Movies

15 Most Rewatchable Movies of the 21st Century

There is nothing less rewatchable than an average film. If a movie doesn’t bring anything new to the table you end up thinking of a movie that did what it did, but better, and you pick that better movie. But movies where everything came together? They’re easy to rewatch because there are so many different things to appreciate. It’s almost as if you have to give the movie a couple screenings just to give every perfect aspect the attention it deserves. Now, there are also truly terrible movies out there that are easy to rewatch, e.g. Plan 9 from Outer Space, but for the most part it’s the cream of the crop that finds itself on one’s television repeatedly. What follows are those types of movies, excellent movies that you can watch five or six times and none of its luster is lost.

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However, we’re relegating things to the 21st century. We’re not saying the absolute best movies of the past 25 years, but they are the easiest to take in multiple times. Not all great movies applied, as there are many phenomenal films that don’t necessarily beg for rewatches immediately after the credits are done rolling, e.g. The Social Network.

15) Toy Story 3

image courtesy of walt disney studios motion pictures

Toy Story 3 is rewatchable based on the strength of its third act alone. Seriously, it made adults in the audience sob. First, we think the toys we just spent 2.9 movies getting to know are about to be incinerated then we get the most beautiful passing of the torch scene ever put on the big screen. Your heart ends up bouncing all over the place.

However, the movie isn’t quite emotionally overwhelming enough to alienate children in the audience. It comes close, but not quite. The point is, you can watch and love it as a kid and you can watch and love it as an adult. It’s thematically rich all the way through, and there’s a good chance you’ll get more out of it as an adult than you did in your younger years (provided it came out in your younger years, of course).

Stream Toy Story 3 on Disney+.

14) Captain America: The First Avenger

Chris Evans as Captain America selling war bonds in Captain America: The First Avenger
image courtesy of walt disney studios motion pictures

Several MCU solo debut adventures have done a really great job of capturing an ordinary Joe or Joanne’s seizure of some sort of strength and using it for good. They understood just how moving a hero’s journey could be, and found ways to tailor early crime-fighting days to the particular hero.

For Iron Man it was a fight against those who were using his own company’s weapons. For Captain America in Captain America: The First Avenger it was getting an experimental procedure then using that procedure to rescue someone who he was close to. Those are personal beginnings that led to later big spectacle world saving. It’s endearing to watch a hero start small (compared to what comes later, anyway) with something they feel connected to.

Stream Captain America: The First Avenger on Disney+.

13) 21 Jump Street (& 22 Jump Street)

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The two funniest movies of the 2010s, Phil Lord and Chris Miller’s 21 Jump Street and 22 Jump Street are whip-smart and feature lovable chemistry between Jonah Hill and Channing Tatum. Tatum in particular is a highlight. It can’t be overstated just how integral 21 Jump Street was in, oddly enough, him being seen as a serious actor after his dry work in G.I. Joe: The Rise of Cobra. If you can do comedy as well as he does it here, even your detractors will admit you’re talented.

The chemistry between Hill’s Schmidt and Tatum’s Jenko continued to be strong in 22 Jump Street, which upped the meta nature of the 2012 movie without being overwhelming. In fact, it was pretty incisive commentary on how sequels are cash grabs. Toss in a very charming star-making performance by Wyatt Russell and 22 Jump is just as rewatchable as its predecessor.

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

12) The Harry Potter Saga

Harry Potter and the Prisoner of Azkaban
Image Courtesy of Warner Bros.

Even if someone didn’t read the books, the Harry Potter saga is compulsively watchable. It’s such a well-realized world loaded front to back with note-perfect performances.

These are great holiday season watches, even when it comes to the ones that feature nothing related to Christmas. You can just sit next to a fireplace with your whole family surrounding you and enjoy. It appeals to all ages, due in no small part to the fact that it takes its fantastical world seriously.

Stream the Harry Potter saga on HBO Max.

11) Casino Royale

image courtesy of sony pictures releasing

2006 was a good year for action movies, but Casino Royale was still the easy winner. There are plenty of rewatchable Bond movies, e.g. Goldfinger, You Only Live Twice, and GoldenEye, but there’s a strong argument to be made that Casino Royale is the most rewatchable of them all. It’s just such an example of catching lightning in a bottle.

We get Mads Mikkelsen just before he’s about to become a mainstay in Hollywood. We get free running for an opening action sequence. And, most importantly, we get a controversial choice for 007 absolutely knocking it out of the park. Casino Royale was a breath of fresh air and, while Skyfall and No Time to Die are both excellent entries in the saga, there was no beating Casino as far as Daniel Craig’s run as the superspy. Even today it still feels fresh.

Stream Casino Royale on Netflix.

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

Tobey Maguire as Peter Parker looking at his hands in Spider-Man 2 (2004)
image courtesy of sony pictures releasing

For those who were anywhere between eight and thirteen when Sam Raimi’s Spider-Man and Spider-Man 2 came out, they are the apex of youthful nostalgia. And, because they’re excellent movies with some thematic heft, they’re still extremely watchable today. Spider-Man 3? Ehh, not so much, though it isn’t the disaster it’s oft made out to be.

We’re putting both films here, but if there’s one that is slightly more rewatchable than the other it’s Spider-Man 2 because its narrative is a lot deeper. Then again, the first one has Willem Dafoe in more than a cameo. It’s very hard to choose…just rewatch both.

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

9) The Lord of the Rings Trilogy

image courtesy of new line cinema

Peter Jackson’s own The Hobbit trilogy made some people look back to his The Lord of the Rings trilogy and ask themselves if they were the masterpieces they thought they were. Fortunately, in spite of how mind-numbing The Hobbit movies are, the answer is still yes, his first trilogy is, indeed, a masterwork.

When a world is slowly developed it becomes increasingly engrossing. The miracle of The Lord of the Rings is that you can feel yourself getting pulled into that world gradually even if you’ve watched the whole trilogy five times. You fall in love with the peaceful version of Middle Earth again and again and feel for its inhabitants when things start to go sour. And, when things do go sour, you again and again hope for the protagonists’ success because the writing and acting has done such a great job of endearing them to you. Great filmmaking never really ages.

Stream The Lord of the Rings trilogy on HBO Max.

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

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For the record, its first two sequels are incredibly underrated, but even they don’t hold a candle to just how energetic and purely enjoyable Pirates of the Caribbean: The Curse of the Black Pearl is. This film managed to make pirate films, which were typically pretty risky gambles, into something that appealed to audiences on the macro scale.

We get romance, we get fantasy, we get comedy, and we get action. The Curse of the Black Pearl is a unique cinematic gift that got the exact right actors at the exact right time of their careers. This is especially true of Johnny Depp, who delivers one of the most iconic performances of all time. His devoted work alone is fun to watch over and over.

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

7) Old School

image courtesy of dreamworks pictures

Even more than Superbad and The Hangover, Old School is compulsively rewatchable. It captures the dumbness many of us experienced in our college years. Better yet, it hasn’t aged as poorly as Animal House.

Old School is another example of lightning being caught in a bottle. This was where Vince Vaughn started to move from more serious material to comedic films. It was where Will Ferrell started to move up from SNL scene-stealer to movie star. And, along with Idiocracy, it was the best use of Luke Wilson’s everyman charms. Not to mention, Ferrell getting a tranquilizer dart to the neck as Seann William Scott stares at him in awe will never get old.

Stream Old School on Paramount+.

6) The John Wick Films

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On one hand, the first John Wick movie is rewatchable because its so simplistic. A man had his dog murdered and his car stolen and does all he can to exact vengeance. It’s about as straightforward a plot as an action film can have.

But this entry is also championing the entire franchise as rewatchable. And the reason for that is just how well the initially simple story was built upon. Its key appeal is acrobatic gun-fu fight sequences, but the real attention glue is the world-building. You can binge watch these four movies repeatedly without feeling as though you’ve wasted eight hours (ten if you include Ballerina).

Stream the first three John Wick movies on HBO Max.

5) Knives Out

Ana de Armas as Marta talking on the phone in Knives Out
image courtesy of lionsgate

It’s pretty impressive that a mystery movie is easy to rewatch, but that’s a testament to just how fun and stylish Rian Johnson makes sleuthing in Knives Out. But the breeziness of the mystery is just part of why you can put this one on multiple times.

The real key to the first Knives Out‘s appeal is this particular ensemble. This is particularly true of Benoit Blanc’s chemistry with Ana de Armas’ Marta Cabrera. It’s pretty clear that Craig and de Armas work well together, hence her later popping up in No Time to Die.

Stream Knives Out on Prime Video.

4) Mad Max: Fury Road

image courtesy of warner bros.

The most rewatchable action film of the 2010s, Mad Max: Fury Road is two hours of adrenaline rush. From the very first scene you’re roped into its high-octane form of storytelling, which involves a lot of gasoline and guitars that spurt fire.

The miracle of Fury Road is that the barrage of action sequences are complex, but they’re not hard to follow. Even still, to get a full grasp of just how impressively its action is, it is best to watch it multiple times. In the process you’ll see that it’s just as enthralling during viewing seven as it was in theaters in 2015.

3) The Dark Knight

The Dark Knight poster cropped
Image Courtesy of Warner Bros. Pictures

One might argue that Christopher Nolan’s entire trilogy is rewatchable, but The Dark Knight is still the most rewatchable of the three. It’s a masterclass in crime epic filmmaking, all the while being the best superhero film of all time.

The film really is a bunch of story-furthering puzzle pieces put in exactly the right place. Unlike its sequel there is never a scene that feels either needless or uninvolving. From moment one you are glued to The Dark Knight and that doesn’t dissipate until the credits, which is highly impressive since it’s two and a half hours.

Stream The Dark Knight on HBO Max.

2) Iron Man

Robert Downey Jr. as Tony Stark giving a speech in Iron Man (2008)
Image courtesy of Marvel Studios

Back in 2008, even the people who didn’t really know who Tony Stark was understood from moment one that Robert Downey Jr. was in the role of a lifetime. He was having fun and we were having fun with him. His snarky nature as the character was charming, not off-putting, and that’s a real accomplishment.

There’s a reason that tons of people who didn’t keep up with the MCU still have seen Iron Man. It was something of an event, and deservedly so. It was a film that had a deck stacked against it yet, were it not for The Dark Knight, would have been the most talked-about movie of the summer. In a positive regard, anyway. One can’t forget just how talked about the refrigerator scene and climax of Indiana Jones and the Kingdom of the Crystal Skull were.

Stream Iron Man on Disney+.

1) Step Brothers

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Step Brothers would nab the top spot on quotability alone. It also has a lot of improv fueling it, and when done right improv dialogue lends a product a spontaneity that is more rewatchable than something fully dependent on a script.

But none of Step Brothers would work were it not for the chemistry between Will Ferrell and John C. Reilly, who are both blatantly having a ball playing adult children. This is the apex of their collaborations, serving as a step up from Talladega Nights: The Ballad of Ricky Bobby (and undoubtedly a million times better than the trainwreck that was Holmes & Watson).

Stream Step Brothers on YouTube TV.