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Weekend Update: Pennywise the Clown on Gen Z Wellness Parties
SKETCH-O-VISION
A VERY GOOD USE OF YOUR TIME.
The setup
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The premise
Here’s the bit.
Michael Che brings on Pennywise the Clown to weigh in on Gen Z's sober daytime wellness parties. The child-eating entity insists he has changed: he has left the sewer for a shared loft in Austin, spends his days coding, working out and flexing for Che, and has launched an AI startup that swaps a single red balloon for armies of digital ones. When Che accuses him of plugging a tech company, Pennywise explains that he takes the form of each person's worst fear, and for Che that turns out to be an intervention, complete with a group of concerned loved ones and Colin Jost reading a letter about Che's drinking.
The funny people
Meet the cast. 3
Say it with us
Highly quotable.
Newsflash, man, men can evolve.
I don't live in a sewer anymore. I live in a loft in Austin, Texas, with three other motivated young Christians.
We all watched your special, or as I like to call it, your cry for help.
A little extra
Notes from the archive.
This aired on SNL's October 31, 2026 Halloween episode hosted by Inde Navarrette, where Ben Marshall's Pennywise pitched an AI startup called WeAllFloat.ai.
Script
Automatically generated script; wording may contain errors. Speaker labels are inferred.
- 00:00
Michael Che
According to CNN, some Gen Z students are throwing daytime wellness parties as an alternative to parties with drugs and alcohol. Here to comment is Pennywise the Clown.
- 00:11
Pennywise ?
Come What's up on, dude. Yeah.
- 00:17
Michael Che
Hi, Pennywise. Why are you here to talk about Gen Z wellness parties?
- 00:22
Pennywise
Because I'm about that life now, Che. I will say it till the cows come home, man. You don't need to drink to have fun. Look at Che, man. He's like, huh, huh, you don't?
- 00:33
Michael Che
No, I'm not. And what are you talking about? Aren't you, like, a clown that kills kids?
- 00:38
Pennywise
Oh, you're familiar with my work. Oh, thank you, big homie, yeah. Look, man, I gotta go where the kids are, bruh. And look, am I technically an ancient malevolent entity? Sure. Do I shapeshift to entrap children and eat their souls? I have. But newsflash, man, men can evolve. Okay, I don't live in a sewer anymore. anymore. I live in a loft in Austin, Texas, with three other motivated young Christians. And when we're not on Claude Code building epic stacks, we're having long talks with our shirts off and doing hella burpees. Check these gains, man. Feel that. Feel that, man. I'm not gonna squeeze your arm. Just give that a feel, man. I'm not gonna squeeze your arm. Do it, Jay. Please. All right. Still a clown, man. But yeah, dog, that's what I'm up to, man. Got a little crew crew together of cool, like-minded, sober, predatory tech guys, and we started a company. It's called WeAllFloat.ai. Instead of trapping one kid with one balloon, what if you had hundreds of AI agents, each with their own digital balloons, using the habit-forming technology from the homies over at DraftKings?
- 01:52
Michael Che
Dude, is that why you're here? To promote your new tech startup?
- 01:56
Pennywise
up no i'm here because i manifest as people's worst fears which for you is this you have a lot of people who care about you in this world che who are concerned about you
- 02:10
Michael Che
um is this an intervention
- 02:14
Pennywise
Yeah, man. yeah man it sure is we all watched your special or as i like to call it your cry for help Help. Colin?
- 02:26
Colin Jost
Dear Michael, your drinking has affected me in the following way.
- 02:32
Michael Che
No, Pennywise the Clown, everybody.
- 02:35
Pennywise ?
Let's go!
- 02:36
Michael Che ?
No. Let's go. I'm not gonna quit.
The rabbit hole continues
One more couldn’t hurt.
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