20 Movies That Are Probably The Most Rewatchable Of The Century So Far

It’s fair to say that the 21st century has produced some great movies. What’s more, since the turn of the millennium, we’ve witnessed the rise of some exceptional film franchises, enjoyed our fair share of superlative indie flicks and cheered as some of our favorite superheroes took to the big screen for the first time.

But which films of the last two decades really warrant repeat viewing? Well, no need to ponder that question any further: just put one of the following flicks on, sit back and enjoy.

20. Triangle

It may not have had the biggest budget in the world, but unique 2009 thriller Triangle does more than most films with four times as much money behind them. And while the basic premise of the movie is a simple one – a boat trip that goes horrifyingly wrong – that’s just skimming the surface of this multi-layered flick. Indeed, given Triangle’s plot’s temporal loops, alternate timelines and twists and turns around every corner, it’s exactly the sort of feature that requires multiple viewings to really grasp its complex narrative.

19. Zoolander

Few comedic films of the 21st century are as endlessly quotable as the fashion-industry parody Zoolander. Featuring hilarious performances by Ben Stiller, Owen Wilson and Will Ferrell, it’s one of those oh-so-rare comedies that doesn’t wear thin after repeated viewings. Chances are that you’ll be laughing just as hard the tenth time you watch it, in fact.

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18. The Incredibles

On the surface, Brad Bird’s 2004 motion picture The Incredibles is an entertaining and action-packed animation. However, at its core, it’s a touching story about the bond that brings a family together. And whether it’s the incredibly witty dialogue, the stunning visuals or the lovable characters, The Incredibles has so much going for it that you’ll want to enjoy it repeatedly.

17. Guardians of the Galaxy

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Guardians of the Galaxy looked good on paper, not least because its ensemble cast featured the likes of Chris Pratt, Zoe Saldana and Vin Diesel. But who could’ve predicted just how good it would turn out to be? Yes, amid a sea of movies adapted from comic books, the 2014 superhero blockbuster easily stands out as one of the best of its kind. Indeed, Guardians’ visceral set-pieces and surprisingly hilarious script will keep you rooting for its space-bound misfits again and again.

16. Harry Potter and the Philosopher’s Stone

Even though Harry Potter and the Philosopher’s Stone is probably not the best entry in the franchise, the 2001 fantasy is rewatchable for one very important reason: it’s the one that started it all. Yes, fans of the Harry Potter series certainly remember where they were when this magical flick came out, and it’s fair to say that they love looking back to the origins of the books’ first movie adaptation.

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15. District 9

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Who says that blockbusters can’t be thought-provoking as well as action-packed? Well, 2009’s District 9 proved that both can sit side by side, not least through its imaginative plot that draws on the racial tensions and discriminatory segregation of apartheid-era South Africa. And while the hideous transformation of lead character Wikus is enough to make your skin crawl, his evolving relationship with the alien Christopher is definitely enough to also bring a tear to your eye. There’s so much going on, in fact, that you’ll need to see the Neill Blomkamp-directed sci-fi more than once to fully appreciate it.

14. Shutter Island

Although he’s mostly known for his stylish crime flicks, director Martin Scorsese turned his attention to the horror-thriller genre for 2010’s Shutter Island. The movie follows two U.S. Marshals who have been sent to an isolated insane asylum to investigate the disappearance of one of the facility’s patients. But, as you may already know, all is not what it seems on the island. Shutter Island’s watchability, meanwhile, comes from its clever use of suspense and intrigue – and that plot twist at the end is sure to have you coming back to join the dots up.

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13. Donnie Darko

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Speaking of joining the dots up, few movies of the current century have encouraged as much fevered speculation as Donnie Darko. Indeed, the 2001 psychological sci-fi has been dissected and theorized about for years now, with fans drawing up their own conclusions of what exactly it all means. In short, it follows the life of a lonely suburban teenager who keeps having visions of a giant rabbit figure called Frank. And with its steady stream of plot strands, peculiar cast of characters and constant flirtations with avant-garde storytelling, Donnie Darko basically demands repeated viewings so that you can finally unravel it.

12. The Avengers

When it comes to Hollywood blockbusters, they don’t get much better than The Avengers. After all, it’s a great movie from a critical standpoint as well as being a box office smash. And since its release in 2012, the film has dazzled audiences with its special effects, dropped jaws with its action and sent fanboys into a frenzy with its connections to the comic. Sure, it’s another big-budget superhero flick – but when it’s this endlessly entertaining, who cares?

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11. Almost Famous

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Based around an aspiring young music writer, Cameron Crowe’s 2000 semi-autobiographical movie Almost Famous is clearly the work of someone with intimate knowledge of the topic. It follows the highs and lows of lead character William Miller’s pursuit into journalism in the 1970s, with some star-studded performances provided by Kate Hudson and the late, great Philip Seymour Hoffman scattered in along the way. Make no mistake about it: Almost Famous is an enjoyable journey that you’ll want to go on multiple times.

10. Mad Max: Fury Road

Sometimes you just need something that doesn’t require too much thought while still providing plenty of eye candy, and Mad Max: Fury Road delivers in spades on both fronts. Starring Tom Hardy and Charlize Theron, the no-nonsense blood pumper is loaded with explosive moments, bombastic fight sequences and unreal chase scenes – exactly what you’d want from a blockbuster action flick. It’s high-octane stuff – and so certainly the kind of mindless entertainment that you’ll want to absorb more than once.

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9. Pirates of the Caribbean: The Curse of the Black Pearl

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Don’t let its sequels put you off: Pirates of the Caribbean: The Curse of the Black Pearl is one hell of a ride. For one, it finds Johnny Depp in inspired form, rattling off his slurred lines like he showed up on set intoxicated. However, it’s not just Depp’s performance that makes The Curse of the Black Pearl so entertaining, but the movie as a whole. Laughs, romance, action and pretty much everything else all come together to make this swashbuckling adventure one you’ll want to revisit on a frequent basis.

8. Anchorman

Although Will Ferrell had previously shown moments of brilliance, he didn’t truly come into his own until the laugh-out-loud funny Anchorman was made. Playing the role of television anchor Ron Burgundy, Ferrell delivers some of the most memorable lines in any comedy movie this side of the 21st century. And whether you’re particularly fond of Burgundy trying to woo his female co-host or the moment when he and his co-workers take on the other news station anchors, you’ll still find Anchorman endlessly funny and endlessly rewatchable.

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7. The Dark Knight

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Nothing could prepare audiences for the tour de force in filmmaking that is The Dark Knight. And of course, its crowning glory is Heath Ledger’s twisted portrayal of The Joker – a performance so villainous it is still to be topped in the 21st century. Plus, the reasons for rewatching this modern classic are endless; it could be to see the inner turmoil that Batman struggles with throughout the movie, for example, or just simply to witness the many mischievously subtle mannerisms of The Joker. Either way, you’ll watch it again and again and still find something new to love about it.

6. Gladiator

When you consider films that tick all the boxes, you’d be remiss not to consider Gladiator. The epic historical piece from 2000 follows the story of Maximus Decimus Meridius on his quest to avenge the deaths of his family – a quest that ultimately results in some brutal coliseum battles. What really takes this emotive picture to another level, though, is the acting. Indeed, Joaquin Phoenix, Oliver Reed and Richard Harris turn in highlight-reel performances throughout, effectively giving Gladiator a believability usually lacking in blockbusters these days.

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5. Skyfall

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After the flawed Quantum of Solace, the James Bond franchise arguably found itself floundering somewhat towards the end of the noughties. However, in true 007 style, the movie series came back with a bang in 2012 with the stunning Skyfall. Commonly cited as one of the best in the Bond canon, Skyfall finds the suave protagonist at his finest, with a truly memorable villain in Javier Bardem’s Raoul Silva thrown in for good measure. Much like the main man himself, Skyfall is equal measures sleek, sophisticated and confident.

4. Shrek

Animated movies began to stagnate as the ’90s closed out, with them frequently lacking the lovability or character that, say, Toy Story had. However, that all changed in 2001, because there was a new kid (or, rather, ogre) in town: Shrek. In fact, the first screen outing for the eponymous green misfit captivated audiences, thanks in part to fantastic voiceovers by Mike Myers, Eddie Murphy and John Lithgow. What’s more, Shrek just gets better and better with repeated viewings.

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3. Memento

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Fans of Memento will tell you that you need to see it a few times before you start to understand it – and they’re right. In true Christopher Nolan fashion, the jigsaw-puzzle thriller is rather like an onion with its multiple layers, in fact. And as the movie is based around a lead character with amnesia, the story becomes a real psychological test of the viewer as well. What’s real? What’s fake? These are all questions you’ll be asking yourself as this nail-biting piece of cinema plays out to its jaw-dropping conclusion.

2. The Lord of the Rings: The Fellowship of the Ring

Has there been a more captivating film released in the 21st century than Peter Jackson-directed The Fellowship of the Ring? If so, we’re yet to find it. Indeed, it whisks the viewer away to another place altogether for almost three hours – yet it feels like only half that time has been spent in front of the screen. And while the sequels were good, they definitely can’t touch their magical predecessor in terms of scope, imagination and that special sense of wonderment.

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1. Inception

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Both The Dark Knight and Memento are great movies, but perhaps director Christopher Nolan’s crowning achievement is the mind-bending masterpiece Inception. In fact, no movie of the current century can claim to have the same ambition, the same scope or the same fluidity. Its story centers on Dom Cobb (played by Leonardo DiCaprio), who has been tasked with planting a dream into the head of his employer’s rival. However, that’s really just a precursor to what’s about to transpire. And as the movie practically makes up its own rules with regards to dreams, totems and interactions, you’ll have to watch it at least a few times to fully get the gist of it. Thankfully, though, Inception improves with every viewing.

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