10 Best Comedies Turning 20 In 2025

Comedy has always been an extremely popular genre of cinema. It has consistently offered audiences a chance to laugh and escape from the troubles of daily life, with both slapstick classics and witty, dialogue-driven powerhouses achieving similar, dopamine-rushed results. Humor driven films have produced timeless gems that continue to resonate today, with few cinematic genres boasting such a rewarding appeal. As the world has just recently been greeted by 2025, now is the perfect moment to revisit some of the best comedy movies of all time that have just celebrated their 20-year milestone of life after release.

Comedy in 2005 was an era of its own. It rolled out numerous effective gut-busters while also flexing its deep variety, as shown through films like Wedding Crashers, Robots, and The Longest Yard. These films not only brought laughter but also checked off different boxes of comedy, striking an imperative balance between clever humor and heartfelt moments. Revisiting these 20-year-old productions offers many a chance to celebrate the polarized, best, lowbrow, and intelligent comedy movies at the same time. These films rival even the most warm comedy TV shows that are good for the soul, proving their lasting legacies.

10

Robots

A Young Inventor’s Quest In A Mechanical World

Rodney Copperbottom, voiced by Ewan McGregor, is America’s most beloved robot inventor. The young dreamer craves to make the world a better place, and his journey to Robot City is one to remember. This film interestingly has jokes for everyone, with family-friendly humor taking the spotlight while adult jokes are subtly sprinkled from time to time. The film also features some serious wit, which overall adds to the timeless charm of Robots. For example, an early version of Rodney makes a cameo as a green robot with a jetpack, showcasing the filmmakers’ attention to detail.

The film’s voice cast includes Halle Berry, Robin Williams, and Mel Brooks. It brings vibrant characters to life with intricate animations inspired by mid-century modern aesthetics, constructing the visually captivating mechanical world of Robots. Overall, this 2005 kiddie coaster is an extremely fun watch for all ages. It has a similar comedic value to The Blue Man Group, who’s featured on the film’s score.

9

The Sisterhood Of The Traveling Pants

Four Friends, One Magical Pair Of Jeans

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The Sisterhood of the Traveling Pants is a 2005 film about four teenage friends—Lena, Tibby, Bridget, and Carmen—who share a pair of jeans that fits each of them perfectly despite their different body types. As they embark on separate summer adventures, the pants become a symbol of their enduring friendship and support. Starring Amber Tamblyn, America Ferrera, Blake Lively, and Alexis Bledel, the film explores themes of growing up and personal discovery.

Release Date

June 1, 2005

Runtime

113 minutes

Director

Ken Kwapis

This heartfelt coming-of-age tale follows four best friends, Lena, Tibby, Bridget, and Carmen. These girls discover a pair of jeans that fits each of them perfectly. Despite their differing body types, this pair of mystical pants acts as a unifying symbol of their unbreakable bond. While wholesomely hilarious, this film also beautifully captures the challenges and triumphs of adolescence. It explores friendship and self-discovery through a lighthearted lens, perfectly reminiscent of wholesome 2005 comedy mixed with a little romance and adventure.

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The cast is extremely talented, with Blake Lively, Alexis Bledel, America Ferrera, and Amber Tamblyn acting as the core four. This film resonated particularly due to its authentic portrayal of teenage life, inspiring a sequel and remaining a beloved staple in the teen drama genre. 20 years later, The Sisterhood of the Traveling Pants has continued to provide audiences with nearly two hours of feel-good entertainment, proving the lasting, yet nostalgic value of comedies centered on friendship and growth.

8

Waiting…

A Day In The Life Of Restaurant Employees

Two decades later, audiences still crave the opportunity to have dinner at ShenaniganZ, the workplace and main setting of the beloved 2005 comedy Waiting…. This film offers a comedic glimpse into the lives of its employees as they navigate eccentric customers, kitchen antics, and personal dilemmas. The film has a spectacular portrayal of the service industry, with staff doing practically anything to pass the time. Raunchy humor and somewhat complex moral issues have raised questions while entertaining audiences, allowing this film to assemble a cult following among its loyal viewers.

Dane Cook improvised his entire character dialogue as well as his name. There was no script, given his total screen time of about three minutes.

The ensemble cast features Ryan Reynolds, Anna Faris, Justin Long and more. These individuals deliver sharp, witty performances that the film simply couldn’t have done without. Many of the film’s scenarios were inspired by real-life experiences of the writers, which adds a reliant layer of authenticity to the outrageous events depicted in this film.

7

Are We There Yet?

A Road Trip Comedy With Unexpected Detours

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Are We There Yet?

Release Date

January 20, 2005

Runtime

89 minutes

Main Genre

Adventure

Cast

Ice Cube
, Nia Long
, Aleisha Allen
, Philip Bolden
, Jay Mohr
, M.C. Gainey

Director

Brian Levant

Are We There Yet? is one of Ice Cube’s most beloved films. The rapper stars as Nick, a bachelor eager to impress his love interest by driving her two children from Portland to Vancouver. Chronicling a realistic road trip littered with comedic disasters, Are We There Yet? possesses the perfect recipe for realistic yet outrageous humor. The children’s antics and nagging behavior coupled with Nick’s inexperience with parenting leads to a series of misadventures all packed into one long trip. It’s hilarious, endearing, and memorable, overall possessing every trait necessary for a great road trip.

The iconic blend of slapstick humor and family dynamics is perfectly mixed together in Are We There Yet? which makes the film as iconic as it is, leading to its sequel Are We Done Yet? as well as a television adaptation. The SUV used in this film is a character of its own, providing unique hilarious mishaps and challenges for the group to form new bonds from, all while allowing the film’s comedic spirit to fly high.

6

Chicken Little

A Small Chicken With A Big Imagination

Chicken Little 2005 poster


Zach Braff’s Chicken Little creates panic when he claims the sky is falling when a piece falls and hits him.Outcast for his claims, Little seeks redemption by joining the baseball team, and plays a key part in winning a crucial game. He’s once again hit by “falling sky” – which turns out to be a UFO – and must convince everyone that he wasn’t lying.

Release Date

November 4, 2005

Runtime

80 minutes

Director

Mark Dindal

Writers

Mark Dindal
, Mark Kennedy
, Steve Bencich
, Ron J. Friedman
, Ron Anderson
, Robert L. Baird

Chicken Little reimagines a classic fable in an even more instantly classic way. The film follows a young chicken who strives to redeem himself after causing a town-wide panic. Ace Cluck, the main character, is voiced by Zach Braff, who perfectly captures the little protagonist’s journey that is focused on bravery, self-belief, and most importantly, humor. Disney’s first fully computer-animated feature deeply resonated with the hearts of audiences, making viewers laugh and feel inspired, all at the same time.

This movie not only marked a shift in animated filmmaking, but also featured a memorable ensemble of characters. Abby Mallard, Runt of the Litter, and Fish Out of Water are all just as contributory to the film as Cluck himself. Aside from its perfect humor, this 20-year-old animated comedy also serves as a revolutionary animated feat. Chicken Little boasts over 76,000 individual feathers, with 55,000 on his head alone. This is just one small way in which the film showcases an intense, deep love for animation, which pairs perfectly with its lovable humor.

5

The Longest Yard

Football, Redemption, And Absurdity Collide

The Longest Yard stars Adam Sandler as a former NFL quarterback who somehow ends up in prison. This film is a remake of a 1974 classic, only done better with a hilarious cast featuring Chris Rock and Burt Reynolds, the original film’s star. Reynolds performed his own stunt during a touchdown run after iconically saying, “I got one run left in me,” an unexpectedly wholesome, legacy-driven moment in this gridiron saga.

Adam Sandler’s strategy to win a football game is similar to his strategy to win at comedy; throw a bunch of misfits together, add some chaos, and let Terry Crews sell people McDonald’s in the huddle. Honestly, it’s less a football team and more of a very angry, very sweaty group therapy session. Nevertheless, it works perfectly. All in all, The Longest Yard is an explosion of pop-culture cemented through undeniably hilarious humor. It blends humor with sports in an all-encompassing, loving way, and features all the great parts of loud, commercial 2005 humor.

4

Kicking & Screaming

A Dad Becomes A Soccer Coach To Bond With His Son

In Kicking & Screaming, Will Ferrell takes on the role of soccer coach for his son’s underdog team. The Tigers lead a comedic journey of growth and personal relationships, which is slightly similar to the themes of The Sisterhood of the Traveling Pants, while hilariously different in virtually every other way. Many of the names on the kids’ jerseys are those of crew members, which adds a personal touch to the production as well as a clever layer of witty humor to compliment the majority of Kicking & Screaming’s occasionally crude, mostly family-based humor.

Exploring parental pressures, generational trauma, and toxic competitiveness in a lighthearted, funny way, this chaotic 2005 hit is less about the beautiful game of soccer and more about a dad who treats a peewee league like the World Cup. With Ferrell yelling at kids like they’re on a million-dollar contract, his true rivalry with caffeine is almost the most hilarious part of the whole movie as he continuously double-fists espressos for approximately one and a half hours.

3

Madagascar

A Hilarious Adventure With Zoo Animals In The Wild

In Madagascar, one of Ben Stiller’s best movies, a quartet of Central Park Zoo residents find themselves stranded on the island of Madagascar. Alex the Lion, Marty the Zebra, Melman the Giraffe, and Gloria the Hippo forever immortalized themselves as beloved characters finding themselves in an unsuspected journey from captivity to the wild. This film is both humorous and heartwarming, providing viewers with an entire menu of emotions that is just as diverse and zany as the animals featured in Madagascar.

Ben Stiller, Chris Rock, David Schwimmer, and Jada Pinkett Smith all bring vibrant personalities to their respective characters, furthering this film’s genius. Sacha Baron Cohen, known for his comedic work with Borat, has a standout role as the world’s most beloved lemur king. He was originally intended as a minor character, but after Baron Cohen improvised eight minutes of dialogue, his two lines expanded into a much larger role. Moments like this perfectly capture the essence of Madagascar; a chaotic yet wholesome powerhouse of a 2005 comedy that will forever remain in the hearts of fans.

2

Wedding Crashers

Two Friends Crash Weddings To Meet Women

In Wedding Crashers, Owen Wilson and Vince Vaughn portray womanizing divorce mediators. This 2005 classic takes the duo’s antics on an unsuspecting rollercoaster full of laughter, drama, and wits. Owen Wilson’s cinematic genius shines in this film, with lines he came up with like “I think we only use ten percent of our hearts,” adding a spontaneous touch to the film’s humor. Other moments of spontaneity like Will Ferrell’s cameo as Chazz Reinhold further emphasize the star-studded, no-rules party of Wedding Crashers.

The film’s success highly derives from its sharp wit and ensemble cast. Christopher Walken and Isla Fisher add further comedic depth to Wedding Crashers’s already bountiful bag of jokes. Wedding Crashers was also the highest-grossing R-rated comedy of 2005, which is especially noteworthy considering the film’s standout position in the early 2000s boom of adult comedies.

1

The 40-Year-Old Virgin

A Man’s Journey To Find Love Later In Life

The 40-Year-Old Virgin’s hilarious yet endearing depiction of a shy electronics store employee’s delayed sexual growth isn’t just an iconic comedy from 2005. It’s an all-time contender with a funny ensemble of characters. The main character Stitzer’s growth is shown through milestone life moments occurring at a rapid pace after years of celibacy. Interestingly enough, Steve Carell lost 30 pounds for the role to showcase Stitzer’s shyness as his main inhibitor of sexual interaction, showcasing the film’s pinpoint attention to detail.

Marking Judd Apatow’s directorial debut as a critical and commercial success, The 40-Year-Old Virgin is praised for its raunchy blend of humor coupled with moments of raw, human emotion. One particularly hilarious scene is Andy’s chest-waxing experience, which was unscripted, which adds to the film’s largely human feel. With a simple yet effective plot, The 40-Year-Old Virgin is by far one of the most iconic comedies turning 20 in 2025.