Entertainment
The 8 Most Fun Movies of the 1990s, Ranked
While the 80s were certainly radical, the 90s were admittedly pretty dang fun. Pop culture bloomed eternal, as music, TV, film, and all art mediums exploded in a cornucopia of diverse directions. While some movies went very dark (Seven, Falling Down, Trainspotting), others took the rollicking, fun-addled themes of the 80s and brought them to new extremes of smile-inducing entertainment.
Here are the eight most fun movies that were released in the 90s, in all their raucous glory. Most of these cinematic gems are pure comedies, but others meld action, drama, and strangeness into the mix. Each one listed here is an immortal entry into the world of movies, and each one is more fun than the next.
8
‘Clueless’ (1995)
The title says it all. The 90s blessed the cinematic world with several films that were updates on literary classics, but none were as funny and joyous as Clueless, the reimagining of Jane Austen’s Emma. Music video star Alicia Silverstone became a household name overnight as the lead in this colorful, jubilant movie that perfectly encapsulates everything that simply is the 90s (and inspired widespread fashion trends galore).
Cher (Silverstone) is a seemingly vapid, obnoxiously wealthy and popular Beverly Hills high schooler with one thing on her mind: match-making. With the help of her bestie, Dionne (Stacey Dash, who has perfect comedic timing), she sets people up left and right (sometimes for her own personal gain, but ostensibly out of “charity”). When the clumsy transfer student Tai (Brittany Murphy, equally grand) arrives, Cher is determined to find her the perfect match. Naturally, things get a tad complicated when Elton (Jeremy Sisto) falls for Cher instead of Cher’s intended target, Tai. From the clothes to the malapropisms, everything in writer-director Amy Heckerling’s Clueless is smart fun (daring you to mock the title).
7
‘Speed’ (1994)
There are a host of 90s action movies that are as fun as they are exhilarating, and none of them embody this duality more than director Jan de Bont’s Speed. With its ultra-fun premise and pitch-perfect casting (can you imagine anyone other than 90s dude Keanu Reeves and America’s sweetheart Sandra Bullock in these roles?), this action-comedy-love story hits all the marks.
The concept is brilliant in its simplicity. If the bus that Annie (Bullock) is driving goes below a certain speed, then the whole thing blows up. Barreling through the busy streets of L.A., the bus is a, well, bomb on wheels. With SWAT team member Jack Traven (Reeves) coaching Annie along the way, a beautiful chemistry is born — along with some of the most entertaining action set pieces of the decade. Throw in a ridiculous villain, Howard Payne (Dennis Hopper, who clearly loved being a lunatic), and you’ve got one of the most fun action movies of all time (just let us never, ever speak of the sequel…).
6
‘Ace Ventura: Pet Detective’ (1994)
While Jim Carrey may have already been in the cultural zeitgeist with the sundry insane characters that he created for the hit sketch comedy show In Living Color (remember, the Wayans Brothers’ weekly program…where J. Lo was a dancer), he didn’t really make it to the mainstream until director Tom Shadyac‘s Ace Ventura: Pet Detective was released. Here Carrey was allowed the freedom to be as zany and rubber-faced as physics would allow, for an entire feature-length runtime.
Ace is a P.I. that specializes in, you guessed it, pet-related cases. When the mascot for the Miami Dolphins, a porpoise with a real purpose, goes missing, Ace is the obvious guy for the job. Carrey is naturally the driving force behind this film, and his performance is sheer, boldly manifested fun. This wacky movie would truly launch Carrey’s career and spawn an equally hilarious sequel. All-righty-then.
5
‘Being John Malkovich’ (1999)
While this film is brilliant for its hilariously bizarre premise alone, and sparks all sorts of existential, philosophical, and metaphysical debates, its overall tone is unabashedly a very fun one. What if you could be someone else? That’s the primary query raised in genius screenwriter Charlie Kaufman’s eccentric script, and the answer is boisterously brought to life by the always fun director Spike Jonze in the masterpiece that is Being John Malkovich.
Craig Shwartz (a bespectacled, pony-tailed John Cusack, boldly playing against type here) is a puppeteer who can’t find work (imagine that). His excessively loving wife, Lotte (a frizzy-haired Cameron Diaz, really playing against type), is just trying to support Craig and feed her one hundred pets. Craig begins working at a weird company on the “7 and a half” floor, where he meets his true love interest (and foil), Maxine Lund (Catherine Keener, at her snarky best). Here they discover a portal that leads directly into the psyche of John Malkovich (playing a perfectly droll version of himself). Obviously, this is a wacky plot line, bubbling with uniquely subverted scenarios, but the film as a whole is one of the smartest, funniest of the 90s, which packs in mysterious, ironic fun into every eccentric scene.
4
‘Happy Gilmore’ (1996)
Current national treasure Adam Sandler was already a movie star (after his memorable SNL run) with his first major movie, Billy Madison (a film, no doubt, that many a Gen X-er and Millennial still quote to this day). This sophomoric classic is, of course, packed to the gills with tremendous amounts of fun sequences and lovably loony characters. However, the viewing public didn’t fully embrace Sandler until director Dennis Dugan’s Happy Gilmore hit the links. This movie is so much fun it should be illegal.
Happy (Sandler, who co-wrote the script) is an “aspiring” professional hockey player; the only caveat is that he can’t really skate. After he hits a fluke golf shot, while attempting to save the home of his grandma (the charming Frances Bay) — a sweet MacGuffin for the ages — Happy realizes that he can make money on the pro golf tour. Sure, whatever. The point is that Sandler is at his furious best here, getting into fights with fans, Bob Barker, and an alligator. The supporting cast of Christopher McDonald (as Shooter), Carl Weathers (as Chubbs), and Julie Bowen (as Virginia) all add to the raunchy fun. All in all, it was even worth the 29 years it took to get a sequel.
3
‘Wayne’s World’ (1992)
Saturday Night Live has produced hundreds of memorable characters over the decades, with many of them receiving their own feature films. Some succeeded, and others flopped — but there is, hands-down, none as fun as director Penelope Spheeris’s Wayne’s World, one of the most quotable 90s movies out there (and that’s saying a lot).
Wayne Campbell (Mike Meyers, in a tie for his best role ever — the other naturally being the titular character in Austin Powers) and Garth Algar (Dana Carvey, whose voice simply cannot be removed from one’s head) run a cable access show from Wayne’s basement. For whatever reason, they are handed the opportunity to go big time, as a powerful exec, Benjamin Oliver (Rob Lowe, at his smarmiest), buys them out. The narcissistic Benjamin naturally has ill-intentions, as he wants to steal Wayne’s love interest, the badass bassist Cassandra (the drop-dead gorgeous Tia Carrere). From head-banging to pranking everyone in their path, Wayne and Garth are two of the most iconic characters to emerge from the 90s, and every scene they’re in bursts with unbridled fun.
2
‘Pulp Fiction’ (1994)
While there were a ton of films that previously incorporated dislocated timelines in cinema history, none resonated with American audiences that much until the arrival of Quentin Tarantino’s big breakout film, Pulp Fiction. The jumping narrative may have been confusing for viewers initially, but mentally putting the timeline into the correct sequence proved to be quite fun indeed for audiences everywhere.
The story is a complex one, with a ton of sub-plots to keep track of, but the basic tale is of a missing suitcase (filled with a mystery material that glows gold) that two hitmen are hired to locate. Of course, the two assassins in question are Vincent Vega (John Travolta, in a role that jump-started his career like no other), and Jules Winnfield (Samuel L. Jackson, who became one of the most beloved character actors ever with this juicy part). One of the more fun side plots involves a disgruntled boxer, Butch Coolidge (Bruce Willis, cool as ever), as he struggles to snag some loot and then evade one of the weirdest basements in film history. The cast features way too many other stellar thespians to name (Uma Thurman, Christopher Walken, and Harvey Keitel, for example), all of whom deliver the goods, and uphold the spirited tone of the movie. While there were quite a few heavy moments in this film (“Zed’s dead, baby, Zed’s dead”), it ultimately is one of the most fun watches in cinema history.
1
‘The Big Lebowski’ (1998)
Film noir has never been this fun. In fact, noir master writer-directors Ethan Coen and Joel Coen had already made quite a few winners in his genre (Blood Simple, Miller’s Crossing), but no one ever dreamed that a noir could be a laugh-out-loud comedy. Everything about this movie is perfect, from the casting to the soundtrack to the surreal, stylishly choreographed bowling sequences. There may be some deep and dark themes explored in this movie, but no quality in it shines as bright as its commitment to providing the audience with unmitigated fun.
The story revolves around “The Dude” (aka, the Duderino, for one), Jeffrey Lebowski (Jeff Bridges), an unemployed, burn-out bowling enthusiast. His rug, which really tied the room together, is mistakenly stolen from his home by a cadre of washed-up German electro bandmates. This was a misunderstanding, as they were really trying to square up a debt with the “Big” Lebowski, a powerful “philanthropist” living in the posh part of town. Eventually, the latter Lebowski hires The Dude to locate his missing trophy wife, Bunny (Tara Reid). The Dude is aided in his quest by Walter Sobchak (John Goodman, who simply is comedy in this movie) and Donny (Steve Buscemi, also amazing, even though he was out of his element). Eventually, The Dude meets the femme fatale, the artist Maude Lebowski (Juliane Moore, whose acerbic, dry wit is merciless). There is an argument to be made that everyone in this cast delivers career-high performances (certainly the most memorable ones for a lot of them). The Big Lebowski has inspired countless group Halloween costumes, bar trivia nights, and the most quotable quotes in film history. It’s possibly the most fun movie ever, but that’s just like, your opinion, man.
The Big Lebowski
- Release Date
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March 6, 1998
- Runtime
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117 minutes
- Director
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Joel Coen
- Writers
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Ethan Coen, Joel Coen
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