The 6 Most Fun Movies Released Since 1990, Ranked
I’ve talked about the most fun movies from the 2000s and then through the 2010s. But now I get to insert the evergreen, highly influential masterpieces and this becomes a complete take. Some movies make you remember the story. These make you remember the feeling of watching them.
Fun is such a serious and diverse compliment here. It’s a wholesome expression. These movies understand anticipation, release, character, rhythm, and the pure pleasure of giving an audience something it desperately wants to see. They can be scary, emotional, strange, or technically groundbreaking. None of that gets in the way of the basic truth. These 6 are the funnest movies released since 1990 and are outrageously easy to love.
6
‘The Matrix’ (1999)
The Matrix starts with Thomas Anderson (Keanu Reeves) living a life that already feels slightly wrong. Then Morpheus (Laurence Fishburne) offers him a red pill, Neo wakes up inside a machine-filled nightmare, and suddenly the dull office worker we met twenty minutes earlier is learning kung fu inside a simulated world.
The joy is in discovery. “There is no spoon” becomes useful advice instead of nonsense. Agents can hijack anyone inside the Matrix. Phones become exits. A lobby shootout turns concrete columns into dust while Neo and Trinity (Carrie-Anne Moss) move like they have rehearsed gravity out of existence. Bullet time became a cultural phenomenon because it looked impossible in 1999, but the movie’s real trick is how quickly the rules become fun to understand. You are learning the world at the same speed Neo is. Every answer opens another door, and almost every door leads somewhere cooler.
5
‘Spider-Man: Into the Spider-Verse’ (2018)
Miles Morales (Shameik Moore) does not become Spider-Man gracefully. He sticks to Gwen Stacy (Hailee Steinfeld)’s hair, panics when his hands stop cooperating, and cannot figure out how to control half his powers. That awkwardness makes Spider-Man: Into the Spider-Verse immediately lovable because Miles feels like a kid trying to survive something much bigger than him before he ever feels like a superhero.
Then Peter B. Parker (Jake Johnson) arrives carrying years of disappointment and pizza weight. Gwen has her own history. Spider-Man Noir (Nicolas Cage) talks like he wandered in from another genre. Spider-Ham (John Mulaney) treats cartoon logic as a legitimate fighting style. The movie can somehow hold all of them without making Miles feel crowded out. His leap from the skyscraper remains the high point because the spectacle means something. He is finally choosing to trust himself. “What’s Up Danger” kicks in, the city seems to fall upward, and for a few seconds superhero cinema feels brand new again. And if it isn’t already clear, this is an animated film.
4
‘Jurassic Park’ (1993)
Jurassic Park does something almost cruelly smart. It makes dinosaurs feel miraculous before it makes them terrifying. Dr. Alan Grant (Sam Neill) sees the brachiosaurus, John Hammond (Richard Attenborough) proudly explains the park, and for a little while you understand why everyone involved believed this was the greatest idea in human history.
Then the power goes out. The T. rex attack comes sliding in. The movie takes time with it. A cup of water trembles. Something heavy approaches. The fence is suddenly useless. Later, velociraptors stalking children through a kitchen turn stainless-steel counters and swinging doors into pure nightmare fuel. Yet the movie never becomes too grim to enjoy. Ian Malcolm (Jeff Goldblum) is still flirting through chaos theory, Hammond is still learning the difference between imagination and control, and Grant is still reluctantly becoming responsible for two kids. Jurassic Park gives you wonder, terror, adventure, and dinosaurs without ever making any of them feel like separate attractions.
3
‘Pirates of the Caribbean: The Curse of the Black Pearl’ (2003)
Jack Sparrow (Johnny Depp) enters Pirates of the Caribbean: The Curse of the Black Pearl standing proudly on a sinking boat and somehow steps onto the dock as though the whole thing happened exactly according to plan. That’s his chill. That entrance tells you everything you need to know. This movie wants danger, ghosts, sword fights, romance, betrayal, and jokes, but it refuses to act impressed with itself.
Elizabeth Swann (Keira Knightley) can negotiate with pirates perfectly well. Will Turner (Orlando Bloom) brings enough sincerity to make Jack’s nonsense even funnier. Barbossa (Geoffrey Rush) treats being cursed like a theatrical profession. Moonlight turns the crew into skeletons, a blacksmith shop becomes a playground for a duel, and the Pirate Code remains important only when somebody finds it convenient. Jack is the wild card holding it all together because you are never completely sure whether he is improvising or already several moves ahead. Either way, following him is ridiculously entertaining.
2
‘Mad Max: Fury Road’ (2015)
There is no polite way to ease into Mad Max: Fury Road because the movie itself has no interest in easing into anything. Furiosa (Charlize Theron) takes the War Rig off course, Immortan Joe (Hugh Keays-Byrne) realizes his wives are gone, engines start roaring, and within minutes an entire army is chasing one truck across the wasteland.
Somehow the chaos never becomes confusing. You understand who is behind, who is gaining, what just broke, and why the next obstacle could kill everyone. War Boys swing on poles between moving vehicles. Nux (Nicholas Hoult) sprays chrome into his mouth and begs to be witnessed. A guitarist strapped to a wall of speakers provides live music with a flamethrower because apparently the apocalypse still respects production value. Max Rockatansky (Tom Hardy) gradually stops trying to escape the group and starts believing in Furiosa’s mission. Then they reach the end of the road and decide the best option is to drive straight back through everything they just survived. That is cinema with absolutely no fear of excess.
1
‘Toy Story’ (1995)
Every kid has wondered what their toys do when nobody is looking. Toy Story takes that thought seriously enough to build an entire social hierarchy around it. Woody (Tom Hanks) has been Andy Davis (John Morris)’s favorite for years. Buzz arrives, takes over the room almost immediately, and does not even realize he is a toy. Woody reacts with the maturity of someone watching a new coworker get promoted on their first day.
That rivalry gives the movie its heartbeat. Buzz genuinely believes he can fly. Woody keeps trying to prove he cannot. Then both end up at Sid Phillips (Erik von Detten)’s house, where childhood imagination suddenly becomes terrifying and the “mutant” toys turn out to be far kinder than they look. Pizza Planet, the claw aliens, the moving truck chase, and Buzz finally learning the truth about himself are all lodged permanently in pop culture. The animation changed movies. The friendship is why people still care. Nearly thirty years later, you can put Toy Story on and the room still belongs to it.
Toy Story
- Release Date
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November 19, 1995
- Runtime
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81 minutes
- Director
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John Lasseter
- Writers
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John Lasseter, Andrew Stanton, Joss Whedon, Alec Sokolow, Joel Cohen, Joe Ranft, Pete Docter
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Tim Allen
Buzz Lightyear (voice)
