The 1990s were a righteous decade full of advancement that yielded a slew of memorable cinematic titles, like these 10 must-watch witty comedies of the 90s.
Next to the 80s (thanks to John Hughes), the 90s was a decade full of technological innovation and advancement that yielded a slew of some of the most memorable movies of the 20th century. From action-packed thrillers and advanced horror flicks to sappy dramas, Westerns, and comedies, it was a fabulous decade in the evolution of silver screen content.
While there are plenty of noteworthy titles that stand out, none stand out as much as witty comedies. They tend to stick with us the most because they’re intellectually humorous and quotable with their timely one-liners and culturally relevant dialogue. Here are 10 must-watch witty comedies of the 90s, in alphabetical order. Every single one of these movies are favorites in my personal collection.
1. As Good as It Gets (1997)
Director: James L. Brooks
The first time I saw As Good as It Gets, I fell in love with its snarkiness, its portrayal of mental health and how those with an affliction are observed and treated, and its timely sincerity. It’s littered with distinct personalities and impressive, clever dialogue, offering a fresh perspective on human behavior and the world around us.
Melvin Udall (Jack Nicholson, of The Shining) is an obsessive-compulsive, misanthropic romantic fiction writer who is pretty much rude and sour to everyone he meets, regardless of who it is. His main goal in life is to give sh*t to everyone, and he does so with the utmost fervor. Everyone hates him, and he hates them, so you’ll enjoy watching as he navigates the people and chaos of New York City.
Nicholson’s penchant for unfiltered witty dialogue, apathy, dry humor, and cynicism kept me rolling, because it reminded me that, deep down inside of all of us, there’s a little Melvin Udall just waiting to be let out … and who deserves to be, from time to time.
You’ll love the clever dialogue and witty retorts, and by the end of the movie, you’ll be wondering how, if this really is as good as it gets, you can make your life better.
*Also features one of the wittiest movie lines ever: Where’d they teach you to talk like this? In some Panama City, sailor-wanna-hump-hump bar? Or is it get-away day and your last shot at his whiskey? Sell crazy someplace else; we’re all stocked up here. –Melvin Udall
2. Clerks (1994)
Director: Kevin Smith
Ah, the 90s hit that spoke for all Gen-Xers across the planet with its clever dialogue, subtle humor, well-developed characters, and social commentary.
The directorial debut of Kevin Smith, Clerks focuses on a day in the life of a convenience store clerk, who’s not even supposed to be there. Brian O’Halloran stars as Dante, the best Quick Stop store clerk in New Jersey.
To help him pass the time on his day off, his friend Randal (Jeff Anderson, of Clerks III) hangs around, observing Quick Stop customers while neglecting his own customers next door at the video store. Their uneventful day is interrupted by news that one of Dante’s exes has died. After attending her memorial service, Dante muses over whether he should stay with his current girlfriend or reunite with his ex, all in a day’s work.
Clerks is witty and crude in its cynical celebration of everyday life (as it were in the 90s), poignantly capturing the malaise and frustration of young adults in dead-end jobs. Its realistic portrayal of hum-drum existence mixed with relatable characters and situations resonated with audiences and launched the View Askewniverse, a shared cinematic universe featuring recurring characters and storylines.
3. Clueless (1995)
Director: Amy Heckerling
Thanks to its sharp dialogue and its irreverent, satirical humor, Clueless is one of the wittiest comedies of the 90s that had girls everywhere muttering under their breath, “Ugh, as if!”.
Alicia Silverstone, of Reptile, stars as Cher Horowitz. She’s shallow, rich, and socially worshipped, not just because she’s beautiful, but also because she’s extremely intelligent and delightfully witty. She’s the most popular girl at her Beverly Hills high school, where she also sees herself as a matchmaker.
After successfully coaxing two teachers into dating each other, she sets her sights on a new project. When she gives a makeover to the clumsy new girl, Tai (Brittany Murphy, of Girl, Interrupted), Cher slowly awakens to the misguidedness her older, ex-step brother Josh (Paul Rudd, of Ant-Man and the Wasp: Quantumania) warned her about as she watches Tai climb to the top of the social ladder. In the process of examining her existence, Cher is dethroned, but that doesn’t matter; she’s too busy falling for Josh.
Clueless reminds us that life is all about figuring out who you are and navigating those ups and downs with wit and charm. The real challenge, though, is to do these things and remain clued into yourself, your actions, and reality, not clueless.
4. Groundhog Day (1993)
Director: Harold Ramis
When Phil Connors (Bill Murray, of Ghostbusters: Frozen Empire), a local weatherman, is sent out to cover the annual emergence of the groundhog, he gets caught in a blizzard that leaves his life turned upside down, trapping him in a time loop where he must relive the same day over and over again.
A sour, narcissistic, self-centered cynic, Phil’s predicament drives him to complete gluttonous distraction, until he realizes how he can turn the situation to his advantage.
Aside from plenty of laughs and its clever storytelling, Groundhog Day is spectacular at delivering witty comedy while exploring themes of personal growth, empathy, and living in the present moment. The movie is also credited with having ushered in mainstream acceptance of comedy films with fantasy-genre elements.
You’ll love the script, which uses witty dialogue and unique situational humor to explore the absurdity of Phil’s predicament. You’ll also love Bill Murray’s clever retorts and transformative performance—specifically the contrast between his character’s internal state and the unchanging state of his external world.
*Side Note: You should also watch this other Bill Murray hit, What About Bob?
5. Jerry Maguire (1996)
Director: Cameron Crowe
One of the most popular movies of the 90s was Jerry Maguire.
Tom Cruise stars as the titular character, a slick sports agent who has a crisis of conscience one day and pens a company-wide mission statement that promptly gets him fired. Desperate to hang on to the athletes he represents, Jerry starts his own management firm with one other employee: single mother Dorothy Boyd (Renée Zellweger, of Bridget Jones: Mad About the Boy), who secretly has a crush on him.
As Maguire loses client after client, he questions his choices until football player Rod Tidwell (Cuba Gooding Jr., of American Horror Story) decides to stick with him. The longer they’re together, the more Jerry and Dorothy begin to fall in love as they struggle to make Tidwell’s deal and their business work.
Jerry Maguire features some clever interplay between characters in their use of sharp, witty dialogue blended with heartfelt emotion amid comedic moments. The characters’ lines are memorable and insightful, often underscoring the absurdity of the situations they find themselves in.
This movie also doesn’t take itself too seriously—a self-awareness that allows for witty observations about the world of sports management and the characters’ personal struggles. It’s all about humor and heart here.
6. Liar Liar (1997)
Director: Tom Shadyac
Say what you will about Jim Carrey’s style of comedy, but he’s one of my favorite actors, and his slew of must-watch witty 90s comedies prove why. With so many under his belt, it’s hard to choose a favorite. While I adore (and can fully recite) Ace Ventura: When Nature Calls, Liar Liar is arguably one of his best films.
Carrey plays conniving, self-centered, hot-shot attorney Fletcher Reede, who’s an ace in the courtroom. However, his dishonesty and devotion to work have ruined his relationships and personal life.
His wife, Audrey (Maura Tierney, of The Iron Claw), has left him for someone more dependable, and Fletcher often breaks his commitments to his young son, Max (Justin Cooper). After Max makes a birthday wish that, for just one day, his dad couldn’t tell a lie, Fletcher finds himself in every lawyer’s worst nightmare.
Only able to speak the truth, he struggles in court on the day he’s set to argue a salacious career-deciding case. That means Fletcher will have to put on his big boy pants and do the right thing in a world where he’s so used to winning by doing what’s wrong.
What makes Liar Liar a must-watch witty comedy is its intelligent use of verbal humor, rapid-fire dialogue, and the impeccable comedic timing of Jim Carrey. His use of wordplay, clever retorts, and energetic delivery amplify the script’s wit, which is layered with comedic brilliance, thanks to the film’s juxtaposition of lies and truth.
7. My Cousin Vinny (1992)
Director: Jonathan Lynn
This is one movie that gets funnier every time I see it. It’s a must-see (and a classic) for fans of witty comedies.
When college-aged New Yorkers Bill Gambini (Ralph Macchio, of Cobra Kai) and Stan Rothenstein (Mitchell Whitfield) set out on a road trip, they’re mistakenly accused of murder in rural Alabama. Alone in a place where New Yorkers are fish out of water, Bill calls the only lawyer he knows: his cousin, Vinny (Joe Pesci, of Bupkis).
Now, Vinny is no criminal lawyer, nor is he a seasoned lawyer. In fact, he’s only ever tried personal injury cases before, and he lost them all. So, when he rolls into court dressed and talking like a mobster, the judge isn’t having it.
It’ll be up to Vinny and his smart but tough-as-nails fiancée, Mona Lisa Vito (Marisa Tomei, of Spider-Man: No Way Home), to successfully navigate this legal battle against a no-nonsense southern judge and local prejudice to prove Bill and Stan’s innocence.
Another one of the most quotable movies of the 90s, My Cousin Vinny’s wit comes from the character interactions, like the wicked, angry banter between Vinny and Mona Lisa, as well as the inventive way Vinny ultimately uses his sharp mind to win the case, despite his inexperience and the cultural differences. His unique courtroom style leads to gut-busting moments and conflicts with the judge that you won’t soon forget.
8. Office Space (1999)
Director: Mike Judge
I’ll be honest: work sucks. Hell, adulting sucks, and that’s exactly what Peter Gibbons (Ron Livingston, of Loudermilk) comes to figure out in Office Space, the must-watch witty 90s comedy that defined a generation of people who hate their jobs, hate being part of a team, hate their boss, and just need to escape from the bullsh*t.
Office Space satirizes the office work life of a typical 90s software company, focusing on a handful of employees worn out by their soul-killing jobs (and as a former day-jobber, I can attest to the soul-killing part).
While undergoing hypnotherapy, Peter is left in a blissful state when his therapist dies in the middle of his session. As a result, he learns to say no to things he doesn’t want to do. He refuses to work overtime, plays games at his desk, and unintentionally charms two consultants into putting him on the management fast-track. When Peter’s friends learn the company is about to downsize, they hatch a revenge plot inspired by Superman III.
Office Space is known for its observational humor about the drudgery and absurdity of office life, using witty dialogue and relatable scenarios to poke fun at corporate culture, annoying bosses, and mundane routines.
9. Swingers (1996)
Director: Doug Liman
In the cult classic hit Swingers, Jon Favreau, of Deadpool & Wolverine, stars as Mike Peters, a New York transplant attempting to acclimate to the Los Angeles way of life but is struggling.
Having recently gotten out of a relationship and a wannabe actor looking to further his comedy career, Mike puts his trust in his best friend, Trent (Vince Vaughn, of Bad Monkey), who is a self-proclaimed master of seduction. Trent takes pride in showing his friend how to make connections and get the attention of women.
As he slowly moves toward regaining his confidence, Mike meets a gorgeous, down-to-earth woman named Lorraine (Heather Graham, of Place of Bones), who gives him the strength he needs to let go of his failed past relationship and embrace what’s right in front of him.
Swingers’ wit stems from its authentic, relatable portrayal of male friendships—particularly the male bond and the unique language developed by its characters. You’ll love the smart, realistic banter between male friends and their attempts to be cool and suave, which, as a chick, you won’t be able to stop giggling at.
10. The Big Lebowski (1998)
Directors: Ethan Coen, Joel Coen
Hands down, The Big Lebowski is the most quotable, must-watch witty comedy of the 90s. Whether you’re a bowler and still do things manually or you’re a golfer and care about nothing, every line in this cult classic gem is memorable.
When Jeff “The Dude” Lebowski (Jeff Bridges) is mistaken for millionaire Jeffrey Lebowski, a.k.a. The Big Lebowski, he’s roughed up, has his head shoved in a toilet, then is made to watch as his precious rug is peed on. It’s the one thing that ties this story together.
So, on a mission to get his rug replaced, The Dude sets out to confront The Big Lebowski, who has a mission of his own. After meeting The Dude, Lebowski decides to task him with being the bagman and delivering ransom money for his allegedly kidnapped young wife.
Both aided and hindered by his friends, Vietnam vet Walter Sobchak (John Goodman, of The Conners) and master of stupidity Donny (Steve Buscemi, of Poker Face), The Dude finds himself in the middle of a messy plot that has none of the things he loves the most: weed, bowling, a White Russian, and his beloved rug.
The Big Lebowski is noted for its eccentric characters, comedic (and creative) dream sequences, and idiosyncratic dialogue. Its unique blend of absurdist humor with memorable characters, distinctive mannerisms, and a laid-back philosophy make it one of the wittiest comedies not just of the 90s but also of the 20th and 21st centuries.
