Kevin's First Time

It’s not the O.C.—it’s way weirder. The guys take Kevin back to 2002 with Orange County, a chaotic college-bound comedy starring Colin Hanks and Jack Black. Will Kevin connect with this tale of misunderstood genius and dysfunctional family vibes, or will he just be confused about why everyone’s yelling? With a surprise cameo-packed cast and some seriously early-2000s energy, this one’s all about chasing your dreams… and dodging your burnout brother.

Are you not entertained?! This time, the tables turn as Derik enters the arena for his first-ever watch of Gladiator, the 2000 epic that defined manly revenge cinema. Ryan, Sean, and Kevin guide him through Ridley Scott’s Oscar-winning tale of honor, betrayal, and intense dirt-grabbing. Starring Russell Crowe, Joaquin Phoenix, and a whole lot of slow-motion intensity, the only question is… will Derik finally become a real man?

Good morning, and in case Kevin doesn’t see it: good afternoon, good evening, and good night! The guys pull back the curtain on The Truman Show, the 1998 mind-bending dramedy starring Jim Carrey. Will Kevin buy into the perfect world of Seahaven, or will he start questioning everything… including this podcast? Directed by Peter Weir, this one has existential dread, hidden cameras, and a lot of product placement.

The Dude abides… but will Kevin? The guys dive into the weird, wonderful world of The Big Lebowski, the 1998 cult classic from the Coen Brothers. Will Kevin appreciate the rug that really ties the room together, or will he get lost in the absurdity of nihilists, bowling, and White Russians? Starring Jeff Bridges, John Goodman, Julianne Moore, and Steve Buscemi — this isn’t just a movie, it’s a vibe.

Hellooooo! The guys take Kevin back to 1993 to meet Mrs. Doubtfire, everyone’s favorite unconventional nanny. Will Kevin be charmed by Robin Williams’ iconic performance, or will this family classic be a drive-by fruiting of disappointment? Starring Robin Williams, Sally Field, and Pierce Brosnan, this heartfelt comedy reminds us that family isn’t just about being together — it’s about doing whatever it takes to stay connected.

A romantic comedy. With zombies. The guys introduce Kevin to Shaun of the Dead, the 2004 cult classic that blends horror, British humor, and a surprising amount of heart. Will Kevin grab a pint and wait for this all to blow over, or will he be too confused by why everyone’s acting so weird? Starring Simon Pegg and Nick Frost, this zombie comedy is all about surviving the apocalypse… one laugh at a time.

McLovin, fake IDs, and one epic quest.—Ryan, Sean, and Derik take Kevin back to 2007 with Superbad. Will he relate to the high school chaos, or will the cringe-worthy moments be too much to handle? Starring Jonah Hill, Michael Cera, and Christopher Mintz-Plasse, this coming-of-age comedy is all about friendship, awkwardness, and some seriously bad decisions. Prepare for laughs… and secondhand embarrassment.

Yeah, baby, yeah! The gang introduces Kevin to the shagadelic world of Austin Powers: International Man of Mystery. Will he dig this 1997 spy spoof, or will it leave him saying, “Oh, behave”? Starring Mike Myers in dual roles as the groovy spy and his nemesis, Dr. Evil, this comedy classic is a mojo-filled ride of ridiculous one-liners and psychedelic fun. Groovy, baby!

High five!!! The guys take Kevin on a wild ride through Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan. Will he survive the cringe, or will this 2006 shock-comedy masterpiece break his brain? Starring Sacha Baron Cohen in his most infamous role, this episode is sure to have some awkward pauses and uncontrollable laughter. Very nice…....pause..... NOT!

Stay classy as Ryan, Sean, and Derik introduce Kevin to Anchorman: The Legend of Ron Burgundy. Will he embrace the absurdity of this 2004 comedy classic, or will it be kind of a big deal… in the wrong way? Starring Will Ferrell, Paul Rudd, Steve Carell, and Christina Applegate, this one’s 60% of the time, funny every time.