Kevin's First Time

Two brothers. A band. A season of change.This week, the guys watch May It Last: A Portrait of the Avett Brothers, directed by Judd Apatow and Michael Bonfiglio. The documentary follows Scott and Seth Avett as they navigate recording with producer Rick Rubin, touring, marriage, fatherhood, and the tension between creativity and real life.Starring Scott Avett, Seth Avett, Bob Crawford, and Rick Rubin, this intimate portrait offers a behind-the-scenes look at the cost — and beauty — of building something that lasts.A different kind of episode.

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?

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.

Ryan, Sean, Derik rewatch the 1999 cult classic 'Office Space' and see if Kevin has enough flare to enjoy it as much as we do. 'Office Space' starring Ron Livingston, Jennifer Anniston, Stephen Root, Gary Cole and directed by Mike Judge

We slap the bass and see if Kevin feels like he missed out on this 2009 bromantic comedy. 'I Love You, Man' - starring Paul Rudd, Jason Segal and Rashida Jones.