Bill Simmons 50 Most Rewatchable Movies of the 21st Century

Are we voting for "Most Rewatchable"?

I know very little about this guy and his opinions, but I think Kill Bill is probably the most rewatchable movie of the 21st Century and it's not even on here

Ah, the Most Rewatchable American Movies of the 21st Century

A list of actually rewatchable movies is like the six Tarantino movies, the four Jackass movies, three or four of the Coen joints, the good comedies that are actually funny instead of just "emotional" Apatowslop (Popstar, Step Brothers, Wet Hot, They Came Together, Naked Gun reboot, Freddy Got Fingered, Pootie Tang, Borat) and a few splatty exploitation joints (Battle Royale, Drive, Ichi the Killer, The Raid, Brawl in Cell Block 99)

The entire premise seems like just a smokescreen to justify middlebrow taste

No Bourne either, did the two shitty later ones color the first three that badly?

Movies on this list I have actually rewatched at least once: Collateral, Lost in Translation, Ocean's 11, Spotlight, Before Sunset, Anchorman, The Devil Wears Prada

Of those, the one I would most happily watch again right now is probably Collateral.

A list of mostly English language movies? Figures.

Have seen:

Lost in Translation (shite)
Get Out (good)
Dark Knight (shite)
No Country For Old Men (great, have rewatched)
Miami Vice (good)
The Departed (don't recall a thng about it)

Plus a Fast flick, maybe 5 or 7? Who knows. Also John Wicks 1 and 3 (in-flight of course), maybe pt. 2 is the artistically credible one though? I may never find out.

Spirited Away would be my #1 pick, having seen it about 10 times.

21st century movie I have rewatched the most is probably Mulholland Drive

Is Bill Simmons a super basic straight man or a super basic gay man?

A list of mostly English language movies? Figures.

― The Luda of Suburbia (Alfred, Lord Sotosyn), Tuesday, December 30, 2025 12:46 PM (twenty minutes ago) bookmarkflaglink

I hate to defend Bill here, but I don't think its an incredibly controversial opinion to think someone's most "rewatchable" movies might be the ones in their native language

Heh, I was listening to this earlier

Super basic bi erasure xxxp

Super basic bi erasure xxxp

― Lady Sovereign (Citizen) (milo z), Tuesday, 30 December 2025 19:03 (sixteen minutes ago) bookmarkflaglink

Yeah I’d have possibly voted for Challengers if it was here.

If nothing else, the episode has me wanting to hate-watch “Limitless”.

No foreign language films, not even any English language films which aren’t American*.

*based on a quick scan of the list.

would vote for no Bill Simmons content ever being posted here, but my rewatcheds from the list (have seen 28 total):

Mean Girls
Get Out
Oceans 11
John Wick 2
Forgetting Sarah Marshall
No Country For Old Men
Fast 5

I’ve seen 23 of these (I have Spotlight on DVD but haven’t fired it up yet)

I don't even know what these are:

Just Go With It
A lot like love
Proof of Life
Hard Ball
Den of Thieves

Hard Ball

i was shocked not to see rounders on here then saw that it was just the 21st century. nobody in the world loves rounders more than bill simmons

movie from the 21st century that I actually rewatch: Mike and Dave Need Wedding Dates

I voted for the most “obviously I would vote for this”, but it easily could’ve been a bunch of other stuff.

Finding Star is Born rewatchable shd be enough to have him committed

the dumbest (xenophobic maybe) take here is that rewatchability can only mean movies in your native language.

and Simmons needs to stop trying to make Den of Thieves a cult classic. it's a horrible movie.

Yeah it's real xenophobic to understand that maybe the basketball podcast man probably wants to kick his feet up and laugh at "I love lamp" for the bazillionth time instead of get enraptured in the sumptous, molasses-paced beauty of Apichatpong Weerasethakul's 'Uncle Boonmee Who Can Recall His Past Lives'

Found on Reddit:

Economy_Towel_315

17h ago
Bill talking Lost in Translation

Billy - “Love when a rewatchable goes abroad. Love Japan here”

Sean - “you think you’ll ever go?”

Billy - “No”

Absolutely amazing that the universe gave this man so much money and zero interest in going anywhere in the world lmao

not all non-US films are just like Weerasethakul's movies, that's stupid.

if you think a guy that has a large influence/platform talking about movies (it's like a regular part of his podcasts, sites) decides to talk about 'comfort' movies and doesn't blink about thinking how this is a list of just US movies and does not think about this during how things are here in the US right now and it's all good, I don't know what to tell you

and it is a bit xenophobic, even if the intention was not! if you were to ask to anyone who doesn't have english as a first language, where the movie is produced has no bearing on how much times they can rewatch it, or being a comfort movie, something good for them.

We're talking about a guy who was born in Massachusetts who writes about basketball

Part of comfort watching is being 90% off book for the movie and bill simmons absolutely does not speak a second language

Part of comfort watching is being 90% off book for the movie and bill simmons absolutely does not speak a second language

Ironically, The Rewatchables is my comfort listening.

All this list represents is a B-list sportswriter deciding his personal taste in movies should be enshrined in the form of a listicle, which is one of the lowest forms of internet content. This is what jaded writers do when they have nothing to say and a space to fill. Thanks for sharing.

The entire premise seems like just a smokescreen to justify middlebrow taste

― Whiney G. Weingarten, Tuesday, December 30, 2025 12:22 PM (eight hours ago) bookmarkflaglink

this is literally what the ringer exists for! which is fine, it's just funny to react to it like it's trying to do anything else.

probably killed him not to put 'the departed' and 'the town' at 1 and 2 simply because they're set in boston

i suppose including 'fever pitch' would have been too obvious even for him

An obvious bias against comic book movies here, but the two Miles Morales movies would make my list.

I do think that the "comfort" movie is a category that gets ignored by film critics. They are movies where you remember a lot of the scenes and enjoy seeing them again. The plot is simple enough that the scenes can be enjoyed by themselves.

comfort movies I have enjoyed watching at least twice:

action trash:
the score
upgrade
crank 1 and 2
ocean's 11 and 12
mission impossible 4-6
casino royale

comedy:
barb & star
walk hard
step brothers
the first 20 minutes of Elf

also mulholland drive, which is a series of amazing scenes.

collateral

anyone who watches a movie in their native language is a cop

2000s movies I have seen more than twice -
Wick 1 & 2
Bourne 1-3
Miami Vice
Collateral
Wendy & Lucy
The Devil’s Rejects

All this list represents is a B-list sportswriter deciding his personal taste in movies should be enshrined in the form of a listicle, which is one of the lowest forms of internet content. This is what jaded writers do when they have nothing to say and a space to fill. Thanks for sharing.

can you post a link to the listicle he wrote?

i just rewatched Neighbors since i saw it theaters and shocked it didn't make the cut over a lot of this. honestly surprised he didn't include The Wolf of Wall Street.

best rewatch "oh this is on streaming" for this time period is The Beach Bum.

i hope this thread ends up:

1. trash bill simmons
2. discuss movies you enjoy rewatching

Genuinely baffled at some on the list here - The Departed? Really?

Hangover or Dark Knight were the only things I would just casually enjoy watching again if it was on in the background somewhere

But agree with Tarantino - any of his would beat this entire list combined

think the only other one here i've seen multiple times is no country for old men and that one loses handily to true grit in rewatchability/comfort-movie-ness. weird pick for this particular framing out of all the coens options

i was listening to this episode today - i thought it was funny that
a) he sprung it on CR & Fennessy unannounced
b) his ranking is arbitrary aside from (i think?) amount of times watched
c) most of these it seems like he watches w his wife and kids hence the bajillion normcore comedies
d) half the list is movies he’s never covered on the show! lmao

its all v dumb and v Simmons & quite funny to me

anyway i voted Miracle

The recent Big Picture “Robert Redford Hall of Fame” with Tracy Letts was fun in a similar way, just half made-up on the spot and everyone pitching in the ones they’d seen. Good parasocial hangout while I took a giant Newfie on a long walk.

the randomly-placed Fast/Furious movies were v funny too

2000s Tarantino are too long for comfort watching, Death Proof aside. (too long period)

Surprised that my pick - mentioned in comfort movies - is missing: Chef.

Given Moneyball and The Social Network, I'm surprised that The Big Short, and Interstellar don't make it. They all feel kind of like latter day basic cable staples ala Rounders and Shawshank, they're always available on streaming somehow and there are a million clips on Youtube when someone needs a quick hit of Anthony Bourdain explaining mortgage-backed securities.

OK, here is my list of 21st century rewatchables though I haven't actually rewatched them all

All the Tarantino Joints Because They Are Honestly Just Pastiches of The Most Eminently Rewatchable Moments From Classic Exploitation Movies
1. Kill Bill: The Whole Bloody Affair
2. Grindhouse
3. Inglorious Basterds
4. Django Unchained
5. The Hateful Eight
6. Once Upon a Time in Hollywood

Coen Brothers Westerns and Musicals (Minus True Grit and plus Burn After Reading)
7. O Brother Where Art Thou?
8. No Country for Old Men
9. The Ballad of Buster Scruggs
10. Burn After Reading

Comedies That are Actually Legit Funny and Not Just a Bunch of Emotionally Stunted Manchild Apatowslop
11. Popstar: Never Stop Never Stopping
12. Step Brothers
13. Wet Hot American Summer
14. They Came Together
15. The Naked Gun 2025
16. Freddy Got Fingered
17. Borat
18. Tropic Thunder
19. Team America: World Police
20. Idiocracy
21. MacGruber
22. Jackass
23. Jackass 2
24. Jackass 3
25. Jackass 4

Modern Exploitation Films
26. Drive
27. Battle Royale
28. Ichi the Killer
29. The Raid
30. Brawl in Cell Block 99
31. The Host
32. Shaun of the Dead
33. Mandy
34. One Cut of the Dead
35. Tokyo Gore Police
36. John Wick
37. John Wick 2
38. John Wick 3
39. RRR

A Few Middle-Brow Classics As a Treat, No Idea Why They Didn't Make Simmons' List
40. Wall-E
41. There Will Be Blood
42. Zodiac
43. 25th Hour
44. Mulholland Drive
45. The Life Aquatic with Steve Zissou

Mostly Impenetrable Experimental Arthouse Shit to Throw on for ~~The Vibes~~
46. Russian Ark
47. Goodbye Dragon Inn
48. Decasia: The State of Decay
49. Twin Peaks: The Return

Pootie Done Did it Again
50. Pootie Tang

think he had a one film per director limit

Pretty dumb arbitrary rule if you're judging things based on the already fairly arbitrary metric of how entertaining they are on repeat viewings

simmons silliness aside, i’ll try to engage somewhat seriously with the question. i was a teenager when most of these came out so i love and have rewatched a lot of these movies. so i’ll just go with the one I rewatched most recently which is ocean’s 11

Coen Brothers Westerns and Musicals (Minus True Grit and plus Burn After Reading)

insane. O Brother is clearly the most rewatchable of their C21, and Hail Caesar likely to creep up as the decades go by

(if "rewatch in parts on cable" was a thing, I bet We Ain't Got Dames would be the pivot point for tens of thousands of individual views)

50 Most Rewatchable Films Of The 21st Century, no anglos allowed

A Prophet
The Good, The Bad & The Weird
JCVD
Mad Detective
Astropia
Yamadonga
Le Prestige de la Mort
Fearless
The Mission
Godzilla: Final Wars
Kamikaze Girls
Oldboy
Infernal Affairs
The Cat Returns
Laissez-Paisser
Time & Tide
Technoboss
Things To Come
Detective Byomkesh Bakshy
Queen
Juan Of The Dead
Le Havre
Don't Go Breaking My Heart
Who Killed Captain Alex?
The Secret Agent
Victory
The Other Way Around
Twilight Of The Warriors: Walled In
The Roundup: Punishment
Merry Christmas
Out Of Season
Rocky Aur Rani
Fallen Leaves
Single8
Mondays
Decision To Leave
RRR
Girl Picture
Humidity Alert
Riders Of Justice
Lost Bullet
Beyond The Infinite Two Minutes
Vengeance Is Mine: All Others Pay Cash
Wheel Of Fortune And Fantasy
Gangubai Kathiawadi
Kaithi
O Filme Do Bruno Aleixo
Masquerade Hotel
Punk Samurai
Mutant Blast

Mix of action crowd pleasers, romcoms, straight comedies and a few more playful, artsier choices that are nonetheless easy to throw on and not abrasive/challenging. Main challenge here tbh was not just listing 50 Johnnie To movies.

I don't think its an incredibly controversial opinion to think someone's most "rewatchable" movies might be the ones in their native language

Not the case for the vast majority of people! We all rewatch English language movies.

We're talking about a guy who was born in Massachusetts who writes about basketball

― Whiney G. Weingarten, Tuesday, 30 December 2025 bookmarkflaglink

Which is why he should be executed by firing squad, don't know what's so hard to understand here

"OK, here is my list of 21st century rewatchables though I haven't actually rewatched them all"

Can someone ask AI to knock off one of these? I know we are all mourning Bardot but it must be worth killing off a species or two.

22. Jackass
23. Jackass 2
24. Jackass 3
25. Jackass 4

jfc

I'll give the guy credit for employing a bunch of good magazine writers and giving 'em somewhere to do their thing well in the wake of Buzzfeed et al ten years ago… I guess he must have met and buddied up to Klosterman, who then proceeded to get him to hire a lot of his pals, and the result was Grantland, which surely only the terminally smug and sneeringly jealous could besmirch…

But goddamn does he seem basic… he has his name on the Music Box series of music docs on Max, and the other night I watched the Counting Crows one, and not only felt hot unswerving hatred mount when "Mr, Jones" and "Round here" unspooled, but also when Duritz opened his mouth and said anything at all … I bet you Simmons really got behind a doc lauding Counting Crows… Harvilla, who works for Simmons, dutifully attests to the band's value, nobody likens Duritz to Ron Jeremy, and the denuoement involves Duritz coming to the realization that the giant tentacles atop his head for an age must be shorn so that his emotional development progresses…

no love for Undercover Brother

Most rewatchable film of the century is The Room.

Whiney is otm re the Jackass movies … dare I say the most otm he has ever been (j/k)

If you can't laugh at a man chugging horse semen, what can you laugh at

listen

Automatic thread bump. This poll is closing tomorrow.

Coinflipped between two films starring multiple abusive creeps that end with an implausible setpiece.

are there actually people here that don't think a Criterion Jackass boxset will not be on the horizon?

#16, limitless

are there actually people here that don't think a Criterion Jackass boxset will not be on the horizon?

I can’t say I don’t think it won’t not be.

can't never not say never!

from this list, I dig rewatching Sicario, Mean Girls, Wedding Crashers, Moneyball, No Country, Superbad, Step Brothers, This is the End, and Anchorman, but I chose The Town because even my wife makes fun of how often I rewatch it, plus it's the subject of possibly the greatest of all of Simmons' Rewatchables podcasts.

I'd have included Forgetting Sarah Marshall on this list a couple of years ago but I don't think there's any way I can ever enjoyably rewatch something with Russell Brand in it.

The entire premise seems like just a smokescreen to justify middlebrow taste

― Whiney G. Weingarten, Tuesday, December 30, 2025 12:22 PM (one week ago) bookmarkflaglink

1000% otm

The entire premise seems like just a smokescreen to justify middlebrow taste

new ilm board description

From Simmons' list, movies I have seen. Asterisk indicates that I have actually watched them more than once.

41 - Sicario
39 - Mean Girls*
38 - Man On Fire
36 - Lost in Translation*
35 - Garden State
30 - Get Out*
27 - Dark Knight*
23 - John Wick 2
22 - Gone Girl
19 - No Country For Old Men*
18 - Bridesmaids
17 - This Is The End*
12 - Old School
10 - Step Brothers
6 - Miami Vice
5 - The Departed
1 - The Devil Wears Prada

As far as the poll, I'm torn between Mean Girls, No Country for Old Men, and This Is the End. No Country being my favorite movie of the three, but for me, I think rewatchability requires something lighter.

Will cobble together my own list of 21st century rewatchables later on.

michael mann movies are genuinely rewatchable, lots of textual depth, great compositions/colors and formal choices, so heterosexual they're gay, etc.

garden state is not a rewatchable movie unless you're a narcissist

I think rewatchability requires something lighter.

Scratch that, because I just thought of some other dark movies I love to rewatch, but they do require getting into the right mindset in a way that's not like "hey, I'll throw this on while I fold laundry" or whatever.

Automatic thread bump. This poll's results are now in.

the universe has been telling me to watch Stepbrothers.

The new Rewatchables Q&A episode opens with a long chat about how a "rewatchable" has changed in the past decade, from something you would watch a segment of when channel surfing to a movie in a streaming library that you'd deliberately choose to revisit.

garden state is not a rewatchable movie unless you're a narcissist

The headphone scene is rewatchable for as many times as you can find new funny songs to play over it.

*Listens to the Thrills once*

*Becomes millionaire*

*Listens to the Thrills TWICE....*

(!?!?!?!)

Ive seen The Wolf Of Wall Street about 4 times now so I'll pick that one

i keep thinking i'll rewatch that, but i'm not sure it'll stand up on a second viewing.

Ah shit, I didn't realize that the poll was closing yesterday. I would have gone for This Is The End.

The following is my list of rewatchables. It doesn't include anything already mentioned in Simmons' list above. Also ignoring the "one movie per director" thing. My criteria is that I need to have rewatched it multiple times and would continue to do so. For example, I've seen Kill Bill or Inglourious Basterds several times, but I've probably had my fill of those so they are not included. My list is a little limited in that most of the movie-watching I've done in my life has been since the pandemic. There are plenty of movies made this century that are new favorites, but haven't slipped back into the rotation yet. My watching habits in the past 5 years have tended towards watching previously unseen movies.

A Mighty Wind
Best in Show
Bottoms
Burn After Reading
Cabin in the Woods
Donnie Darko
Happy Death Day
Happy Death Day 2 U
Hundreds of Beavers
Intolerable Cruelty
Lord of the Rings: Fellowship of the Ring
Lord of the Rings: Return of the King
Lord of the Rings: The Two Towers
Mad Max Fury Road
Mullholland Drive
Rat Race
Shaun of the Dead
Smiley Face
Spirited Away
Trick R Treat
Wet Hot American Summer
Winter’s Bone
X
Zodiac

An ILX Rewatchables poll would be cool

Trying to remember all the early 2000s IFC rewatchables:
High Art
Basquiat
Vincent & Theo
Love and Other Catastrophes
Kicking & Screaming

guy whose most-rewatched film is satantango

I just watched it for the first time recently! I could def watch it again... just not any time soon.

I voted for Ocean’s 11, because I gotta be me

great pick, that’s another def rewatch fave of mine

My #1 has got to be "In the Loop" - I know every joke/insult by heart and still laugh uncontrollably ("SHUT IT, LOVE ACTUALLY!" "Difficult...difficult, lemon, difficult")
#2 is probably "The Room".
#3 is probably "Ghost World".