Comedy has remained one of the most beloved and enduring genres in cinema, providing audiences with valuable doses of laughter and an escape from everyday stresses. From timeless slapstick to clever, dialogue-driven films, this genre has consistently proven its ability to elicit joy and engage viewers emotionally. As we enter 2025, it’s an opportune time to delve into some of the greatest comedy films that have just celebrated their 20th anniversary, revealing their unique contributions to the cinematic landscape.
The Era of Comedy in 2005
Reflecting on the comedy landscape of 2005, we find a wealth of films that not only tickled funny bones but also showcased a diverse range of comedic styles. Notable titles such as Wedding Crashers, Robots, and The Longest Yard struck a harmonious balance between lighthearted humor and poignant storytelling. These films offer a nostalgic trip down memory lane, bringing back the charm of both lowbrow and intelligent comedy that resonates deeply even two decades later.
10 Robots
A Young Inventor’s Quest In A Mechanical World
In Robots, voiced by the talented Ewan McGregor, we are introduced to Rodney Copperbottom, a passionate inventor on a mission to improve the world in which he lives. This animated masterpiece combines humor that caters to all ages, showcasing family-friendly jokes alongside subtle adult humor. The meticulous attention to detail, like a cameo from a classic early version of Rodney, amplifies the film’s charm.
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9 The Sisterhood Of The Traveling Pants
Four Friends, One Magical Pair Of Jeans
The Sisterhood of the Traveling Pants follows four inseparable best friends—Lena, Tibby, Bridget, and Carmen—who discover a pair of jeans that miraculously fits each of them perfectly. While this film delves into the trials of adolescence, it simultaneously delivers wholesome humor, capturing the essence of friendship and self-discovery. With a stellar cast that includes Blake Lively and America Ferrera, this film significantly resonates with audiences, inspiring a sequel and securing its place in the teen drama genre.
8 Waiting…
A Day In The Life Of Restaurant Employees
Waiting… provides a comedic snapshot of the life of restaurant workers at ShenaniganZ. This film cleverly navigates through the whimsical dynamics of staff interactions, eccentric customers, and personal trials faced in the service industry. With raunchy humor and insightful moral questions, it has cultivated a dedicated cult following who appreciate its authenticity due to scenarios drawn from real-life experiences.
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7 Are We There Yet?
A Road Trip Comedy With Unexpected Detours
Featuring Ice Cube, Are We There Yet? takes viewers on a chaotic excursion as he attempts to impress his love interest by driving her children from Portland to Vancouver. This film encapsulates the humor and heartwarming moments inherent in family road trips, highlighting the misadventures that arise due to the children’s antics and the dad’s lack of parenting experience.
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6 Chicken Little
A Small Chicken With A Big Imagination
Chicken Little, Disney’s first fully computer-animated film, retells a classic fable with a vibrant twist. Voiced by Zach Braff, this young chicken’s journey toward redemption offers a delightful blend of humor and life lessons pertaining to bravery and self-belief. The film’s visual appeal—down to its intricately animated characters—reinforces its status as a remarkable achievement in animated storytelling.
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5 The Longest Yard
Football, Redemption, And Absurdity Collide
In The Longest Yard, Adam Sandler finds himself as a former NFL quarterback turned prisoner. As a richly comedic remake of the 1974 original, it showcases an ensemble cast, including Chris Rock and legendary actor Burt Reynolds, who makes a memorable return. This film artfully blends hilarity with heart, revolving around the themes of redemption and teamwork.
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4 Kicking & Screaming
A Dad Becomes A Soccer Coach To Bond With His Son
Kicking & Screaming stars Will Ferrell as a passionate soccer coach trying to connect with his son through sport. This film stands out for its physical comedy and relatable parenting dynamics, showcasing a father who treats a youth league like the World Cup. With hilarious and chaotic scenes, the film simultaneously addresses serious themes of competitive culture and personal growth.
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3 Madagascar
A Hilarious Adventure With Zoo Animals In The Wild
Madagascar brings to life a quartet of Central Park Zoo animals—Alex, Marty, Melman, and Gloria—as they navigate the wild after a twist of fate. This dazzling comedy, with stellar voice performances from stars like Ben Stiller and Chris Rock, delivers both humor and heart in a story of friendship and discovery away from the comforts of home.
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2 Wedding Crashers
Two Friends Crash Weddings To Meet Women
Wedding Crashers stars Owen Wilson and Vince Vaughn as two lifelong friends crashing weddings in search of romance. This film is a quintessential example of 2005’s comedy landscape, filled with sharp wit, memorable one-liners, and a talented ensemble including Christopher Walken and Isla Fisher. Its undeniable humor made it the highest-grossing R-rated comedy of that year.
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1 The 40-Year-Old Virgin
A Man’s Journey To Find Love Later In Life
The 40-Year-Old Virgin presents a touching, yet hilarious portrait of a man navigating his late-blooming journey towards love and self-acceptance. With Steve Carell headlining a quirky ensemble, the film expertly blends raunchy humor with genuine moments of humanity. One of its most iconic scenes—Andy’s unscripted chest-waxing—perfectly illustrates the film’s commitment to authenticity and the relatable challenges of adult relationships.
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