A failing gym. A villain with frosted tips. A dodgeball tournament on ESPN 8: The Ocho. Just another day in 2004.

The guys throw Kevin into DodgeBall: A True Underdog Story, where Average Joe’s faces off against Globo Gym in the most unnecessary athletic competition ever filmed. Will Kevin embrace the underdog chaos, or will he be overwhelmed by wrench-throwing wisdom and Ben Stiller’s aggressively committed performance?

Starring Vince Vaughn, Ben Stiller, Christine Taylor, Justin Long, and Rip Torn — plus a cameo that makes absolutely no sense but somehow works.

If you can dodge a ball… you can survive this episode.

Getting dumped is hard. Doing it in Hawaii is worse. The guys drop Kevin into Forgetting Sarah Marshall, the breakup comedy where awkward silences last forever, Dracula puppets are emotionally necessary, and running into your ex is basically unavoidable. Will Kevin feel seen by the post-breakup spiral, or just be distracted by the absurd charm of Aldous Snow? Starring Jason Segel, Kristen Bell, Mila Kunis, Russell Brand, and way too much emotional honesty for a vacation.

The safe word is mistletoe. The guys drop Kevin into Four Christmases, the holiday comedy where Vince Vaughn talks fast, Reese Witherspoon panics politely, and every family gathering is its own survival challenge. Will Kevin relate to the chaos of Christmas morning jiu-jitsu, awkward baby names, and pastor Dwight Yoakam… or will he just be looking for the nearest exit? Starring Vaughn, Witherspoon, Jon Favreau, Mary Steenburgen, Robert Duvall, and a whole lot of holiday trauma.

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?