If you enjoyed the dark comedy and biting satire of 'Whipped' (2000), you'll love these 10 similar movies and shows that explore relationships, dating, and the absurdity of modern romance. This list is perfect for fans of sharp wit and cynical humor.

American Pie (1999)
Description: This film is a quintessential coming-of-age comedy that revolves around a group of high school friends navigating the awkwardness of adolescence, relationships, and sexual exploration. Its humor is both raunchy and heartfelt, making it a staple in the genre.
Fact: The infamous pie scene was improvised by actor Jason Biggs, who was not told what type of pie would be used. The film's success spawned multiple sequels and spin-offs.


Road Trip (2000)
Description: This comedy follows a group of college friends on a wild cross-country trip to fix a romantic mistake. The film's blend of outrageous humor and camaraderie among friends makes it a standout in the genre.
Fact: The film features a cameo by Tom Green, who was a popular MTV personality at the time. The movie was shot in just 28 days, contributing to its raw and spontaneous feel.


Old School (2003)
Description: This comedy centers on a group of middle-aged men who start a fraternity to relive their youth, leading to chaotic and hilarious situations. The film's themes of nostalgia and rebellion resonate with audiences.
Fact: Will Ferrell's streaking scene was largely improvised. The film marked one of the first major roles for Vince Vaughn in a comedy, establishing his signature fast-talking style.


EuroTrip (2004)
Description: A raucous adventure about a group of friends traveling through Europe, filled with over-the-top humor and cultural mishaps. The film's irreverent tone and focus on youthful escapades align well with similar comedies.
Fact: The song 'Scotty Doesn't Know' was written specifically for the film and became a cult hit. The movie was not a box office success but gained a strong following through home video and cable TV.


Wedding Crashers (2005)
Description: A comedy about two friends who crash weddings to meet women, only to find themselves in over their heads when real emotions get involved. The film's mix of humor and romance makes it a memorable entry in the genre.
Fact: The script was inspired by real-life wedding crashers. The film's success helped revive the R-rated comedy genre in the mid-2000s.


Knocked Up (2007)
Description: A story about an unexpected pregnancy that forces two very different people to navigate adulthood together. The film's blend of humor and heartfelt moments about growing up and responsibility is a hallmark of its appeal.
Fact: Many of the film's scenes were improvised, including much of the dialogue between Seth Rogen and Paul Rudd. The movie was a critical and commercial success, solidifying Judd Apatow's reputation as a comedy director.


Forgetting Sarah Marshall (2008)
Description: A breakup comedy that follows a heartbroken man as he tries to move on from his ex-girlfriend, only to find himself stuck at the same resort as her. The film's mix of humor and emotional vulnerability is a key strength.
Fact: Jason Segel wrote the script based on his own experiences with breakups. The film features a full-length puppet musical, which Segel also wrote and performed.


Superbad (2007)
Description: A hilarious and heartfelt story about two best friends trying to make the most of their last days of high school, with a focus on their misadventures and attempts to fit in. The film balances crude humor with genuine emotional moments.
Fact: The characters of Seth and Evan are based on the real-life friendship of the film's writers, Seth Rogen and Evan Goldberg, when they were teenagers. McLovin's fake ID became an iconic pop culture reference.


Pineapple Express (2008)
Description: A stoner action-comedy about two unlikely friends on the run from criminals after witnessing a murder. The film's unique blend of humor, action, and buddy dynamics sets it apart.
Fact: The movie's title refers to a rare strain of marijuana. The film was inspired by classic '80s action movies but with a comedic twist.


The Hangover (2009)
Description: A wild comedy about a group of friends who wake up after a bachelor party with no memory of the previous night and must retrace their steps to find the groom. The film's unpredictable humor and chaotic energy made it a massive hit.
Fact: The film was shot in just 15 days. The tiger in the hotel room was a real tiger, and the scenes with it were carefully choreographed for safety.
