8. Wedding Crashers (2005)
The 2005 filmWedding Crasherscame out at the height of Frat Pack popularity. Starring Vince Vaughn and Owen Wilson, the movie centers on two men who show up to weddings uninvited so they can have sex with the single women there afterwards.
It’s a hilarious and surprisingly heartwarming comedy that has a great cast supporting the two leads: Rachel McAdams, Bradley Cooper, Isla Fisher, Christopher Walken, and Will Ferrell.
The biggest laughs come from Ferrell’s cameo as a guy who crashes funerals with the same intent as Wilson and Vaughn’s characters. And while it lacks a certain imagination, it delivers on every level you’d want from a Frat Pack comedy.
Related:The Best Movies About Weddings, Ranked
7. Zoolander (2001)
Zoolanderwas one of the films that started the Frat Pack’s mainstream climb. Combining Ben Stiller with his old buddy Owen Wilson—who both play dense, egotistical fashion models—Zoolanderis a wild ride through the dark underbelly of male modeling.
The plot revolves around Ben Stiller’s character, Derek Zoolander, and the attempts of fashion designer Mugatu (played by Will Ferrell) to brainwash him into killing the Prime Minister of Malaysia.
The film is unquestionably iconic in its style and has brilliant performances from its principal cast. While there are some great cameos in the movie, none are better than the late David Bowie’s hilarious role as a fashion judge.
Related:The Dumbest Movie Characters Who Are Still Lovable
6. Talladega Nights: The Ballad of Ricky Bobby (2006)
Will Ferrell and John C. Reilly have made a fantastic comedy duo over the years. At the height of the Frat Pack era, they both came together on several projects, includingTalladega Nights.
The film tells the story of Nascar driver Ricky Bobby (and his best friend Cal Naughton Jr.) as Bobby’s career falls apart due to the appearance of a new driver, Jean Girard.
The humor is dialed up to eleven in the film, and Ferrell puts in one of his career-best performances. Reilly, too, is on top form alongside the supporting cast featuring Sacha Baron-Cohen, Amy Adams, Gary Cole, and Michael Clarke Duncan.
Related:The Most Rewatchable Movies of All Time, Ranked
5. Dodgeball: A True Underdog Story (2004)
One of the most enduring comedy movies of the past 20 years,Dodgeballsaw Vince Vaughn and Ben Stiller lead a wonderfully wacky cast to box office success.
When Average Joe’s Gym is about to be taken over by arch-nemesis Globogym, the hodgepodge bunch of misfits that call it home seek a way to save it: by winning the Las Vegas dodgeball tournament.
In terms of sheer comedy value,Dodgeballis special. There isn’t one aspect of it that could be changed to make it a better movie, and everybody involved in production knew that—even the great Chuck Norris, who makes an iconic cameo in the film.
Related:The Best Underdog Movies of All Time
4. Old School (2003)
Old Schoolis one of the least-known Frat Pack movies, especially compared to the cultural sensations later in this article. But as far as comedic heft is concerned, it’s up there with the best.
Starring Luke Wilson, Will Ferrell, and Vince Vaughn, the movie centers on Luke Wilson’s Mitch, who leaves his girlfriend after he finds out that she partakes in regular threesomes while he’s away.
Mitch ends up moving into a house located close to the local university, and chaos ensues when his friends turn it into a frat house to prevent Mitch from being kicked out of it.
It was released at the height of the Frat Pack’s success and was critically and commercially successful—so much so that Will Ferrell and Vince Vaughn’s careers bumped up a few notches afterwards.
3. Tropic Thunder (2008)
As the Frat Pack years began drawing to a close, Ben Stiller gathered some of the gang together for one of the biggest (and funniest) comedy movies they’d ever make.
Tropic Thunderhas a meta premise that features a group of pampered Hollywood actors that get lost in the jungle while filming their new war movie—and then get caught up with an actual international drug ring where they have to fight their way out for real.
The film was a great achievement for everybody involved, and Robert Downey Jr. received an Academy Award nomination for his role as Kirk Lazarus, but the MVP was Tom Cruise’s Les Grossman who “negotiates” with the drug cartel!
2. Anchorman: The Legend of Ron Burgundy (2004)
The Frat Pack’sAvengers-style moment came in the 2004 iconic hit movieAnchorman. By way of cameos and supporting roles, the whole Pack turned up at some point in this movie, save for Owen Wilson.
The story of an acclaimed news team and their debonair leader Ron Burgundy,Anchormanis a comedy like no other. Set in the 1970s, a beloved San Fransisco news team is put under pressure by the arrival of a career-driven newswoman, Veronica Corningstone.
The film has become a cult classic and it even spawned a sequel in 2013. While everybody has their own favorite parts of the film, the mass fight-to-the-death sequence with the various news outlets of San Fransisco is downright legendary.
Related:The Best Movies About Journalism and Media, Ranked
1. The Royal Tenenbaums (2001)
None of the Frat Pack movies has ever toppedThe Royal Tenenbaums. Written by Owen Wilson and Wes Anderson—who both received Academy Award nominations for it—the film centers on a family of geniuses who have failed to live up to their potential.
Wes Anderson’s vivid direction gives the film a unique look while Ben Stiller, Owen Wilson, and Luke Wilson comprise the Frat Pack contingent alongside Gene Hackman, Bill Murray, Anjelica Huston, Gwyneth Paltrow, and Danny Glover.
The film has aged into one of the best-made movies of the 21st century. It has become a part of pop culture, with fans often dressing as the characters at events like Comic-Con.
Read next:The Greatest Ensemble Movie Casts of All Time, Ranked
