If you enjoyed the raw honesty and dark humor of A Complete History of My Sexual Failures (2008), this list is for you. We’ve curated 10 similarly candid and comedic films and shows that explore love, relationships, and personal misadventures with unflinching humor. Whether you're a fan of self-deprecating documentaries or cringe-worthy romantic comedies, these picks will keep you entertained.

American Pie (1999)
Description: A classic teen comedy that revolves around the awkwardness and misadventures of high school students trying to lose their virginity, filled with cringe-worthy yet relatable moments.
Fact: The infamous pie scene was filmed using a real pie, and the actor had to do multiple takes. The film's success spawned multiple sequels and a franchise.


Old School (2003)
Description: A comedy about a group of grown men trying to relive their college days, filled with outrageous antics and awkward sexual and social situations.
Fact: Will Ferrell's streaking scene was improvised. The film was inspired by the real-life experiences of the writers and their friends.


Anchorman: The Legend of Ron Burgundy (2004)
Description: A satirical comedy about the absurdity of male ego and workplace dynamics, featuring plenty of cringe-worthy and hilarious moments of personal and professional failure.
Fact: The film's script was originally over 150 pages long, with many scenes cut for time. The news team's fight scene was one of the most expensive scenes in the movie.


Wedding Crashers (2005)
Description: A comedy about two friends who crash weddings to meet women, leading to a series of hilarious and awkward romantic and sexual encounters.
Fact: Vince Vaughn and Owen Wilson improvised many of their scenes together. The film's success helped revive the R-rated comedy genre in the mid-2000s.


Knocked Up (2007)
Description: A comedy that delves into the consequences of a one-night stand, blending crude humor with genuine emotional moments about responsibility and unexpected relationships.
Fact: Many of the film's scenes were improvised, including much of the dialogue between Seth Rogen and Paul Rudd. The movie was shot in just 12 weeks.


Forgetting Sarah Marshall (2008)
Description: A humorous yet heartfelt look at breakups and the struggles of moving on, featuring awkward romantic encounters and self-deprecating humor about personal and sexual failures.
Fact: Jason Segel performed the full-frontal nude scene in one take. The Dracula puppet musical was entirely Segel's idea and was included in the script from the beginning.


Superbad (2007)
Description: A raunchy coming-of-age comedy that explores the awkwardness and hilarity of teenage sexual experiences and relationships, with a focus on male friendship and the pressures of adolescence.
Fact: The script was written by Seth Rogen and Evan Goldberg when they were just 13 years old. Jonah Hill and Michael Cera improvised many of their lines, adding to the film's natural humor.


Zack and Miri Make a Porno (2008)
Description: A raunchy yet sweet comedy about two friends who decide to make a pornographic film to solve their financial problems, exploring themes of friendship, love, and sexual awkwardness.
Fact: The film's title caused controversy, leading some theaters to refuse to show it. Many of the adult film actors in the movie were actual porn stars.


The Hangover (2009)
Description: A wild comedy about a group of friends dealing with the aftermath of a night of debauchery, filled with outrageous and embarrassing situations that test their friendships.
Fact: The film was shot in just 15 days in Las Vegas. The tiger in the movie was real and had to be sedated during filming.


I Love You, Man (2009)
Description: A bromantic comedy that focuses on the challenges of male friendship and the awkwardness of forming new relationships, with plenty of cringe-worthy and heartfelt moments.
Fact: Paul Rudd improvised many of his lines, including the famous 'slappin' da bass' scene. The film's title was inspired by a real-life phrase used by the director's friend.
