July 6, 2026

Chappelle on AI, Michelle Wolf’s Comedy Origin, and David Cross on Writing on Stage

Show Notes
Transcript

Johnny Mac delivers Daily Comedy News featuring Dave Chappelle joking to PBS about automation, AI, and people not reading books anymore, then noting he was kidding. Michelle Wolf recounts leaving Bear Stearns-era finance for improv, open mics, and eventually writing for Seth Meyers, Hannibal Buress, and Chris Rock, discussing how “off the table” topics require extraordinary joke craft. Patton Oswalt and David Cross describe developing material on stage and the pressure of constant social-media “authenticity,” with Cross sharing reactions to work-in-progress bits in Brooklyn. Pete Holmes talks about parenting talk, show times, and loving a 2 p.m. talk-show schedule. Gossip Corner covers Sam Harris buying David Spade’s former $32.3M estate and Spade’s TV earnings. The episode also spotlights new specials, Isabel Hagen’s film run, Comedy vs Cancer fundraising.

00:00 Daily Comedy News Intro
00:12 Chappelle on AI Future
00:41 Michelle Wolf Origin Story
01:52 Wolf on Edgy Jokes
02:09 Oswalt on Authenticity
02:46 Old School Joke Writing
03:16 David Cross Live Risks
04:13 Pete Holmes Parenting Bits
04:51 Gossip Corner Spade Money
06:10 New Comedy Specials Today
06:28 Joke Zero Isabel Hagen
07:03 Comedy vs Cancer Update
08:23 Wrap Up and Subscribing
09:06 Ad Free Listening Pitch

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Daily Comedy News with Johnny Mac is a daily podcast covering comedians, stand-up comedy, late night television, and the comedy industry. New episodes every morning. Follow on Apple Podcasts, Spotify, or wherever you listen. Part of the Caloroga Shark Media network.

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This is the animal sanctuary mentioned in the February 10 episode.

WEBVTT

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Caloroga Shark Media. Hi there, I'm Johnny Mack with your

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daily comedy news. Dave Chappelle was speaking to PBS News

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and said, I was talking to a friend of mine

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the other day and we were laughing about how no

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one would really know what to teach a kid now.

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What skill sets are going to matter ten to twenty

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years from now. Is the world becomes automated and everything's

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just changing. I don't know if anyone needs to think anymore.

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The machines are doing all the work for us. It's AI,

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it's quantum computing. Just seems like thinkings for poor people.

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He quickly added, it's a joke, by the way, but

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he did get a little more serious and said, no

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one reads books anymore. It's just so different from when

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I grew up. Amen. Michelle Wolf told her origin story.

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I got a job at bear Stearns in the summer

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of two thousand and seven, a couple weeks after two

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of their hedge funds failed. I was not there at

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the start of the financial crisis. I jumped on the

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sinking ship and it's sink too big to fail, not

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bear Stearns, just the right size. It was more two

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thousand and eight, all the banks were failing. Some friends

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of mine came to visit. We went to a taping

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of SNL. I've always been a big fan. I was like,

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out of the people do this? How do you get here?

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She found out the entire cast had started an improv

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so she signed up for a class. I'd work at

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the bank during the day and then go to an

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improv literally in my heels and skirtsuit. I would do

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improv looking like a business lady. She and some comedy

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minded friends started writing and sharing five jokes a day

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with each other. Posted some of them on Twitter in

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case you're looking for them. She says they were atrocious

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and long since deleted. She started doing open micers and

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then shifted to a part time job, and then her plan.

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I was like, all right, I'm gonna slowly do less

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and less work until I get fired and I left

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my financial career in the dust. By twenty fourteen, she

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was writing jokes for Late Night with Seth Myers and

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for comics like Hannibal Burs. Hannibal recommended her to Chris Rock.

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She wrote for Rock for some of the stuff at

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the twenty sixteen Oscars, her first comedy special Nice Lady

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was for HBO in twenty seventeen, The White House Correspondents

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Dinner in twenty eighteen. Is there anything she considers off

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the table? Quoting Michelle Wolf, she said, I think there

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were jokes where the level of difficulties a lot higher,

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Like if a white person's going to the nword on stage,

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you better have a joke that's so good that everyone's like,

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all right. The level of difficulty for that is extraordinary.

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A lot of people are like, I'm gonna try it,

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and it's like, why, why do you want to try

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it so bad? People think they're being edgy when they're

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just being stupid. Start trek carew in your pat As

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Walt said, you really have to fight for the space

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to observe and withdraw and watch both other people's behavior

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and pay attention to your own. Because it's entertainers especially

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now have less and less non performing time. It feels

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like in order to be an entertainment of the arts,

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you got to be shooting content for your insta, shooting

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stuff for your TikTok. You're performing authenticity. So now authenticity

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is becoming something that drains you. It's gonna be really

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interesting to see how that affects not just comedy, but

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anything where you have to observe life and then reflect

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it back in a unique way when so much of

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your energy is now being taken towards promoting yourself so

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that people look at the stuff when you're saying that

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you're observing reality. He works with a notebook. I'm very

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old school. I have a notebook. I use the classic

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composition notebook with a speckled black and white cover. My

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notebooks are a combination of me writing the beginnings of

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jokes as best I can. I can't sit and write jokes,

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he says, something I'm going to try to do for

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the next album. What I do is I have an idea.

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I just kind of work it out on stage over

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successive nights, and then it becomes a joke. My notebooks

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are all jotted down ideas and clippings of things like

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a picture from a magazine or name I've heard I

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think artists call them a morgue, where you collect pictures

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and images of things that might inspire you or something later.

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So he just collected altogether. It's a weird combination. David

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Cross says, I do not sit down and write jokes.

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I'm just not good at that. I do all my

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writing on stage. Cross says, I've done plenty of stuff

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that is, for lack of a better word, button pushing.

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He was asked if that's fun for him. Oh, yeah,

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I wouldn't do it if it wasn't if it makes

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a set that night memorable and interesting and potentially dangerous.

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I mean, it's live. That's part of the fun of

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doing a live show. During one show, he let the

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audience know that his routine was a work in progress

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and said, by some miracle, all this will turn into

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a good set, a really good set. Once the set

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is together, he'll take it outside of a basement of

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cool people in Brooklyn and bring it to maybe a

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less discerning audience in Kansas or whatever. There's a difference

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between Kansas and Brooklyn, which I think we can all

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agree on. On this particular night, Brooklyn liked an extended

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bit about Charlie Kirk. He got groans for a Holocaust

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joke involving the Nazis co opting Santa Claus. We are

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told another joke quote, boy was I mistaken about what

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a rape kid is? Unquote got a healthy, delayed laugh

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but one about Beast Reality elicited only a middling response.

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Pete Holmes had a conversation with Vulture about his seven

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year old daughter. He said, it's like talking to someone

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who owns a horse, if you're going to talk about

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your horse for five hours, and make sure the other

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person that you're talking to also owns a horse. Meeting

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people without kids typically don't want to hear about kids.

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Pete Holmes says, why would someone need to swashbuckle and

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keep private hours. I'm more in the camp of if

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I could do this job at noon, I'd love that.

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I briefly did It's talk show after conon O'Brien on CBS,

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and I loved it because the shows were always at

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two o'clock in the afternoon. That was proof positive that

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some people visiting Burbank will still laugh at stand up

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comedy even if it's being delivered at two in the afternoon.

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I'd be done at four o'clock, go home, have an

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early dinner, and being bet by nine. It was the

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best on Gossip Corner in Touch magazine reports that podcaster

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Sam Harris has purchased David Spade's former Beverly Hills estate

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worth thirty two point three million dollars, David Spade had money?

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What does Spade have money from? Like? SNL doesn't pay

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that well? Call up Spades, IMDb? Where does he have

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money from? Polis Academy four an appearance in Coneheads. He

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played Scuzz in the animated movie Racing Stripes. How does

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this guy have money? I gotta ask Ai? Hold on hey,

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I says, movies like Tommy Boy, Black Sheep, Jodurt, and

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The Emperor's New Groove paid well and some generate residuals.

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TV was probably his biggest paid a On Just Shoot Me,

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he reportedly earned up to three hundred thousand dollars per

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episode in later seasons, How Long did Just Shoot Me? Run?

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And On Rules of Engagement he reportedly earned about one

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hundred and fifty thousand per episode, but that didn't run long. Podcasting,

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he has co hosted the successful Fly on the Wall

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podcast with Tana Carvey. Sure, and the podcast is doing well.

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And believe me, he lives well. But that's not like

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crazy money. All Right, Just Shoot Me ran on NBC

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from nineteen ninety seven to two thousand and three. All Right,

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I guess he's got Just Shoot Me money ran for

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seven seasons and produced one hundred and forty eight episodes.

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All right, so if he was making three hundred grand,

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so he's making a million every three episodes towards the

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end there. Okay, just shoot me if you need something

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to watch today on YouTube, it's Tamson Kelly's Hot Tity

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Bungalow comedy special. You can ask her about. The title

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also Outsiday Brendan ayres a debut comedy special alive and

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well you'll find that on the eight hundred pound guerrilla

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streaming service Guerrilla Comedy Plus told you about that one

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on Friday. I like the name of this company, Joke zero.

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It is a distribution company. They've announced they've acquired Isabel Higgins.

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On a String and On a String will be in

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theaters starting on the eleventh of September. Boasting a ninety

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one percent critics score in Rotten Tomatoes stemming from a

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successful festival run. It'll get a week long theatrical run

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exclusively at the Quad Cinema, New York City before expanding

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into other markets. On a String follows a Juilliard training

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violist as she navigates the New York City freelance classical

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musician scene, playing gigs that often draw her into the

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personal lives of strangers, all while living with her oddball

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family's NYC apartment. Nice job by Comedy Versus Cancer, They've

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raised two point seven million dollars for blood cancer research.

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The event was held at Jazz at Lincoln Center in

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New York City. New York City is having quite the

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summer huh. This year's show featured appearances from Britt Goldstein,

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Hassan Minhaj, Zoner garg, Nick Krohle, and others, and from

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The Toronto Guardian. They have their series where they check

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in with local comedians, Let's Check In with Brea Habert.

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Bret describes her comedy as confessional things you'd only tell

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a priest to your doctor, but instead I'm saying them

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in front of a group of strangers in a dimly

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lit basement and getting paid and drink tickets and chicken

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wings if I'm lucky. Influences interesting. Listen here, Christopher Guest,

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Monty Python, Bernie Mack. See you didn't think I was

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gonna say Bernie Mack After Christopher gust and Monty Python,

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Bernie mac Kilda Radner, Norm MacDonald, Beth Stelling, Michelle Wolf,

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Tina Fey. Favorite comedian growing up. I loved Amanda Bines

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growing up. Favorite comedian right now. I'm really enjoying great

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list here. Josh Johnson, Chris Fleming, Llowe, Radcliffe, Jeffrey Asthmas

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and Maddi Wiener pre show ritual a crisp diet Coke

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with a lime wedge, Scroll my notes app and question

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why I didn't just go to law school. She's promoting

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her debut album, Big Naturals. You'll find that on Comedy Records,

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and she also hosts a late night stand up show

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at Comedy Bar called ghost Orgy. You'll find her at

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at Uncle Brea on Instagram and TikTok. And that is

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your comedy news coming off a holiday weekend. You know

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how the show works. I'm not trying to kid you now.

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Hopefully this week we'll have some controversies. I'm keeping an

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eye on this whole office thing with Gervaise and the others.

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I told you about that last Thursday. Hopefully they mix

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it up and we'll have something to talk about. We

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will see. So we want to do so you don't

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miss an episode. You want to go to Spotify and

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turn notifications on and then it will send you notification

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probably every morning at three oh five am Eastern, which

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is when you want the notification if you're being honest

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with yourself, and it'll be like, hey, new episode. Actually

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it won't three oh five. It takes like seven minutes

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or so to get through the pipes. I've published it

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at three oh five, but it'll probably show up on

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your phone. Spotify is actually pretty quick Apples a little slower.

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Podcast is a little slower than that, but you know

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by three thirty in the morning you'll have the show

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Eastern time. Oh, which reminds me I'm supposed to be

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reminding you. If you would like the program without commercial interruption,

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what you do is you go to Apple Podcasts. There's

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a better there. It says uninterrupted listening. You click on that,

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and then for five bucks a month you get the

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show with no ads. There's a thirty day free trial

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if you want to try it out. Now. I won't

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bore you with the details, but the commercial free version

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doesn't show up on your phone till about seven thirty

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in the morning. But again, were you really listening at

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four in the morning. Probably not. I know there's a

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couple of people who do these, A couple people who

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work overnights who appreciate that when the show shows up

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on their phone the middle the night. And I appreciate

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you guys listening. But anyway, if you want the show

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commercial free Apple Podcasts undert Listening, thirty day free trial,

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try it out. Maybe you like it. After that, it

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is five bucks a month and I'll see tomorrow