The Best 2000s Comedies Guaranteed To Make You Laugh, Ranked

The Hangover is a comedy that redefined the genre with its wild take on a Las Vegas bachelor party gone awry. Directed by Todd Phillips and released in 2009, the film features a standout ensemble cast including Bradley Cooper, Ed Helms, and Zach Galifianakis, who play three friends retracing their steps after a night of outrageous antics to find their missing groom-to-be, portrayed by Justin Bartha. The film’s chaotic narrative is punctuated by the larger-than-life character of Mr. Chow, a scene-stealing performance by Ken Jeong.

Often cited as one of the best 2000s comedies, The Hangover captivated audiences with its clever script, unexpected twists, and relentless humor. Its success lies in the chemistry among the lead actors and the film's ability to turn a common pre-wedding ritual into an over-the-top adventure. Embedding itself in popular culture with iconic moments and quotable lines, The Hangover offers a hilariously fresh perspective on friendship and the consequences of a night of uninhibited revelry, ensuring its place in the annals of comedy cinema.

Superbad is a coming-of-age comedy that captures the essence of high school angst and the quest for social acceptance. Directed by Greg Mottola and released in 2007, the film was written by Seth Rogen and Evan Goldberg, drawing on their own teenage experiences. It stars Jonah Hill and Michael Cera as best friends Seth and Evan, who navigate a series of misadventures as they attempt to make the most of their remaining time before graduation. The film also helped launch the careers of Emma Stone and Christopher Mintz-Plasse, who leave lasting impressions with their breakout roles.

Renowned as one of the best 2000s comedies, Superbad stands out for its sharp, witty script and genuine portrayal of adolescent friendship. The movie resonates with audiences through its sincere, often cringe-worthy moments, interwoven with heartfelt humor. Superbad succeeds in blending relatable characters, quotable dialogue, and a sense of nostalgia, cementing its status as a cultural touchstone that humorously and accurately depicts the trials and tribulations of teenage life.

Step Brothers is a raucous comedy that delves into the absurdity of delayed adulthood and the unlikely bond formed between two middle-aged, rival step-siblings. Directed by Adam McKay and released in 2008, the film stars Will Ferrell and John C. Reilly as Brennan Huff and Dale Doback, respectively, whose competitive antics escalate to hilarious extremes once they are forced to live under the same roof. The strong supporting cast includes Mary Steenburgen and Richard Jenkins as their baffled, newlywed parents.

The film's place among the best 2000s comedies is well-earned, thanks to its relentless humor, quotable lines, and the palpable comedic chemistry between Ferrell and Reilly. The duo's commitment to their overgrown child personas carves out a niche of comedy that's as endearing as it is ridiculous. Step Brothers thrives on its blend of awkward family dynamics and outlandish scenarios, setting a high bar for slapstick humor and character-driven farce in the era.

Dodgeball: A True Underdog Story is a comedy that embraces the absurd and delights in the ridiculous, showcasing the classic battle of underdogs versus corporate giants. Directed by Rawson Marshall Thurber in 2004, the film stars Vince Vaughn as Peter LaFleur, the laid-back owner of a rundown gym, and Ben Stiller as White Goodman, the egomaniacal owner of the trendy Globo-Gym across the street. Their rivalry comes to a head in a high-stakes dodgeball tournament, with a quirky ensemble of misfits played by Christine Taylor, Stephen Root, and Rip Torn joining Vaughn's team in the comedic clash.

This film clinches its spot as one of the best 2000s comedies thanks to its sharp wit, physical comedy, and unabashed embrace of a uniquely American pastime. Dodgeball has etched itself into the cultural lexicon with its outlandish characters, quotable lines ("If you can dodge a wrench, you can dodge a ball!"), and the ability to balance cringe with charm. Its celebration of camaraderie, determination, and the triumph of the little guy secures its legacy as a comedy that wholeheartedly entertains while rooting for the underdog.

Anchorman: The Legend of Ron Burgundy, starring Will Ferrell, is a comedy set in the 1970s that follows the life of a legendary anchorman and his news team. The film's humor is rooted in its quirky and absurd characters and its satirical take on the world of broadcast journalism and is widely considered to be one of the defining comedies of the mid-2000s.

The 40-Year-Old Virgin is a comedy that deftly combines heartfelt moments with raunchy humor, examining the social pressures surrounding sex and relationships. Directed by Judd Apatow and released in 2005, the film features Steve Carell in a breakout role as Andy Stitzer, an amiable electronics store worker with a little-known secret: he's still a virgin at 40. When his coworkers, played by Paul Rudd, Romany Malco, and Seth Rogen, discover this, a series of comedic escapades ensue as they help Andy navigate the dating scene. The film also stars Catherine Keener as Andy's love interest, adding depth and chemistry to the story.

Widely acclaimed as one of the best 2000s comedies, The 40-Year-Old Virgin stands tall for its blend of crude humor and surprisingly sweet character development. Carell's earnest portrayal of Andy brings a unique tenderness to a film filled with laugh-out-loud moments, ensuring that its comedy is both outrageous and relatable. Its thoughtful take on adult themes, combined with Apatow's directorial knack for balancing comedy with realism, has left a memorable imprint on the genre and solidified the film's status as a modern comedy classic.