Jamie Kennedy’s return to Undressed is like a double shot of espresso—smooth, bold, and a little wild. In this second part of our 100th episode, Jamie opens up about love, money, and the kind of bag that can make a grown man tear up. He paints a cinematic picture of gifting his “Audrey Hepburn” of a girlfriend a $4,000 Louis Vuitton from the Beverly Center—the shriek, the joy, the protective hook for the bag in her car—and then confesses he’s eyeing a Birkin next (“thirty grand, chumps!”). It’s the kind of moment that makes you laugh while tugging at your heart, especially as he reveals she didn’t grow up with nice things and now cherishes every detail.
From there, the convo swings from the surreal (Jamie’s jaw dropping at a military parade featuring Kim Jong-un, Xi Jinping, and Putin) to the hilarious (banter about whether “the gays” would make jail “pretty” and Martha Stewart’s jail doilies) to pure Hollywood gossip—like the shocker that Sabrina Carpenter’s aunt is actually Bart Simpson (Nancy Cartwright!) and the low-key fortune Jennifer Tilly made off The Simpsons.
But the real pulse of this episode beats in Jamie’s vulnerability. He opens up about losing both parents, downsizing his life pre-COVID, Alyssa moving in, their pandemic ping-pong and naked sunbathing, and his current crossroads: rebuying his old Los Feliz home or starting fresh in Beverly Hills, Vegas, or even New Orleans. It’s a midlife-meets-career confession that feels both raw and refreshingly unfiltered.
Then comes the mystical twist. During his live coffee reading, a heart literally forms at the bottom of his cup—Pol' and Patrik see it too—and the energy in the studio shifts. The reading nudges Jamie toward love, partnership, and maybe even fatherhood (“Alyssa would be such a good mom”), as he wrestles with whether to finally “put a ring on it.” It’s intimate, disarming, and strangely prophetic.
Of course, the episode isn’t all tears. Jamie dives headfirst into Runway Rundown, roasting and raving over Sophie Turner’s sultry “I’m single” lace look, Chloe Sevigny’s “Halloween Horror Nights” couture disaster, Austin Butler’s 1975 porn-leather misstep, and even his own past fashion crimes (a black mesh headbanded ensemble he swears was for Kicking It Old School, but the hosts say screams “Motherlode at 3 a.m.”). The mix of self-deprecation and bold honesty is pure Jamie.
By the end, you’ve laughed at Missy Elliott booting him out of a Phantom, gasped at the Seminole Hard Rock “death suite” he unknowingly slept in, and leaned forward as he weighs buying Raven-Symoné’s Porsche. It’s the ultimate Jamie Kennedy blend—Hollywood chaos, heartfelt confessions, and a coffee reading that feels like a cosmic mic drop.
This is another Hurrdat Media Production. Hurrdat Media is a podcast network and digital media production company based in Omaha, NE. Find more podcasts on the Hurrdat Media Network by going to HurrdatMedia.com or the Hurrdat Media YouTube channel!
💬 Best Quote:“Let’s just kick it and see where the ding-a-lings go.” — Jamie Kennedy, on “experimenting” with Snoop Dogg
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