The 15 Best Comedy Movies of the Last 25 Years, Ranked
November 9, 2026 4,071 views

The 15 Best Comedy Movies of the Last 25 Years, Ranked

By James Mitchell
From slapstick to deadpan humor, comedy reigns as one of the most versatile film genres, always offering something for every kind of movie fan. Since the early days of movies, comedy has been one of cinema's first popular genres, serving as a humorous escape for audiences; today, it remains just as cherished, if not mo

From slapstick to deadpan humor, comedy reigns as one of the most versatile film genres, always offering something for every kind of movie fan. Since the early days of movies, comedy has been one of cinema's first popular genres, serving as a humorous escape for audiences; today, it remains just as cherished, if not more so.

There have been hundreds of monumental comedies but, when it comes to the last decade and a half, there are a handful of titles, such as Wedding Crashers, Borat, and Bridesmaids, that rank higher than the rest. Even though there are countless comedies that successfully raked in the laughs, hits like The Hangover, The 40-Year-Old Virgin, and Anchorman: The Legend of Ron Burgundy far exceeded moviegoers' expectations with outrageous scenarios and non-stop laughter.

We're the Millers is a raunchy comedy starring Jason Sudeikis as David Clark, a small-time weed dealer who, after being robbed of his product, must travel to Mexico to pick up his supplier's latest shipment. To cross the border without arousing suspicion, Clark recruits a fake family: his stripper neighbor, Rose (Jennifer Aniston); a no-nonsense runaway, Casey (Emma Roberts); and a socially awkward teenager, Kenny (Will Poulter), leading them on a wild, unexpected road trip.

We're the Millers was released when R-rated comedies were thriving, and despite mixed reviews, the movie was a box office success, grossing over $200 million. The cast's chemistry is the real heart and soul of the movie, with each bringing their own unique style of comedy to the table and essentially keeping audiences invested from start to finish. Even though the film's humor is initially rather aggressive, the movie gradually turns into a story of misfits who become a family, creating a warmth that softens the crude jokes and outrageous scenarios.

21 Jump Street is a hilarious buddy-cop comedy based on the hit '80s show of the same name and stars Channing Tatum and Jonah Hill as rookie cops, Greg Jenko and Morton Schmidt, who go undercover as high school students to try and shut down a dangerous drug ring. Compared to other comedies at the time, 21 Jump Street stands out because it knows exactly the kind of movie it is and constantly pokes fun at Hollywood's resilience in reboots and remakes, subtly winking at the audience without becoming smug.

21 Jump Street was a major success, with many critics praising both Hill and Tatum for their performances. The bromance between Hill and Tatum's characters is what ultimately carries the movie, specifically the role reversal, which sees Tatum's character, a former popular jock, struggle to fit in while Hill's character, a former nerd, thrives with his classmates, essentially giving the movie real emotional stakes. It also didn't hurt the movie to have a few unexpected cameos by original stars of the show, Johnny Depp and Peter DeLuise, who bring the perfect touch of nostalgia to the film.

What We Do in the Shadows is a mockumentary horror comedy that follows a group of vampires and roommates, Viago (Taika Waititi), Vladislav (Jemaine Clement), and Deacon (Jonny Brugh), who try to navigate their way through the modern world while also showing a recently turned human, Nick (Cori Gonzalez-Macuer), some of the perks of being undead. The movie was both a critical and commercial success, and in 2019, it was adapted into a television series by FX and ran for six successful seasons.

At the time, vampires were popular subjects of the entertainment world, but unlike the rest, What We Do in the Shadows delivers a fresh and clever take on the concept that ultimately sets it apart from the crowd. The central joke never runs out of fuel, and the premise of immortal, centuries-old vampires who are petty, vain, and bad at modern life is one with endless variations. They struggle to get into clubs without being invited, they argue about chores, and what to wear for a night out, which audiences can surprisingly relate to on a certain level.

The 2003 comedy Old School earns a place on the list because it captured the best of the early-2000s "Frat Pack" era and turned a simple premise into a comedy that people still quote on a regular basis today. The movie follows an attorney, Mitch Martin (Luke Wilson), who, after discovering his fiancée's infidelity, tries to start over and moves into a house that happens to be near a local college campus. As Mitch settles into his new life as a bachelor, his friends Frank (Will Ferrell) and Beanie (Vince Vaughn) decide to turn his place into a party pad and eventually start their own fraternity.

While the premise of Old School seems a bit absurd, the concept of being able to relive your glory days with all the recklessness and lack of good judgment is irresistible to audiences, making it one of the best comedies of the last 25 years. The entire cast is an endless stream of comedy gold, notably Ferrell, who delivers a career-defining performance as Frank "The Tank", while Vaughn's fast-talking charm and Wilson's low-key sincerity round the trio out. Quotes, such as "You're my boy, Blue!" and "Ear muffs!", have since become staples in pop culture, with many fans still quoting the movie even decades later.

The 2008 comedy Tropic Thunder is a ruthless and fearless satire of Hollywood that also happens to be relentlessly funny. Ben Stiller directs and stars as a washed-up action hero, Tugg Speedman, who is cast in an epic Vietnam War movie alongside an intense method actor (Robert Downey Jr.), a drug-addicted comedian (Jack Black), and a rapper with aspirations for the big screen (Brandon T. Jackson). When production is delayed, the director decides to send the actors into the jungle, where they will be filmed by hidden cameras, leading to a series of unfortunate events that eventually land the unknowing group in a real war zone.

The greatest strength of Tropic Thunder is its unwavering commitment to the bit. The fake trailers that open the film, the unhinged jokes, and Oscar bait all show a movie that is unafraid to push the boundaries even if it involves taking shots at the industry itself. While the entire cast delivers sidesplitting performances, Tom Cruise's eccentric performance as the profane, bald studio boss Les Grossman nearly steals the show. Even though the movie earned some backlash, no amount of criticism can diminish how bold, outrageous, and endlessly quotable Tropic Thunder remains to this day.

Simon Pegg stars in the action comedy, Hot Fuzz, as an elite police officer in London, Nicholas Angel, whose successful track record makes the rest of his unit look bad, ultimately resulting in him being transferred to a small rural village. Once Angel arrives in his less desired area, he's soon assigned to investigating a series of brutal murders, adding a bit of an exciting silver lining to his situation.

Hot Fuzz is a hysterical homage to the traditional buddy cop film featuring the humorous dynamic of Pegg and Nick Frost, who originally caught audiences' attention with the parody film, Shaun of the Dead. The duo has a unique chemistry that is both comfortable and natural, conveying a convincing comedic duo that is one of the best in recent years. Aside from a few negative reviews, Hot Fuzz was overall well received by audiences and critics, who commended the film's use of clichés and puns of the traditional buddy cop genre.

South Park creators, Trey Parker and Matt Stone, return to the big screen with the puppetry comedy, Team America: World Police, which is an over-the-top satire on the traditional action film. The film follows a special counterterrorism force that recruits a Broadway actor to help them save the world from Kim Jong Il and his coalition of terrorists and Hollywood's elite.

Inspired by the British science-fiction series, Thunderbirds, Team America had no problem catching audiences' attention with its unusual use of puppetry and miniature effects, which conveyed Parker and Stone's signature style of comedy and antics. The movie has been regarded as one that will both offend and incite laughter in audiences, showing zero hesitation about the levels of offensive insults and exaggerated depictions of famous names. Team America earned generally positive reviews from critics, who praised its bold comedic formula of offending everyone on an equal scale.

Funny man, Judd Apatow, made his directorial debut with the outlandish romantic comedy, The 40-Year-Old Virgin, which stars Steve Carell as a middle-aged electronics employee, Andy, who is mortified when his co-workers discover he's still a virgin. Unwilling to let it go, Andy's co-workers help him find a woman to take his virginity, but as they set him up with disaster after disaster, Andy manages to find a woman who is more than just a one-night stand.

While the initial plot of the film seems a bit vulgar, The 40-Year-Old Virgin does have a sentimental side and a series of outstanding performances by an all-star cast, including Seth Rogen, Jane Lynch, and Paul Rudd, that are impossible to deny as comedy gold. The 40-Year-Old Virgin takes an uncomfortable, sensitive subject and makes it approachable for audiences with its genuine and lighthearted humor, making it one of the best comedies in the last decade and a half.

The mockumentary, Borat, was a cultural phenomenon that became one of the most talked-about movies of the year, earning a reputation for its improvised humor and overly offensive scenarios by Sacha Baron Cohen. Cohen stars as the titular character, a reporter from Kazakhstan who travels to the United States to make a documentary. Throughout his journey, Borat manages to piss off and offend everyone he crosses paths with, resulting in an unpredictable series of events.

Borat is noted for Cohen's improvised interactions with people who are genuinely under the impression that he is from another country and filming a documentary about America. This leads to uninhibited, uncensored, and outlandish scenes that are the definition of unhinged comedy. Surprisingly, Borat earned positive reviews from critics, including Peter Travers of Rolling Stone, who stated, "You won't know what outrageous is until you see Borat. High-five!"

Kristin Wiig stars as a single woman, Annie, whose life is an utter mess, ranging from having to move back in with her mom to losing her bakery. When her best friend, Lillian (Maya Rudolph), gets engaged, she's asked to be her maid of honor, which she graciously accepts, but she has her work cut out for her as she finds herself competing against Lillian's new, wealthy, and elite friend, Helen (Rose Byrne).

Bridesmaids is hands down one of the funniest and most entertaining movies of the last 25 years that accurately conveys the classic frienemy dynamic between women in an honest and hilarious light. While the movie is full of unforgettable, laugh-out-loud moments, it also has immense heart and, in the end, essentially reveals that everyone has their own batch of insecurities and problems in life. Bridesmaids reigns as the perfect rendition of the ups and downs of womanhood and friendship, blended with unhinged, raunchy comedy that never gets old.