20]).

8. Comparing Modern and '80s Parenting

Pete’s bit on modern fathers being more anxious, multi-tasking parents versus the distant "monsters" of Pixar’s past ([36:02]–[38:04]).
Analogies: “We're all iPhones with too many apps.” — Pete ([37:35])
Mike: “In the '80s, it was a landline, and dad didn’t answer it half the time.” ([37:43])

9. Cinematic Coolness: Why Do We Want to Be Movie Stars?

Explores the trope of “cool” in movies—quiet characters, swallowing pills without water ([40:09]), and how these markers of coolness are unattainable for “real” people.
Pete:

“There’s something more there...how are you never going to be the thing you grew up wanting to be?” ([44:03])

10. Storytelling: The “Massage Parlor” Story

Mike shares an extended personal story about an awkward (but platonic) massage parlor experience in Canada ([53:35]–[59:51])—punctuated by physical comedy, and his pride in “being the Elvis Presley of not getting an erection” ([56:34]).
Pete encourages weaving personal vulnerability and cinematic references together across stories for greater callback potential ([59:30]).

11. Vulnerability, Authenticity, and Growth

Repeated theme:

“Vulnerability is everything.”
- Pete notes how Steve Martin, Eddie Murphy, and others succeed not by bravado, but emotional exposure and honesty ([09:04]–[09:39]).

12. Working Out for a Cause

Pete highlights Homeboy Industries, a gang rehabilitation program, as a favorite charity ([64:51]); Mike praises its ethos of “unconditional love.”

Notable Quotes & Moments

On artists' sensitivity:
“There’s a point at which he [Eddie Murphy] says the key thing about artists is their sensitivity and their vulnerability.” — Pete ([09:04])
On failed jokes:
“If you were in the audience, you wouldn’t laugh. ...You haven’t found out how to make yourself laugh yet.” — Mike ([13:43])
On authenticity:
“Just because you thought it doesn’t mean you have to say it. ...Especially if it’s a joke. Yeah, it’s funny.” — Mike ([14:13])
On joke selection:
“There’s jokes that are good jokes...but for whatever reason, out of your mouth, people are like, no.” — Pete ([18:10])
Mike on his all-time most worked-on (discarded) joke:
"Have a God that's better than your manager at Applebee’s. But...could never make that work. ...It’ll be in 'Kill Your Darlings,' for sure. So it'll live." ([21:11])
Self-definition:
"I'm the Michael Jordan of losing." — Pete ([48:32])

Timestamps for Important Segments

Comedians & Their Names: [00:00], [26:22]
Discussion on Making a “10” of a Show: [07:11]–[08:17]
Eddie Murphy Doc & Vulnerability: [09:04]–[09:39]
Audience Collaboration & Regional Humor: [08:34]–[09:04]
Cutting Jokes for Authenticity: [16:14]–[18:11]
Parenting, Modern vs. Old School: [36:02]–[38:07]
Coolness in Movies: [40:09]–[42:05]
Massage Parlor Story: [53:35]–[59:51]
Working Out for a Cause: [64:31]–[65:56]

Memorable Comedy "Workshop" Moments

Hot Tub Story:
Pete tells a story about a stranger offering up bad jokes in a hotel hot tub; Mike helps him punch up the exchange ([31:07]).

“I also feel like I might get along really well with his wife. You’re my least favorite member of your family, and these are optimal conditions. We’re in a hot tub.” — Pete ([33:08])
Pete’s “Losing” Bit:
Hilarious brainstorming:

“I think people give losers a hard time. ...You don’t exist without me. I’m your god… I’m the Michael Jordan of losing.” — Mike ([48:32])
Denzel Taking Pills Without Water:
Both riff on movie tropes about “coolness,” with Mike dreaming up a combination of cinematic habits to contrast with real life ([40:15]–[41:32]).

Closing Reflection

Pete:

“Vulnerability is everything.”

Mike:

"I listen to [Father Greg Boyle's] books before I do stand-up because I find opening my heart is more important than rehearsing the words." ([65:11])

Cause of the Episode:

Homeboy Industries: Largest gang rehabilitation program in America; ethos of “unconditional love” ([65:36]).

Summary

This wide-ranging, sharp, and emotionally earnest episode epitomizes the blend of joke-craft, honesty, philosophical inquiry, and riotous friendship that defines Working It Out. Mike and Pete navigate the high-wire of writing true, personal material, all while interrogating what makes a joke land, what makes some jokes get “cut,” and why risking vulnerability onstage is, truly, everything.

If you’re a comedy fan, a performer, or just someone fascinated by what makes people (and jokes) tick, this episode is both essential listening and a masterclass in collaboration and self-examination.

Useful Links

Pete Holmes: Instagram, You Made It Weird Podcast
Homeboy Industries: homeboyindustries.org
Mike Birbiglia: Website, YouTube Channel

Note:
For bonus content where Pete and Mike punch up listener-submitted jokes, subscribe to Working It Out Premium.