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.

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.

Meet the Parents is a comedy that delves into the relatable dread of meeting one's potential in-laws, pushing the limits of awkward family encounters. Directed by Jay Roach and released in 2000, the film stars Ben Stiller as Greg Focker, a male nurse who endures a series of mishaps in his effort to impress his girlfriend's formidable father, Jack Byrnes, played with deadpan perfection by Robert De Niro. The dynamic between Stiller and De Niro is complemented by a strong supporting cast, including Teri Polo, Blythe Danner, and Owen Wilson.

Earning its reputation as one of the best 2000s comedies, Meet the Parents masterfully balances physical comedy with the tension of social faux pas. Its success is driven by a universal theme and the convincing performances of its cast, particularly De Niro's turn as an intimidating, lie-detector-wielding ex-CIA father. The movie's clever, cringe-inducing humor and memorable catchphrases ("I have nipples, Greg, could you milk me?") have made it a staple in the genre, resonating with anyone who's ever felt the pressure of making a good first impression.

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.