Best Comedy Films of 1998
- HaHa Jokester
- Jun 19
- 6 min read
Updated: Jun 20
1998 was a year where comedy pushed boundaries—whether through shocking gross-out gags, tender romantic surprises, or absurdist animation. The Farrelly brothers changed what mainstream audiences would laugh at, while indie filmmakers and rising stars infused comedies with a personal, sometimes bittersweet edge. From prom disasters to Big Lebowski chaos, 1998 was a reminder that laughter could be loud, weird, sharp, or deeply human.
The Comedy Landscape in 1998
Gross-Out Goes Mainstream
There’s Something About Mary shocked audiences and delighted critics, kicking off a wave of envelope-pushing comedy that would define the next few years.
Rom-Coms with a Twist
While still popular, romantic comedies like You've Got Mail and Sliding Doors leaned into irony, digital age anxiety, and narrative experimentation.
Cult Classics Are Born
1998 gave us several comedies that underperformed at the box office but became cult sensations on home video—chief among them The Big Lebowski.
Top 10 Comedy Films of 1998
There’s Something About Mary
Runtime: 2hr 10min
A lovelorn man hires a private investigator to track down his high school crush, only to find unexpected competition and chaos.
Ted still pines for Mary, the girl he had a disastrous prom night with years ago. He hires a sleazy private detective to find her, but the investigator falls for her too—kicking off a series of increasingly absurd suitors vying for Mary's heart. With its outrageous gags, offbeat charm, and breakout performance by Cameron Diaz, this Farrelly Brothers comedy became a cultural touchstone of late '90s humor.
The Big Lebowski
Runtime: 1hr 57min
A laid-back slacker known as "The Dude" gets caught up in a bizarre kidnapping plot due to a case of mistaken identity.
Jeffrey "The Dude" Lebowski is a stoner who just wants his rug back, but he finds himself tangled in a complex mystery involving a missing wife, nihilists, a porn empire, and a wealthy namesake. Directed by the Coen Brothers, The Big Lebowski is a surreal, quotable, and endlessly rewatchable cult classic that mixes absurdism with noir parody in unforgettable fashion.
Rushmore
Runtime: 1hr 33min
An eccentric prep school student wages war with a middle-aged industrialist over the affections of a first-grade teacher.
Max Fischer is a wildly overcommitted student at Rushmore Academy, where his obsession with extracurriculars and a crush on a teacher lead him into rivalry with Herman Blume, a disillusioned businessman. Wes Anderson's Rushmore blends deadpan humor, stylized visuals, and emotional depth, establishing Anderson's unique voice and launching Jason Schwartzman's career alongside a reinvigorated Bill Murray.
You've Got Mail
Runtime: 1hr 59min
Two rival bookstore owners fall in love online, unaware of each other's real-life identities.
Kathleen Kelly and Joe Fox are bitter business rivals in the real world—she owns a small indie bookstore, while he's part of a corporate chain. Unbeknownst to them, they've also been anonymously corresponding via email and developing a genuine romantic connection. Nora Ephron's charming romantic comedy, starring Tom Hanks and Meg Ryan, updated The Shop Around the Corner for the digital age with heart and wit.
The Truman Show
Runtime: 1hr 43min
A man unknowingly lives his entire life inside a reality TV show until he begins to suspect the truth.
Truman Burbank lives in the idyllic town of Seahaven, unaware that his entire world is a fabricated set and that everyone around him is an actor. As he begins to question his reality, he sets out on a journey of self-discovery and rebellion. Jim Carrey gives a surprisingly restrained and moving performance in this prescient satire of media, surveillance, and identity, directed by Peter Weir.
Dr. Dolittle
Runtime: 1hr 30min
A doctor rediscovers his childhood ability to talk to animals—and chaos ensues.
After a car accident, Dr. John Dolittle discovers he can communicate with animals, turning his orderly medical practice upside down as creatures big and small flock to him for help. Eddie Murphy’s comedic timing and charisma anchor this family-friendly reimagining of the classic tale, blending slapstick antics with a warm message about embracing who you are.
Sliding Doors
Runtime: 1hr 39min
A woman’s life splits into two parallel realities depending on whether or not she catches a train.
In Sliding Doors, Helen’s story diverges into two timelines based on a seemingly minor moment—missing or catching a subway train. Each path explores how her relationships, career, and self-perception evolve under different circumstances. Gwyneth Paltrow shines in this romantic dramedy that blends fate, chance, and self-empowerment into a thoughtful narrative experiment.
BASEketball
Runtime: 1hr 48min
Two childhood friends invent a hybrid sport and accidentally create a national phenomenon.
From South Park creators Trey Parker and Matt Stone, BASEketball is a raunchy satire in which two slackers turn their backyard game—a mix of baseball and basketball—into a major league sensation. The film skewers sports commercialization while leaning hard into absurdist gags, juvenile humor, and a surprising amount of heartfelt bromance.
A Night at the Roxbury
Runtime: 1hr 22min
Two dim-witted brothers dream of getting into the hottest nightclub in town and launching their own.
Based on the popular SNL sketches, A Night at the Roxbury follows Steve and Doug Butabi—lovably clueless brothers with a passion for nightlife—as they stumble their way into VIP culture and aim to open their own club. With infectious '90s dance music, head-bobbing routines, and goofy charm, the film became a cult favorite despite its critical reception.
Half Baked
Runtime: 1hr 22min
A group of stoners turn to drug dealing to bail their friend out of jail, leading to unexpected misadventures.
When their friend is imprisoned for accidentally killing a police horse, three pothead roommates—led by Dave Chappelle—start selling stolen medical marijuana to raise bail money. Half Baked leans into silly gags and surreal sequences, gaining cult status thanks to its quotable lines, stoner logic, and Chappelle’s standout comedic voice.
Underrated Picks Worth Your Time
Living Out Loud
Runtime: 1hr 40min
Holly Hunter and Danny DeVito star in this funny, moving story about rediscovery and friendship, anchored by jazzy style and emotional intelligence.
Living Out Loud is a reflective, character-driven dramedy about Judith Moore, a recently divorced woman reevaluating her life after her husband leaves her for another woman. Set in New York City, Judith embarks on a journey of self-discovery, forming unexpected friendships—including with her building’s elevator operator, Pat—while navigating loneliness, midlife reinvention, and the complexities of emotional vulnerability. With a jazz-infused atmosphere and introspective tone, the film blends humor and melancholy, anchored by Holly Hunter’s nuanced performance and supported by Danny DeVito’s quietly affecting role.
Buffalo ’66
Runtime: 1hr 50min
Vincent Gallo’s dark, deadpan character study blends awkward humor with quiet tragedy, creating something weirdly hypnotic and unforgettable.
Buffalo ’66 is a darkly comic and emotionally raw indie film that follows Billy Brown, a recently released convict who kidnaps a young woman, Layla, and forces her to pose as his wife to impress his emotionally distant parents. As the two spend an uneasy day together in Buffalo, their strange dynamic shifts into something unexpectedly tender and sincere. Directed by and starring Vincent Gallo, the film mixes gritty visuals, offbeat humor, and bursts of vulnerability to explore themes of dysfunction, regret, and the human need for connection.
Zero Effect
Runtime: 1hr 56min
A modern-day detective story with comic noir overtones—Bill Pullman and Ben Stiller shine in this brainy, under-the-radar gem.
Zero Effect is a quirky, modern detective story centered on Daryl Zero, an eccentric and reclusive private investigator who solves cases with brilliance but struggles with basic human interaction. Hired to investigate a mysterious blackmail scheme, Zero enlists his long-suffering assistant Steve Arlo as a go-between, only to find the case complicated by unexpected emotional entanglements. Blending mystery, dry humor, and character study, the film—written and directed by Jake Kasdan—offers a fresh, offbeat take on the classic detective archetype, with a standout performance by Bill Pullman as the socially inept sleuth.
Comedy Highlights & Trivia
Hair Gel Scene = Comedy History
There’s Something About Mary broke taboos and box office records with its infamous scenes—forever changing what studios would greenlight.
"That rug really tied the room together."
Though barely noticed on release, The Big Lebowski became a cult phenomenon with fan conventions, memeable quotes, and endless rewatches.
Indie Royalty Emerges
Rushmore signaled the arrival of Wes Anderson as a major creative force, blending stylized comedy with real emotional weight.
Where to Watch These Today
There’s Something About Mary – Max, Starz
The Big Lebowski – Peacock
Rushmore – Disney+, Hulu
You've Got Mail – Prime
The Truman Show – Pluto tv
Sliding Doors – Peacock, Tubi
BASEketball – Prime
Half Baked – Prime
Buffalo '66 – Criterion Channel
Closing Thoughts
1998 was a defining year for modern comedy—crass yet clever, ironic yet sincere. It gave us instant classics, slow-burn cult favorites, and game-changing weirdness that reshaped what comedy could be. Whether you were falling in love through email, bowling with nihilists, or watching Ben Stiller survive the worst prom ever, the best comedies of 1998 left a lasting impression—equal parts outrageous and brilliant.
