The Rewatchables recently did an episode focused solely on Bill Simmons’ 50 most rewatchable movies from this century, so here at Pop Thruster, I’m shamelessly borrowing the conceit for my own list of the 50 movies I’ve rewatched the most this century.
Note that this doesn’t mean the flat-out best movies here – we’re not looking for award winners necessarily. This is purely about the movies that most compel me to revisit them, again and again.
Also note: the movie year of 2000 was not eligible here if we’re being super nerdy technical about what constitutes the 21st century, which actually knocks a bunch of incredible rewatchable flicks out of the mix.
Anyway, let’s dive in.
1) Adventureland
This is a movie that could have been designed in a lab just for me: it’s a “small story” perfectly executed, it’s talky, it’s often hilarious, and the characters are deeply believable and you really care what happens with them.
It’s also ridiculously stacked with an all-star cast: Jesse Eisenberg, Kristen Stewart, Ryan Reynolds, Martin Starr, Margarita Levieva, Bill Hader, and Kristen Wiig for starters.
2) Sideways
I loved this tale of wine and friendship and love when it first came out in 2004, and love it more deeply now as I’ve aged. I now see it as a spiritual bookend to Swingers, one of my most favorite movies from the ‘90s.
3) Once Upon a Time in Hollywood
A Tarantino masterpiece that I can rewatch endlessly and think about in different ways: the pop culture-drenched late ‘60s, the Hollywood-ness of it all, the alternative history, or simply the opportunity to hang with Leonardo DiCaprio and Brad Pitt and Margot Robbie, all the top of their game.
4) Scott Pilgrim vs. The World
The first half is one of my favorite first halves of any movie I’ve ever seen. The second half is simply very good.
5) Just Friends
Somewhat unfairly maligned as the “Ryan Reynolds in a fat suit” movie, it has become a top romcom rewatch at my house. Endlessly quotable, charming, and legit super funny. Forgiveness is indeed more than saying sorry.
6) Superbad
Ridiculously funny from end to end while also a compelling friendship and coming of age story. What’s not to love?
7) The Wolf of Wall Street
A late career blast of manically fun energy from Martin Scorsese while also a razor sharp skewering of unchecked capitalism run amok. Chef’s kiss great.
8) Palm Springs
Perhaps the best “time loop” movie ever made (and that includes Groundhog Day, the granddaddy of them all), it’s also fun and charming as hell throughout.
9) Vanilla Sky
One of the strangest movies that I still deeply love and enjoy puzzling over. Cameron Crowe’s last great movie to date.
10) Old School
Pure fun and silliness, with Luke Wilson, Will Ferrell, and Vince Vaughn throwing 95 miles an hour. The surrounding cast is packed with eclectically great choices, ranging from Craig Kilborn to Rob Cordry to Artie Lange.
11) Wedding Crashers
We’re going back to back with Vince Vaughn here, this time paired up with the butterscotch stallion himself, Luke’s brother Owen. Incredible supporting roles in this one too from the likes of Isla Fisher, Jane Seymour, Bradley Cooper, and my man Christopher Walken.
12) The Departed
Another Scorsese banger, this time about a corrupt cop (Matt Damon, tremendous as the villain) and undercover cop (DiCaprio, in a restrained and brilliant performance) infiltrating the mob in Boston. Only Jack Nicholson’s bizarro over-the-top performance as the mob boss dings this one slightly.
13) Grandma’s Boy
An unabashedly lowbrow and deeply hilarious crusher, I’m proud to this day that I got my wife to submit to the power of this one.
14) Moonrise Kingdom
My favorite Wes Anderson flick by far, a pure delight.
15) Saving Silverman
One of those movies where you’re happily surprised at how funny and satisfying it is every time you throw it on.
16) Top Gun: Maverick
By far the best big budget action flick of the last 10-15 years.
17) Forgetting Sarah Marshall
Loopy, weird, super funny, dynamite performances, all set against a Hawaiian resort backdrop. Jonah Hill’s “I just went from six to midnight” is one of my favorite throwaway lines of all time.
18) Lone Survivor
The most intense and riveting war movie of this century.
19) Lost in Translation
Bill Murray has never been better as a sad sack actor experiencing a strange interlude in Tokyo with the equally great Scarlett Johansson. Makes me want to get lost in Japan every time I revisit it.
20) Inglorious Basterds
World War II through the prism of Quentin Tarantino at his very best, and it’s wall-to-wall glorious.
21) Gone Girl
A smart and twisty psychological thriller that is prestige-y in all the right ways.
22) The Hangover
This one is now at the point of being an all-time classic comedy.
23) Adaptation
By far my favorite Charlie Kaufman movie, it’s really bizarre, engaging, and very funny.
24) Rock of Ages
My wife and I are both not huge musical comedy fans, and yet we both cry out that this is one vastly underrated musical comedy.
25) The Town
“I need your help. I can’t tell you what it is, you can never ask me about it later, and we’re gonna hurt some people.” That’s all you need to know for this one.
26) Tenacious D and the Pick of Destiny
This flick is criminally underrated, but in my household the legacy of The D is revered.
27) 50 First Dates
Are my wife and I the only people to still say, “Peanut butter cup…” like the one dude from this movie? If so, we’ll proudly own it. In any event, there are few couples in filmic history as charming, cute, and winning as Drew Barrymore and The Sandman.
28) The Irishman
The first time I saw this one (in the theater!), it felt a little long, overwhelming, and even draining. But it gets better and better on rewatch, a masterful elegy and statement from Scorsese that conveys you know what? Crime really doesn’t pay.
29) The Lord of the Rings: The Fellowship of the Ring
Served best over second breakfast (or Elevensies), but works anytime you have three and a half pleasant hours to kill, really.
30) Get Out
Jordan Peele created the genre of creepy prestige horror/satire with this one. Get out of your sunken place and check this one out if you’ve not yet seen it.
31) Dodgeball: A True Underdog Story
Rewards repeated dodge, duck, dip, dive, and dodging.
32) Training Day
My single favorite Denzel Washington performance, so for that reason alone.
33) Snatch
Released in early January, 2001, in the U.S., this one just makes the cut. And good thing too as it’s one of Guy Ritchie’s best ever rollicking British gangster flicks.
34) Clerks II
Clerks is the remarkably hilarious and iconic low budget debut from Kevin Smith, and its 2006 follow up is one of the most surprisingly funny sequels of all time.
35) Shrek
One of the crown jewels in our original DVD collection, this one got lots of time from us in our yeah we can’t really afford cable television days.
36) Harold & Kumar Escape from Guantanamo Bay
While the 2004 stoner comedy original – the seeking of White Castle edition – from John Cho and Kal Penn was arguably a “better” movie, the post-Gitmo exploits are so weird, dumb, and hilarious that it gives it the slight edge in rewatchability. Also: that one redneck lady talking about “going on the online” is one of my favorite rando comedy lines ever.
37) Ex Machina
Like the most elite Black Mirror episodes like “White Christmas” and “Be Right Back,” Ex Machina creeps under your skin and lives there, nearly sentient.
38) Anchorman: The Legend of Ron Burgundy
In any other hands, this movie would be a trainwreck, but with Will Ferrell in his most ideal role and directed by Adam McKay, it becomes stupidly sublime comedy genius.
39) Uncut Gems
The Safdie brothers at their jittery, anxiety-producing peak found their perfect leading man in Adam Sandler’s sweaty, deluded, and beleaguered anti-hero.
40) The Way Way Back
We were holding out for a hero, and man did this one come through. Sam Rockwell rocks well, indeed.
41) The Grand Budapest Hotel
Perfect Wes Anderson vibes that move to the pace of a well-oiled European contraption.
42) Before Sunset
Maybe one of the best endings of any movie ever?
43) The 40-Year-Old Virgin
The one that put Judd Apatow on the mainstream comedy map, I now am most fond of its weirdo side characters and offbeat stuff going on all over the margins of this one.
44) Birdman
I’m endlessly enthralled with both the wild ambition and deeply grounded NYC theater vibes of this one.
45) The Kingdom
A super underrated and genuinely pulse pounding thriller involving American agents going after a Saudi-based terrorist cell.
46) Bridesmaids
One of the flat-out funniest movies of the century to date, and a coming out party for Melissa McCarthy.
47) The Social Network
If for no other reason than an early sequence showcases the real-world problem solving that developing software entails better than any movie I’ve ever seen.
48) Mad Max: Fury Road
Just wall-to-wall bonkers and go-for-it thrilling action entertainment.
49) Whiplash
A “small” story told exceptionally well, with brilliant performances from Miles Teller and J.K. Simmons.
50) Knockaround Guys
I often wish there were more movies around like this one from Brian Koppelman and David Levien: well-made low stakes crime flicks packed with intriguing characters and lots of fun banter.