During the late 90s and early 2000s, we saw a shift in the culture of comedy movies. Groups like The Pythons weren't dominating the scene with their films, and stars like Adam Sandler were breaking out and growing big in Hollywood.
But the greatest cultural shift in comedy movies came with one particular raft of new talent—a group of comic actors who signaled the start of a new era for Hollywood.
Ben Stiller. Owen Wilson. Vince Vaughn. Jack Black. Steve Carell. Paul Rudd. Have you heard of them? They all began starring in movies together. And along with Will Ferrell, they launched a legendary epoch of box office domination.
They came to be known as "The Frat Pack," which was itself an homage to "The Rat Pack" of the 1950s—an iconic group of singers featuring Frank Sinatra, Sammy Davis Jr., and Dean Martin.
While the Frat Pack no longer collaborates as often as they once did, there was a time—mainly in the mid-2000s—where everything the Frat Pack touched became box office gold. Many of them are still riding that wave today, just in their own unique ways.
Let's take a stroll down memory lane and remember the best Frat Pack movies ever made. You'll be laughing like never before!
8. Wedding Crashers (2005)
Directed by David Dobkin
Starring Owen Wilson, Vince Vaughn, Rachel McAdams
Comedy, Romance (1h 59m)
The 2005 film Wedding Crashers came 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.
7. Zoolander (2001)
Directed by Ben Stiller
Starring Ben Stiller, Owen Wilson, Christine Taylor
Comedy (1h 30m)
Zoolander was 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—Zoolander is 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.
6. Talladega Nights: The Ballad of Ricky Bobby (2006)
Directed by Adam McKay
Starring Will Ferrell, John C. Reilly, Sacha Baron Cohen
Comedy, Sport (1h 48m)
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, including Talladega 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.
5. Dodgeball: A True Underdog Story (2004)
Directed by Rawson Marshall Thurber
Starring Ben Stiller, Christine Taylor, Vince Vaughn
Comedy, Sport (1h 32m)
One of the most enduring comedy movies of the past 20 years, Dodgeball saw 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, Dodgeball is 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.
4. Old School (2003)
Directed by Todd Phillips
Starring Luke Wilson, Vince Vaughn, Will Ferrell
Comedy (1h 28m)
Old School is 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)
Directed by Ben Stiller
Starring Ben Stiller, Jack Black, Robert Downey Jr.
Action, Comedy, War (1h 47m)
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 Thunder has 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)
Directed by Adam McKay
Starring Will Ferrell, Christina Applegate, Steve Carell
Comedy (1h 34m)
The Frat Pack's Avengers-style moment came in the 2004 iconic hit movie Anchorman. 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, Anchorman is 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.
1. The Royal Tenenbaums (2001)
Directed by Wes Anderson
Starring Gene Hackman, Gwyneth Paltrow, Anjelica Huston
Comedy, Drama (1h 50m)
None of the Frat Pack movies has ever topped The 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.