December 30, 2025
Bill's 50 Most Rewatchable Movies of the 21st Century
In a special edition of The Rewatchables, Bill Simmons is joined by Sean Fennessey and Chris Ryan to reveal his 50 most rewatchable movies of the 21st century.
Notes
- Special list episode – Bill's personal 50 most rewatchable movies of the 21st century.
- Rules: no 2000 movies (belong to last century), no documentaries, no movies his wife watches that he just jumps in and out of ('The Holiday', Love Actually, Nancy Meyers movies), no movies his son picked that he watched along with (Mid 90s, Big Time Adolescence).
- The list favors 2001-2010 movies; newer movies haven't had enough time yet.
- The list:
- 'Just Go with It'
- 'A Lot Like Love'
- 'Knocked Up'
- 'Flight'
- 'The Equalizer'
- 'Miracle'
- 'Borat'
- 'Wedding Crashers'
- 'The Wolf of Wall Street'
- 'Sicario'
- 'Collateral'
- 'Mean Girls'
- 'Man on Fire'
- 'Top Gun: Maverick'
- 'Lost in Translation'
- 'Garden State'
- 'Blackhat'
- 'Proof of Life' 'Zodiac'
- 'A Star Is Born'
- 'Funny People'
- 'Get Out'
- 'Hardball'
- 'Moneyball'
- 'The Dark Knight'
- 'Ocean's Eleven'
- 'Creed'
- 'Furious 7'
- 'John Wick: Chapter 2'
- 'Gone Girl'
- 'Forgetting Sarah Marshall'
- 'Den of Thieves'
- 'No Country for Old Men'
- 'Bridesmaids'
- 'This Is the End'
- 'Limitless'
- 'Sideways'
- 'Spotlight'
- 'Before Sunset'
- 'Old School'
- 'Fast Five'
- 'Step Brothers'
- 'Taken'
- 'Superbad'
- 'The Hangover'
- 'Miami Vice'
- 'The Departed'
- 'The Town'
- 'Anchorman'
- 'The Social Network'
- 'The Devil Wears Prada'
- Sean was surprised by Devil Wears Prada at #1. Bill explains: his wife and daughter's favorite movie, he always gets sucked in when it's on, he's seen it the most times, and it achieves 'Rewatchables perfection.'
- Both Social Network (#2) and Devil Wears Prada (#1) were getting sequels in 2026.
- Controversial picks included: 'Blackhat' at 34, 'Proof of Life' at 33, 'Limitless' at 16 (over Dark Knight and No Country), and two Fast & Furious movies in the top 25.
- Sean called 'Miami Vice' (#6) 'a mass delusion among middle-aged men' – he saw it once in theaters and never went back.