Jim Carrey and Jeff Daniels star as two well-meaning but incredibly unintelligent friends, Lloyd Christmas and Harry Dunne, who embark on a cross-country road trip to return a briefcase in Dumb and Dumber. Directed by the Farrelly Brothers, this film is a classic example of lowbrow, slapstick comedy. While it doesn't prioritize 'witty' dialogue in the traditional sense, its humor comes from the sheer absurdity of the characters' actions and their inability to grasp basic concepts. It's a film that relies on physical comedy and over-the-top situations to generate laughs, becoming a touchstone for a certain style of 90s comedy.

Will Ferrell and John C. Reilly star as two coddled, unemployed adults who are forced to live together when their single parents marry in Step Brothers. Directed by Adam McKay, this film leans heavily into the absurd and juvenile, exploring the dynamic of two overgrown children forced into an unwanted sibling relationship. While not focused on traditional 'wit,' the humor comes from the characters' sheer immaturity, their bizarre schemes, and the surprisingly sharp comedic timing between Ferrell and Reilly. It's a film that's unapologetically silly and finds humor in the ridiculousness of its premise.

Napoleon Dynamite is a true original, a quirky, deadpan comedy that found a massive cult following thanks to its unique style and unforgettable characters. Jon Heder stars as the socially awkward, small-town Idaho teenager Napoleon, who helps his friends Pedro and Deb navigate high school life. The humor is subtle, observational, and relies heavily on the bizarre world and mannerisms of its inhabitants. It's a film that's less about punchlines and more about creating a genuinely strange and endearing atmosphere. Did you know the film was shot in just 23 days?

Todd Phillips' The Hangover kicked off a trilogy with its simple yet effective premise: four friends go to Las Vegas for a bachelor party and wake up with no memory of the previous night, a missing groom, and a tiger in the bathroom. The comedy comes from piecing together the chaotic events through a series of increasingly bizarre and hilarious discoveries. While much of the humor is situational and shock-based, the witty banter between the core trio (Bradley Cooper, Ed Helms, and Zach Galifianakis) is a key part of its success and rewatchability. It's a wild ride from start to finish.

Produced by Judd Apatow and starring Kristen Wiig (who also co-wrote the script), Bridesmaids was a groundbreaking hit that proved female-led comedies could be just as raunchy, hilarious, and heartfelt as their male counterparts. Wiig plays Annie, a down-on-her-luck woman asked to be the maid of honor for her best friend (Maya Rudolph). The film excels with its witty observations on female friendships and wedding rituals, alongside some truly outrageous set pieces. The ensemble cast, including Melissa McCarthy in a breakout role, is phenomenal, delivering laugh after laugh.

A quintessential teen comedy from the minds of Seth Rogen and Evan Goldberg, Superbad captures the awkwardness, desperation, and hilarious camaraderie of high school friends on a mission. Michael Cera and Jonah Hill star as two inseparable pals trying to score alcohol for a party before graduation. The dialogue feels authentic and genuinely witty, capturing the specific way teenagers talk and interact. And of course, Christopher Mintz-Plasse steals scenes as the legend, McLovin. It's a raucous, sweet, and genuinely funny look at the end of an era for two friends.

Blue Steel, Le Tigre, Magnum! Ben Stiller's Zoolander is a wonderfully silly and surprisingly enduring comedy about the fashion industry. Stiller plays Derek Zoolander, a dim-witted male supermodel who becomes the target of a plot involving brainwashing and assassination. The humor is derived from the absurd world of high fashion and the even more absurd characters who inhabit it, particularly Will Ferrell's villainous Mugatu and Owen Wilson's rival model, Hansel. It's a film that embraces its ridiculous premise completely, leading to countless quotable lines and bizarre, hilarious situations.

Ben Stiller directs and stars in Tropic Thunder, a hilarious and sharp satire of Hollywood, acting, and war movies. A group of pampered actors gets dropped into a real conflict zone while filming a Vietnam War epic. The film pulls no punches in skewering the industry's egos and absurdities, featuring standout performances, particularly Robert Downey Jr.'s controversial but undeniably funny turn as a method actor who undergoes 'pigmentation alteration.' It's a bold, star-studded comedy that's both action-packed and incredibly witty in its deconstruction of movie-making tropes.

The second film in Edgar Wright's 'Cornetto Trilogy,' Hot Fuzz takes the buddy cop genre and gives it a uniquely British, incredibly witty twist. Simon Pegg plays Nicholas Angel, a high-achieving London police officer reassigned to a seemingly idyllic, crime-free village where things are definitely not as they seem. The film is packed with visual gags, callbacks, and rapid-fire editing that mirrors Angel's sharp mind. It's a brilliant blend of police procedural tropes, action movie cliches, and laugh-out-loud comedy, all delivered with Wright's signature style and Pegg and Frost's fantastic chemistry.

Will Ferrell is at his peak as Ron Burgundy, the ridiculously self-important anchorman of 1970s San Diego in Anchorman: The Legend of Ron Burgundy. Adam McKay's directorial debut is a masterclass in absurd, character-driven comedy, often born from improvisation on set. The film's humor comes from the sheer, unwavering idiocy and chauvinism of its lead characters, contrasted with the slightly more grounded (but still hilarious) Veronica Corningstone (Christina Applegate). The jazz flute scene? The street fight between news teams? Pure comedic gold that cemented its place as a modern classic.

Written by Tina Fey and based on a non-fiction book, Mean Girls is a pitch-perfect satire of high school social dynamics that's become a cultural phenomenon. Lindsay Lohan plays Cady Heron, a homeschooled student who enters public high school and navigates the treacherous world of 'The Plastics.' The dialogue is sharp, insightful, and incredibly funny, dissecting cliques, gossip, and the absurd rules of teenage girls. The film launched countless catchphrases and remains incredibly relevant for its witty take on identity and fitting in (or not) during adolescence. It's fetch.

Edgar Wright's Shaun of the Dead is a bloody brilliant 'rom-zom-com' that seamlessly blends genuine scares with sharp, witty British humor. It's a loving homage and clever subversion of the zombie genre, following average bloke Shaun as he tries to win back his girlfriend and reconcile with his stepdad during a sudden zombie apocalypse. The film is packed with visual gags, recurring jokes, and foreshadowing that rewards attentive viewers. Did you spot all the hints about the plot in the opening scenes? Simon Pegg and Nick Frost's chemistry is the heart of the film, making this not just funny, but surprisingly sweet and thrilling too.

The Dude abides. Joel and Ethan Coen's The Big Lebowski is less a plot-driven narrative and more a hang-out movie with some of the most quotable, idiosyncratic dialogue ever written. Jeff Bridges stars as Jeff 'The Dude' Lebowski, a laid-back slacker mistaken for a millionaire, leading to a series of bizarre encounters in 90s Los Angeles. The film's cult status is entirely earned thanks to its endlessly rewatchable scenes, unforgettable characters like Walter Sobchak (John Goodman) and Donny (Steve Buscemi), and a vibe that's just effortlessly cool and hilariously absurd. It's a true original that gets funnier with every viewing.

Prepare for a joke-a-second onslaught! Airplane! isn't just a comedy; it's a masterclass in rapid-fire gags, sight gags, and non-sequiturs that somehow coalesce into a hilarious parody of disaster movies. Directed by the Zucker, Abrahams and Zucker trio, this film practically invented a style of spoof that's been imitated endlessly but rarely equaled. The deadpan delivery from dramatic actors like Leslie Nielsen, Robert Stack, and Lloyd Bridges is half the genius. Did you know the directors cast these serious actors precisely because their straight-faced reactions made the absurd situations even funnier? It's pure, unfiltered comedic energy that holds up brilliantly decades later.