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Bill Simmons Top 50 Most Rewatchable movies of the 21st Century

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:18:13

New @TheRewatchables — The 50 Most Rewatchable Movies of the 21st Century …. with me, @ChrisRyan77 @SeanFennessey
Important note: This was MY list. Counted down from 50 to 1 for CR and Sean.
(Controversy ensued.)https://t.co/EZAyfJDHko
— Bill Simmons (@BillSimmons) December 30, 2025

Bill Simmons sucks*

Posted by bjl63 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=bjl63' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 21:05:11, in reply to "Bill Simmons Top 50 Most Rewatchable movies of the 21st Century"

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New @TheRewatchables — The 50 Most Rewatchable Movies of the 21st Century …. with me, @ChrisRyan77 @SeanFennessey Important note: This was MY list. Counted down from 50 to 1 for CR and Sean. (Controversy ensued.) https://t.co/EZAyfJDHko — Bill Simmons (@BillSimmons) December 30, 2025 .

Yet I still listen to him*

Posted by apusikam <iframe src='https://mb.boardhost.com/TheDeuce/info/user=apusikam' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 21:16:09, in reply to "Bill Simmons sucks*"

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I've been a fan of his writing since the beginning, but his voice is so grating*

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on January 1, 2026, 1:11:26, in reply to "Yet I still listen to him*"

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I despise his writing. Dude needs an editor*

Posted by bjl63 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=bjl63' width='330' height='300' border=0 style='border:none;'> on January 1, 2026, 8:57:04, in reply to "I've been a fan of his writing since the beginning, but his voice is so grating*"

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Should really be called his top fifty rewatched movies*

Posted by bulldogmba <iframe src='https://mb.boardhost.com/TheDeuce/info/user=bulldogmba' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 20:57:46, in reply to "Bill Simmons Top 50 Most Rewatchable movies of the 21st Century"

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It’s literally what it is. *

Posted by digs <iframe src='https://mb.boardhost.com/TheDeuce/info/user=digs' width='330' height='300' border=0 style='border:none;'> on January 1, 2026, 0:19:49, in reply to "Should really be called his top fifty rewatched movies*"

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the list...

Posted by Orangeillini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Orangeillini' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:24:27, in reply to "Bill Simmons Top 50 Most Rewatchable movies of the 21st Century"

50 - Just Go With It
49 - A lot like love
48 - Knocked Up
47 - Flight
46 - The Equalizer
45 - Miracle
44 - Borat
43 - Wedding Crashers
42 - Wolf of Wall Street
41 - Sicario
40 - Collateral
39 - Mean Girls
38 - Man On Fire
37 - Top Gun Maverick
36 - Lost in Translation
35 - Garden State
34 - Black Hat
33 - Proof of Life
32 - A Star Is Born
31 - Funny People
30 - Get Out
29 - Hard Ball
28 - Moneyball
27 - Dark Knight
26 - Oceans 11
25 - Creed
24 - Fast 7
23 - John Wick 2
22 - Gone Girl
21 - Forgetting Sarah Marshall
20 - Den of Thieves
19 - No Country For Old Men
18 - Bridesmaids
17 - This Is The End
16 - Limitless
15 - Sideways
14 - Spotlight
13 - Before Sunset
12 - Old School
11 - Fast 5
10 - Step Brothers
9 - Taken
8 - Superbad
7 - Hangover
6 - Miami Vice
5 - The Departed
4 - The Town
3 - Anchorman
2 - The Social Network
1 - The Devil Wears Prada

1) taken 2) John wick - that’s the top 2. Tons of action, minimal dialogue, likable main charactr*

Posted by MC <iframe src='https://mb.boardhost.com/TheDeuce/info/user=MC' width='330' height='300' border=0 style='border:none;'> on January 1, 2026, 13:55:56, in reply to "the list..."

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Hello, is this President Clinton? Good! I figured if anyone knew where to get some Tang, it'd be you.

Literal LOL at TDWP…watching it once was more than enough *

Posted by PapaDels <iframe src='https://mb.boardhost.com/TheDeuce/info/user=PapaDels' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 21:21:50, in reply to "the list..."

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I have schweppervessence and wessonality.
Too sweet to be sour, too nice to be mean.

Definitely not a sci-fi fan*

Posted by CoronaTheirAss <iframe src='https://mb.boardhost.com/TheDeuce/info/user=CoronaTheirAss' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 19:21:53, in reply to "the list..."

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This video showed up on my YouTube feed and the title of the video…

Posted by OB25 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=OB25' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 19:01:15, in reply to "the list..."

made me think that there are few things I’d want to watch less than this.

And seeing the list validates that opinion.

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When something is happening, young people like to say it’s “lit.”

Sideways was a terrible movie. Utterly lacking any interest, humor, or entertainment value.

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:45:34, in reply to "the list..."

And my recollection of Garden Stste was a fairly dull, mopey sort of thing that I can’t imagine rewatching.

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Also kind of shocked that 2 Fast/Furious movies made the list and no Mission Impossibles

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:59:44, in reply to "Sideways was a terrible movie. Utterly lacking any interest, humor, or entertainment value."

MI: 4 would probably top my list. And speaking of Tom Cruise, Edge of Tomorrow would also definitely be near the top as well.

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And my recollection of Garden Stste was a fairly dull, mopey sort of thing that I can’t imagine rewatching.

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found the merlot drinker!*

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:46:16, in reply to "Sideways was a terrible movie. Utterly lacking any interest, humor, or entertainment value."

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And my recollection of Garden Stste was a fairly dull, mopey sort of thing that I can’t imagine rewatching.

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I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

Merlot sucks, but not as much as that movie.*

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:50:51, in reply to "found the merlot drinker!*"

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And my recollection of Garden Stste was a fairly dull, mopey sort of thing that I can’t imagine rewatching.

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This is just a list of movies I enjoy watching while flipping around on my phone.*

Posted by Warrin'_Illini $<iframe src='https://mb.boardhost.com/TheDeuce/info/user=Warrin\'_Illini' width='330' height='300' border=0 style='border:none;'>$ on December 31, 2025, 13:40:04, in reply to "the list..."

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You cannot lose games in the NFL and still win.

on first glance, very little (if any) from post-2015

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:36:12, in reply to "the list..."

I know that says something about the state of modern cinema, especially in regards to the type of movie that tends to be on these lists. However, I think it says a lot more about this nearly-elderly man and his refusal to let go of his salad days.

I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

If you watch the podcast, which is entertaining

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:54:01, in reply to "on first glance, very little (if any) from post-2015"

He kind of says that he's biased towards older films because the others haven't been around as long for him to actual rewatch them.

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I've seen one of those!*

Posted by Stu <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Stu' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:34:05, in reply to "the list..."

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Who the fuck is rewatching The Social Network and Spotlight?*

Posted by biclops <iframe src='https://mb.boardhost.com/TheDeuce/info/user=biclops' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:31:07, in reply to "the list..."

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The way you are, it's not your fault, you knew that
The way we were, so young and caught up in it

This guy --->*

Posted by UofIL6 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=UofIL6' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:37:44, in reply to "Who the fuck is rewatching The Social Network and Spotlight?*"

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I’ve rewatched them both multiple times, but mostly on planes. *

Posted by VIV <iframe src='https://mb.boardhost.com/TheDeuce/info/user=VIV' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:34:25, in reply to "Who the fuck is rewatching The Social Network and Spotlight?*"

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"the sum value of my outfit will always be higher than yours."

I would absolutely rewatch The Social Network

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:32:44, in reply to "Who the fuck is rewatching The Social Network and Spotlight?*"

He said that Spotlight, while a tough watch, he likes the story of how a news organization pieces together a story.

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Both are such excellently made movies. *

Posted by VIV <iframe src='https://mb.boardhost.com/TheDeuce/info/user=VIV' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:34:52, in reply to "I would absolutely rewatch The Social Network"

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He said that Spotlight, while a tough watch, he likes the story of how a news organization pieces together a story.

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"the sum value of my outfit will always be higher than yours."

Agreed*

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:35:19, in reply to "Both are such excellently made movies. *"

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He said that Spotlight, while a tough watch, he likes the story of how a news organization pieces together a story.

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This appears to be a link to a podcast, not a list. *

Posted by assassin <iframe src='https://mb.boardhost.com/TheDeuce/info/user=assassin' width='330' height='300' border=0 style='border:none;'> on December 31, 2025, 13:22:51, in reply to "Bill Simmons Top 50 Most Rewatchable movies of the 21st Century"

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Brandon Schrock of Laredo, Texas, told the federal government that his employer was “poop,” and his occupation was “pooper.”

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