15 Most Rewatchable Movies of the 21st Century

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Rewatching a mediocre movie is a chore. If it doesn’t offer anything special, you’ll likely find yourself thinking about a similar film that did it better. But truly great movies are endlessly rewatchable – there’s always something new to notice and appreciate. It’s like you need multiple viewings just to fully savor all the brilliant details. Of course, some truly awful movies are also fun to revisit – think of a cult classic like Plan 9 from Outer Space – but generally, it’s the best films that you’ll find yourself watching over and over again, and they never get old. This is a collection of those exceptional movies – films you can watch five or six times and still enjoy as much as the first time.

We’re focusing on movies from the last 25 years that are highly rewatchable – not necessarily the best movies ever made, but the ones you’ll want to see again and again. Some critically acclaimed films didn’t make the list because they aren’t immediately appealing for repeat viewings, like The Social Network.

15) Toy Story 3

The final act of Toy Story 3 makes the whole movie worth watching again and again. It’s incredibly emotional – many adults were seen crying in theaters! The scene where the toys face potential destruction is heartbreaking, but what follows is a truly beautiful and touching moment of transition. It’s a rollercoaster of feelings.

The movie is intense, but not so much that it would scare young viewers. It gets close to being overwhelming, but ultimately strikes a good balance. That means both kids and adults can enjoy it, finding new layers of meaning with each viewing – especially as adults, if they first saw it when they were younger.

Stream Toy Story 3 on Disney+.

14) Captain America: The First Avenger

As a big fan of the Marvel Cinematic Universe, I’ve always appreciated how a lot of their origin stories really nail that ‘average person gets powers’ trope. They don’t just jump into epic battles; they show us how someone ordinary reacts to suddenly having abilities and how they learn to use them to help people. It’s incredibly relatable and makes those early days of becoming a hero feel really special and personal for each character.

Iron Man’s story began with a battle against people misusing his own company’s technology. Captain America, in his first film, gained superpowers through an experiment and immediately used them to save a friend. These heroes started with personal conflicts that eventually grew into massive, world-saving adventures. It’s appealing to see a hero begin on a smaller scale, tackling a problem they genuinely care about, especially knowing how much bigger their challenges will become.

Stream Captain America: The First Avenger on Disney+.

13) 21 Jump Street (& 22 Jump Street)

The comedies 21 Jump Street and 22 Jump Street, directed by Phil Lord and Chris Miller, are brilliantly funny and showcase the fantastic on-screen connection between Jonah Hill and Channing Tatum. Tatum is a standout in these films. Surprisingly, 21 Jump Street played a key role in helping him be recognized as a genuinely talented actor, especially considering his earlier, more straightforward role in G.I. Joe: The Rise of Cobra. When you’re as funny as Tatum is in these movies, even critics have to acknowledge your skill.

The hilarious dynamic between Hill’s Schmidt and Tatum’s Jenko was still fantastic in 22 Jump Street. The movie cleverly poked fun at the way sequels are often made just to make money, without going overboard. Plus, Wyatt Russell delivered a breakout performance. Overall, 22 Jump Street is just as enjoyable to watch again and again as the first film.

Stream 21 Jump Street and 22 Jump Street on Prime Video.

12) The Harry Potter Saga

Whether or not you’ve read the books, the Harry Potter movies are incredibly engaging. The films create a fully developed and believable world, brought to life by fantastic acting.

These watches are perfect for the holidays, even the ones that aren’t Christmas-themed. Imagine relaxing by the fireplace with family, enjoying a captivating story that everyone, young and old, can truly get lost in. The watch’s immersive and believable world is a big part of its appeal.

Stream the Harry Potter saga on HBO Max.

11) Casino Royale

While 2006 offered several exciting action films, Casino Royale clearly stood out. Many Bond movies are enjoyable to watch again and again – classics like Goldfinger, You Only Live Twice, and GoldenEye come to mind – but Casino Royale is arguably the most rewatchable. It perfectly captures a special, unforgettable quality.

Released just as Mads Mikkelsen was gaining prominence in Hollywood, Casino Royale delivered a thrilling opening sequence with parkour and, crucially, proved that Daniel Craig was a fantastic choice for James Bond. It felt like a revitalizing start to the series, and while Skyfall and No Time to Die are also great films, Casino Royale remains the strongest entry in Daniel Craig’s Bond era, still feeling innovative and exciting today.

Stream Casino Royale on Netflix.

10) Spider-Man (& Spider-Man 2)

Look, if you grew up watching Sam Raimi’s Spider-Man and Spider-Man 2 when you were a kid – like, between eight and thirteen – those movies just hit different. They’re pure nostalgia for me, but honestly, they hold up incredibly well even now because they’re just really good films with some surprisingly deep themes. Spider-Man 3? Yeah, it’s… not great. It gets a bad rap, and while it’s not quite the disaster everyone says, it definitely doesn’t reach the heights of the first two.

Both films are great, but if we had to pick one for rewatching, it would be Spider-Man 2 due to its more complex story. However, the first film features Willem Dafoe in a larger role. It’s a tough choice – we recommend enjoying both again!

Stream Spider-Man and Spider-Man 2 on Disney+.

9) The Lord of the Rings Trilogy

Peter Jackson’s The Hobbit trilogy led some viewers to re-evaluate his The Lord of the Rings trilogy, wondering if it truly lived up to its reputation. Thankfully, despite the shortcomings of The Hobbit films, the original trilogy still holds up as a remarkable achievement.

A well-developed fictional world becomes more and more captivating over time. What makes The Lord of the Rings so special is its ability to draw you in slowly, even after multiple viewings. You rediscover the beauty of Middle-earth and genuinely care about its people, especially when trouble arises. And because the story and performances are so strong, you consistently find yourself rooting for the heroes. Truly great filmmaking remains timeless.

Stream The Lord of the Rings trilogy on HBO Max.

8) Pirates of the Caribbean: The Curse of the Black Pearl

Okay, let me tell you, while the later Pirates of the Caribbean movies don’t get nearly enough credit, nothing compares to the sheer fun of the original, The Curse of the Black Pearl. It really revived the pirate genre, which hadn’t been a sure thing for a while, and turned it into a massive hit with everyone. It’s just pure, energetic entertainment.

The movie offers a great mix of romance, fantasy, comedy, and action. The Curse of the Black Pearl is a truly special film, perfectly cast with actors who were at their peak. Johnny Depp, in particular, gives a legendary performance that’s endlessly entertaining to watch. His dedication to the role makes the movie incredibly enjoyable, again and again.

Stream Pirates of the Caribbean: The Curse of the Black Pearl on Disney+.

7) Old School

Of all the classic college comedies, like Superbad and The Hangover, Old School is the one people keep coming back to. It perfectly captures the silly and often ridiculous experiences of being in college, and surprisingly, it still feels fresh and funny today – unlike some older films like Animal House.

Old School really captured a special comedic moment. It marked a turning point for both Vince Vaughn, who began focusing on comedy, and Will Ferrell, who transitioned from a standout performer on SNL to a leading movie star. Plus, alongside Idiocracy, it perfectly showcased Luke Wilson’s relatable appeal. And let’s not forget the iconic scene of Ferrell getting hit with a tranquilizer dart while Seann William Scott looks on – it’s a moment that never fails to make people laugh.

Stream Old School on Paramount+.

6) The John Wick Films

The first John Wick movie is easy to watch again and again because the story is so simple. It’s a classic revenge tale: a man’s dog and car are taken from him, and he goes to any lengths to get even. You won’t find many more direct plots in an action movie.

This installment not only stands on its own, but also highlights how enjoyable the entire series is to rewatch. The story started simply, but it was developed in a way that keeps you engaged. While the exciting, acrobatic fight scenes are a major draw, it’s the detailed world-building that really makes the series compelling. You could easily watch all four movies (or five, including Ballerina) again and again without feeling like you’ve spent your time poorly.

Stream the first three John Wick movies on HBO Max.

5) Knives Out

It’s rare for a mystery to be enjoyable enough to watch again, but Knives Out pulls it off thanks to Rian Johnson’s clever and entertaining approach to detective work. However, the film’s easygoing nature isn’t the only reason it’s so rewatchable.

What really made the first Knives Out so enjoyable was the cast, especially the connection between Benoit Blanc and Ana de Armas’ character, Marta Cabrera. Daniel Craig and de Armas had great chemistry, which is likely why she was later cast in No Time to Die.

Stream Knives Out on Prime Video.

4) Mad Max: Fury Road

Mad Max: Fury Road is widely considered the most rewatchable action movie of the 2010s. It’s a non-stop thrill ride, grabbing your attention from the beginning with its explosive storytelling, featuring plenty of fuel-powered vehicles and fiery guitar effects.

What makes Mad Max: Fury Road so remarkable is that its intense action is surprisingly easy to follow. However, you really need to watch it several times to fully appreciate how well-crafted it is. You’ll find it’s just as exciting on your seventh viewing as it was when it first came out in 2015.

3) The Dark Knight

While all of Christopher Nolan’s Batman films are worth watching again and again, The Dark Knight stands out as the most rewatchable. It’s a brilliantly made crime film and widely considered the greatest superhero movie ever.

The Dark Knight is brilliantly constructed, with every scene carefully contributing to the overall story. It avoids the pitfalls of its sequel by never feeling pointless or dragging. From the very beginning, the film completely captivates you, and that intense engagement lasts all the way through to the end credits – which is remarkable considering its two-and-a-half-hour runtime.

Stream The Dark Knight on HBO Max.

2) Iron Man

Even before 2008, most people recognized that Robert Downey Jr. was perfectly cast as Tony Stark. He clearly enjoyed playing the role, and that energy was infectious. His witty and sometimes sarcastic portrayal of the character was endearing, which is a testament to his skill as an actor.

Lots of people who aren’t regular Marvel fans have still seen Iron Man, and for good reason – it was a major movie event. Despite facing challenges, it would have easily been the biggest summer blockbuster if it hadn’t been for The Dark Knight. And while it received positive attention, it’s worth remembering how much discussion the infamous refrigerator scene and ending of Indiana Jones and the Kingdom of the Crystal Skull generated – though not always for the right reasons.

Stream Iron Man on Disney+.

1) Step Brothers

Even if you only considered how many memorable lines it has, Step Brothers would be a top pick. A lot of the movie is improvised, which gives the dialogue a natural, energetic feel that makes it really fun to watch again and again, more so than a movie that sticks strictly to the script.

The humor in Step Brothers truly relies on the incredible chemistry between Will Ferrell and John C. Reilly, who clearly loved playing such immature characters. It’s their best film together, even better than Talladega Nights, and a huge improvement over their disastrous attempt at a detective comedy, Holmes & Watson.

Stream Step Brothers on YouTube TV.

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2026-01-28 03:17