Best Comedy Films of 1999
- The Finest Reviewer
- Jun 20
- 7 min read
1999 was a landmark year for cinema—and comedy was no exception. As film pushed into the new millennium, comedies grew bolder, smarter, and more self-aware. The year was filled with teen rebellion, workplace disillusionment, and subversive laughs that masked deeper themes. From pie mishaps to office rage to emotionally awkward romances, 1999 delivered one of the most varied and memorable years in comedy history.
The Comedy Landscape in 1999
Teen Comedies Get a Reboot
American Pie brought raunchy teen comedy back into the spotlight, but this time with a surprising dose of heart and self-awareness.
Workplace Dread Hits Big
Office Space captured late-‘90s corporate malaise with deadpan brilliance, becoming one of the most quoted cult classics of its era.
Rom-Coms Take Risks
From gender reversals to mental health twists, 1999’s romantic comedies like 10 Things I Hate About You and Runaway Bride didn’t play it safe.
Top 10 Comedy Films of 1999
American Pie
Runtime: 1hr 35min
A group of high school friends make a pact to lose their virginity before graduation, leading to a series of awkward and hilarious misadventures.
American Pie became a defining teen comedy of its era by blending gross-out humor with surprising emotional sincerity. Centered on four friends navigating the chaos of sex, love, and embarrassment in their final year of high school, the film mixes iconic moments (like the infamous pie scene) with relatable teenage insecurities. Its ensemble cast and raunchy-yet-heartfelt tone struck a chord with audiences, sparking a successful franchise and setting the blueprint for 2000s teen comedies.
Office Space
Runtime: 1hr 29min
A disillusioned office worker rebels against corporate monotony with a scheme that hilariously spirals out of control.
Office Space is a sharply observed satire of white-collar drudgery that turned TPS reports, red staplers, and soul-crushing cubicles into pop culture landmarks. Directed by Mike Judge, the film follows Peter Gibbons, a fed-up tech employee who, after a hypnotherapy session, stops caring about work—ironically gaining promotions and inspiring a plan to embezzle money. Though it was a modest box office performer, its dry wit and workplace truths made it a cult classic, especially among the chronically overworked.
10 Things I Hate About You
Runtime: 1hr 37min
A modern high school reimagining of The Taming of the Shrew, where love, deception, and rebellion collide.
Set in a Seattle high school, 10 Things I Hate About You reinterprets Shakespeare’s The Taming of the Shrew with charm, wit, and teenage angst. Julia Stiles and Heath Ledger shine as fiercely independent Kat and mysterious bad boy Patrick, whose romance is orchestrated through a web of matchmaking, lies, and genuine chemistry. With sharp dialogue, standout performances, and a killer soundtrack, the film became a beloved teen rom-com that balances literary inspiration with late-'90s sensibilities.
Election
Runtime: 1hr 43min
An overachieving student’s campaign for class president sparks an all-out war with her bitter teacher.
In Election, Alexander Payne crafts a darkly funny and biting satire about ambition, ethics, and the absurdity of high school politics. Reese Witherspoon delivers a career-defining performance as Tracy Flick, a hyper-driven student whose run for student body president is sabotaged by her frustrated civics teacher, played by Matthew Broderick. What begins as a petty grudge escalates into a ruthless chess match that skewers both youthful idealism and adult hypocrisy, making it one of the smartest comedies of the decade.
Galaxy Quest
Runtime: 1hr 42min
Washed-up sci-fi TV actors are mistaken for real heroes by aliens and must live up to their on-screen personas.
Galaxy Quest brilliantly parodies Star Trek fandom while doubling as a heartfelt love letter to it. The film follows a cast of forgotten sci-fi television stars who are kidnapped by naïve aliens believing their fictional adventures were real historical documents. Thrust into an interstellar conflict, they must rise to the occasion and become the heroes they only pretended to be. Packed with laughs, affection for geek culture, and standout performances from Tim Allen, Sigourney Weaver, and Alan Rickman, it's a clever and unexpectedly touching gem.
Notting Hill
Runtime: 2hr 4min
A shy London bookseller unexpectedly falls in love with a world-famous actress.
Notting Hill delivers a quintessential romantic fantasy grounded in awkward charm and endearing performances. Hugh Grant plays the affable bookstore owner whose mundane life is upended when Hollywood superstar Anna Scott, played by Julia Roberts, strolls into his shop. Their relationship unfolds with humor, heartbreak, and a dose of fairy tale magic, exploring the surreal clash of celebrity and ordinary life. With its now-iconic moments and emotional sincerity, the film became an instant classic of modern romance.
Austin Powers: The Spy Who Shagged Me
Runtime: 1hr 35min
Time-traveling superspy Austin Powers returns to stop his nemesis Dr. Evil from stealing his “mojo.”
In this sequel to the 1997 hit, Mike Myers doubles down on absurdist humor, outrageous characters, and groovy nostalgia. The Spy Who Shagged Me sees Austin Powers travel back to the 1960s to retrieve his stolen mojo, encountering eccentric foes like Mini-Me and allies like Felicity Shagwell. The film revels in slapstick, innuendo, and satirical digs at spy tropes, with Myers once again playing multiple roles to riotous effect. It became a pop culture phenomenon, cementing Austin as a comedic icon of the era.
Analyze This
Runtime: 1hr 43min
A powerful mob boss starts therapy and drags his reluctant psychiatrist into a chaotic double life.
Analyze This hilariously blends mafia drama with therapy-room confessions in a high-concept comedy anchored by Robert De Niro and Billy Crystal. De Niro plays Paul Vitti, a crime boss plagued by anxiety attacks, who enlists the help of psychiatrist Ben Sobel, who’s horrified to be pulled into mob life. The film thrives on its clash of genres, poking fun at gangster archetypes while exploring vulnerability in hyper-masculine spaces. Their unlikely chemistry turns the film into both a laugh-out-loud comedy and a clever character study.
Runaway Bride
Runtime: 1hr 56min
A journalist investigates a woman who keeps ditching grooms at the altar, only to fall for her himself.
Reuniting Julia Roberts and Richard Gere after Pretty Woman, Runaway Bride offers a familiar yet charming romantic comedy about second chances and self-discovery. Roberts plays Maggie Carpenter, infamous for fleeing weddings, while Gere’s cynical reporter aims to expose her story. As he digs deeper, what begins as a hit piece evolves into mutual introspection and unexpected romance. Though formulaic, the film is elevated by its charismatic leads and a crowd-pleasing blend of humor and heart.
Bowfinger
Runtime: 1hr 37min
A desperate filmmaker secretly shoots a movie starring a paranoid action star who doesn’t know he’s in it.
Bowfinger is a clever Hollywood satire that skewers the industry’s vanity, delusion, and desperation. Steve Martin stars as Bobby Bowfinger, a down-on-his-luck producer who devises an outrageous plan: film a sci-fi movie with top star Kit Ramsey (Eddie Murphy), without his knowledge. Murphy doubles as Kit and his nerdy lookalike, delivering a masterclass in comedic range. With sharp writing and affectionate absurdity, Bowfinger is a meta-comedy about dreamers, schemers, and the fine line between brilliance and madness.
Underrated Picks Worth Your Time
Dick
Runtime: 1hr 34min
A teen-girl twist on the Watergate scandal, Dick turns political history into goofy fun—with standout performances by Kirsten Dunst and Michelle Williams.
Dick is a sly and irreverent political satire that reimagines the Watergate scandal through the eyes of two clueless teenage girls. When best friends Betsy and Arlene (played by Kirsten Dunst and Michelle Williams) accidentally stumble upon the infamous break-in, they’re unwittingly pulled into the Nixon White House as official dog walkers—and later, the mysterious informant “Deep Throat.” Blending bubbly teen comedy with sharp historical parody, Dick cleverly mocks 1970s politics, media manipulation, and presidential paranoia, all while delivering a surprisingly subversive and charming coming-of-age story.
Man on the Moon
Runtime: 1hr 58min
Jim Carrey gives a career-defining performance as oddball comedian Andy Kaufman—equal parts hilarious and haunting.
Man on the Moon is a biographical drama that explores the life, career, and enigmatic persona of comedian Andy Kaufman, brought to life through a transformative performance by Jim Carrey. Directed by Miloš Forman, the film blurs the lines between reality and performance, mirroring Kaufman’s own refusal to conform to traditional comedy. From his rise on Taxi to elaborate pranks and confrontational routines, the film delves into his relationships, insecurities, and the mystery of his final years. Both a tribute and a character study, Man on the Moon captures the brilliance and frustration of an entertainer who defied expectations at every turn.
Mystery Men
Runtime: 2hr 2min
A team of wannabe superheroes led by Ben Stiller in a spoof that was ahead of its time—absurd, clever, and visually bold.
Mystery Men is a quirky, offbeat superhero comedy about a ragtag group of misfit vigilantes who must save their city after the capture of its real superhero. Featuring an ensemble cast led by Ben Stiller, William H. Macy, and Janeane Garofalo, the film satirizes the superhero genre with characters like Mr. Furious (whose power is uncontrolled rage) and The Shoveler (who fights crime with a shovel). When the arrogant Captain Amazing is kidnapped by his arch-nemesis, it’s up to these unlikely heroes to step up—despite their lack of actual powers. Full of absurd humor and stylized visuals, Mystery Men is a cult classic that celebrates the weird, the underdog, and the power of teamwork.
Comedy Highlights & Trivia
“This one time… at band camp…”
American Pie shocked and delighted with gross-out gags, but its character warmth made it a defining teen comedy for a new generation.
Red Staplers and TPS Reports
Mike Judge’s Office Space quietly flopped at the box office but exploded on home video—forever changing how we talk about cubicle life.
Sci-Fi Comedy Done Right
Galaxy Quest blended Star Trek parody with real heart, earning critical love and cult classic status over time.
Where to Watch These Today
American Pie – Starz
Office Space – Hulu
10 Things I Hate About You – Disney+
Election – Flix
Galaxy Quest – Pluto tv
Notting Hill – Max
Mystery Men – Prime
Closing Thoughts
1999 didn’t just close out a decade—it redefined how comedy could work going forward. It was a year when laughs came with layers: satire with substance, slapstick with soul, and weirdness that felt authentic. Whether you were dodging TPS reports, storming Area 51 with washed-up TV stars, or delivering a Shakespeare update in high school, the best comedies of 1999 gave us bold ideas and unforgettable characters—with punchlines that still hit.
