Schwing! The guys take Kevin back to 1992 for Wayne’s World, where public-access TV is king, headbanging is mandatory, and corporate sellouts wear Reebok. Will Kevin party on with Wayne and Garth, or will he end up saying “we’re not worthy” to the soundtrack alone? Starring Mike Myers, Dana Carvey, Tia Carrere, and Rob Lowe, this one’s all about friendship, rock ’n’ roll, and a suspicious amount of licorice.

Hitmen, boxers, and one very mysterious briefcase. The guys throw Kevin into Pulp Fiction (1994), Quentin Tarantino’s cult classic where cheeseburgers are royal, dance contests happen at diners, and Ezekiel 25:17 becomes a battle cry. Will Kevin keep up with the tangled timelines and miracle bullets, or just get lost trying to figure out what’s in the case? Starring John Travolta, Samuel L. Jackson, Uma Thurman, Bruce Willis, and a whole lot of chaos, this one redefined cool.

Two grown men, one house, zero maturity. The guys throw Kevin into Step Brothers (2008), where drum sets are sacred, bunk beds are “so much more room for activities,” and the Catalina Wine Mixer is the biggest deal in town. Will Kevin embrace the chaos of Will Ferrell and John C. Reilly’s man-child antics, or just side with the weary dad trying to hold it all together? Starring Ferrell, Reilly, Mary Steenburgen, Richard Jenkins, and Adam Scott, this comedy is so quotable it just became your best friend.

A family of geniuses. A dad who fakes cancer to win them back. Just another Tuesday in Wes Anderson’s world. The guys invite Kevin into The Royal Tenenbaums (2001), where everyone is sad, stylish, and speaking in perfectly awkward monotone. Will Kevin appreciate the dry wit and quirky charm, or will he just be distracted by all the falcons, tracksuits, and Owen Wilson’s cowboy phase? Starring Gene Hackman, Gwyneth Paltrow, Ben Stiller, and a cast so symmetrical it hurts.

Littering and… podcasting. The guys crack open Super Troopers, the 2001 cult classic packed with mustaches, meow games, and maple syrup chugging. Will Kevin fall in love with these highway hooligans, or will he write them a ticket for excessive absurdity? Created by the Broken Lizard comedy troupe, this one’s dumb, quotable, and—depending on your blood sugar level—hilarious. Meow’s the time to find out.

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.