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Jamie Kennedy: "You can go viral, but it's the grind is what makes you good"

Jamie Kennedy

Jamie Kennedy on Hosting Comics, Hitting 50, and Going Full McConaughey

Jamie Kennedy’s voice comes in hot and fast, like a guy who just walked off stage and is still riding the high. Which is fair—he’s hosting the eighth season of Coming to the Stage, dropping a new comedy special called Stupid Smart on Tubi, and somehow still making time to talk about Tremors sequels, the genius of Hannah Gadsby, and whether or not Bradley Cooper would punch him in the face.

“I think Cooper would get mad,” Kennedy jokes, when asked if he’d ever do his impersonation of the actor to his face. “But McConaughey? McConaughey would laugh. He’d give me tips. Cooper would be like, ‘Yeah, okay, shut up.’”

That’s the energy of Stupid Smart—equal parts “how the hell did I end up here?” and “how do I get out alive?” The special is a tight hour of callbacks, self-deprecation, and Kennedy turning career bruises into punchlines. “You start with a joke, then you build a joke, then a few jokes, then a segment,” he says, namechecking Dick Gregory like a man with a blueprint taped to his wall. “Then you build an hour. That’s what I tried to do. Start light, build, then drop some thoughts.”

Those “thoughts” include dating disasters, AI paranoia, and the surreal experience of playing Michael Gross’s son in Tremors 5 & 6. “Michael’s a trained Chicago actor. He’s very precise. I’m a loosey-goosey nut,” Kennedy says. “He’s like, ‘Here’s the map of the market stands we’re visiting.’ And I’m like, ‘Bro, this one has falafel, let’s start here.’ But it works. That dynamic is real. He’s the dad. I’m the idiot. Boom.”

Kennedy’s been around long enough to know the difference between 15 minutes and real staying power. He’s seen how TikTok and YouTube warp the old math of earning your stripes. “You used to have to grind,” he says. “Get up at the Roxy, hope someone heard your song, get a deal. Now, you go viral. That’s your tape. Doesn’t mean you’re good, just means you’re seen.”

But he’s not bitter. Not even close. He’s fascinated. “You can get the credits before you get the skills,” he says. “But the grind—that still matters. The grind is what makes you good. 10,000 hours still counts.”

If the special is about resilience, it’s also about timing. Kennedy turned 50 during the pandemic. “Couldn’t throw a party. Couldn’t even leave the house,” he says. “So yeah, the pressure was off. It was great.”

There’s also a reverence lurking under the goofball exterior. Kennedy lights up talking about the greats: Carlin, Pryor, Chappelle, and most surprisingly, Hannah Gadsby. “She did 20 minutes on Picasso and blew my mind,” he says. “People were like, ‘That’s not stand-up.’ And I was like, ‘That’s art. That’s education. That’s hilarious. She wrecked me in the best way.’”

He says he doesn’t watch many specials these days—not because he’s above it, but because he’s trying not to be accidentally derivative. Still, Gadsby made the cut. “She made trauma digestible. That’s what great comics do. That’s what I’m aiming for.”

In the end, Kennedy’s special feels like a prelude to something bigger. He’s already thinking about the next one. “There are five levels of comedy,” he says. “I think I’m on level four. The next one? That’s when I try to convince people to think like me.”

God help us.

Listen to the interview above and then check out the videos below.

Kyle is the WFPK Program Director. Email Kyle at kmeredith@lpm.org

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