The 6 Most Fun Movies Released Since 1990, Ranked

Image via Sony Pictures Releasing Published Sep 19, 2026, 4:04 PM EDT Sign in to your Collider account 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) Image via Warner Bros. 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) Image via Sony Pictures Releasing 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. Collider Exclusive · 8 Questions · 2 Minutes Which MCU Character Is Your Best Friend? Steve Rogers · Tony Stark · Peter Parker · Shuri Pick where you meet, what they text you at two in the morning, what they hand you on your birthday and what the two of you keep arguing about. Four very different people are waiting on the other side: the one who never leaves, the one who is exhausting and worth it, the one who replies in four seconds flat, and the one who will roast you and then fix your life. 🛡️Steve Rogers(Captain America) 🛠️Tony Stark(Iron Man) 🕸️Peter Parker(Spider-Man) 🐆Shuri(Black Panther) FIND YOUR FRIEND → 01 Where do the two of you meet? Nobody in this universe makes a friend somewhere normal. AIn a gym at six in the morning, where the two of you are the only people awake. BAt a party you were not really invited to, where they talked to you for an hour. CQueuing for coffee in Queens while something loud happens six blocks away. DIn a lab you had no clearance for, and they decided to let you stay. NEXT QUESTION → 02 Your phone lights up at two in the morning. What does it say? You find out what kind of friend somebody is by what they send at that hour. ANothing at all, because they are already outside, having heard you had a rough week. BFour hundred words about an idea they just had, plus a schematic you cannot read. CAn apology for texting so late, followed by a question that could have waited. DA meme aimed directly at you, sent with no context and absolutely no mercy. NEXT QUESTION → 03 It is your birthday. What do they hand you? The present is never really about the present. ASomething small they made themselves, handed over slightly awkwardly. BSomething absurd and expensive that fixes a problem you mentioned once, months ago. CA gift that clearly took months of saving, wrapped badly, with a long note inside. DAn upgrade to something you already owned, installed without asking you first. NEXT QUESTION → 04 What does a good Saturday with them actually look like? Superheroes have days off, and this is how they spend them. AA long walk, an old diner and a conversation you had both been avoiding. BWhatever they decide at noon, which somehow ends with you in another country. CBad takeaway and an old film on their couch, interrupted about eleven times. DTwo hours in a workshop, arguing about whether your idea would even work. NEXT QUESTION → 05 You have your worst day in years. What do they do about it? This is the part of a friendship nobody puts in the trailer. AThey sit next to you and say almost nothing until you are ready to talk. BThey throw money, noise and three terrible plans at it until one of them helps. CThey turn up with food, refuse to leave, and then check on you every day for a month. DThey tell you the honest version of it, which nobody else was willing to say. NEXT QUESTION → 06 Every real friendship has one fight it keeps having. What is yours? The thing you argue about is usually the thing you like most about them. AThey take risks with their own life that they would never let me take with mine. BThey vanish into work for weeks and expect me to be completely fine about it. CThey keep apologising for things that were never even slightly their fault. DThey are three steps ahead of me and do not always bother explaining why. NEXT QUESTION → 07 The alarm goes off and you are both in the field. What is your job? You get one role on the team, and it says a lot about who you want next to you. AHolding the front line so that everybody behind me gets out of the building. BDoing the thing nobody has a plan for yet, at speed, and inventing the rest. CGetting people off the street quietly before anyone realises we were there. DRunning everything from a screen and talking the rest of them through it. NEXT QUESTION → 08 Ten years on, what do you want this friendship to be? Eight questions in, this is the one that decides who picks up the phone. AExactly the same, because some people are simply permanent and that is the appeal. BLoud and complicated and worth every bit of the trouble it caused along the way. CStill the person I look out for, and still the first one who checks on me. DTwo people who keep each other sharp and never once get sentimental about it. REVEAL MY BEST FRIEND → The Line Is Ringing Your Best Friend Is…Four people, four completely different ideas of what it means to have somebody in your corner. Here is who picked up, what they would ask of you, and what you would get back. Steve RogersYou want the friend who does not leave. Steve is the one who turns up at the door without being asked, who remembers what you said you were worried about, and who has never once made you audition for his attention. His entire character is built on a single sentence, which is that he will not abandon somebody just because it has become expensive to keep them. He is far funnier than people give him credit for, and the joke is almost always at his own expense rather than yours. The friendship comes with a cost, since being close to Steve means being dragged into fights that were never yours and being glad about it later. You would get a friend who tells you the hard thing to your face and then defends you to everybody else in the room. Tony StarkYou want the friend who is genuinely exhausting and completely worth it. Tony will forget your birthday, then build you something at four in the morning that you did not know you needed, and hand it over as though it were nothing. He is bad at saying the warm thing out loud, so he says it in hardware instead, which is why everybody around him ends up with upgraded everything. Being his friend means putting up with the disappearing, the deflecting and the jokes that arrive about ninety seconds too early. What you get in return is somebody who will spend an unreasonable amount of money and effort on a problem the moment it becomes yours. He is the loudest person in the room and the one most likely to be quietly panicking about all of you. Peter ParkerYou want the friend who replies in four seconds and apologises for it. Peter is earnest in a way that is almost unfashionable, and he will take on far more than he can carry rather than admit that he is struggling. He is the only one on this list who needs looking after as much as he looks after you, and that balance is exactly what makes it a real friendship. Nobody in the MCU is better at the small stuff, from remembering the thing you were nervous about to showing up with food you did not ask for. Spider-Man: Brand New Day arrived in July 2026 and put him back where he works best, which is broke, local and carrying the weight on his own. You would get a friend who is sincerely, embarrassingly happy for you when something goes right, with no edge to it at all. ShuriYou want the friend who insults your shoes, fixes your phone and then quietly rearranges your entire life for the better. Shuri does not do soft reassurance, and that is the reason you would believe her when she says you are fine. She is the smartest person in almost any room she walks into and treats that as a reason to tease you rather than a reason to lecture you. The teasing is the affection. When Shuri stops making fun of you, something has gone seriously wrong and you should probably ask her about it. Her story is the one on this list that goes somewhere genuinely dark, which is what turned her from a scene stealer into the emotional centre of the films. You would get a friend who never pities you, never softens the truth, and never once lets you take yourself too seriously. ↻ RETAKE THE QUIZ 4 'Jurassic Park' (1993) Image via Universal Pictures 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) Image via Walt Disney Pictures 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) Image via Warner Bros. Pictures 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) Image via Pixar Animation Studios 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 November 19, 1995 Runtime 81 minutes Cast Tim Allen Buzz Lightyear (voice)