Bill's 50
On the December 29, 2025 episode, Bill Simmons counted down his 50 Most Rewatchable Movies of the 21st Century — his list, his order, revealed from 50 to 1 while Chris Ryan and Sean Fennessey objected. 45 of the 50 have their own Rewatchables episode.
1. The Devil Wears Prada, score 7.42
2006
2. The Social Network, score 9.29
2010
3. Anchorman: The Legend of Ron Burgundy
2004
4. The Town, score 8.63
2010
5. The Departed 2006, score 9.68
6. Miami Vice 2006, score 6.91
7. The Hangover 2009, score 8.52
8. Superbad 2007, score 9.06
9. Taken 2008, score 7.99
10. Step Brothers 2008, score 7.03
11. Fast Five 2011, score 7.95
12. Old School 2003, score 6.96
13. Before Sunset 2004, score 8.90
14. Spotlight 2015, score 8.69
15. Sideways 2004, score 8.88
16. Limitless 2011, score 7.77
17. This Is the End 2013, score 7.84
18. Bridesmaids 2011, score 8.03
19. No Country for Old Men 2007, score 8.92
20. Den of Thieves 2018, score 7.98
21. Forgetting Sarah Marshall 2008, score 8.64
22. Gone Girl 2014, score 8.39
23. John Wick: Chapter 2 2017, score 8.22
24. Furious 7 2015, score 7.98
25. Creed 2015, score 8.64
26. Ocean's Eleven 2001, score 8.27
27. The Dark Knight 2008, score 9.19
28. Moneyball 2011, score 8.69
29. Hardball 2001, score 7.19
30. Get Out 2017, score 8.68
31. Funny People 2009
32. A Star Is Born 2018, score 8.28
33. Proof of Life 2000, score 6.80
34. Blackhat 2015, score 6.35
35. Garden State 2004
36. Lost in Translation 2003, score 9.38
37. Top Gun: Maverick 2022, score 8.78
38. Man on Fire 2004, score 7.51
39. Mean Girls 2004, score 8.53
40. Collateral 2004, score 8.49
41. Sicario 2015, score 8.88
42. The Wolf of Wall Street 2013, score 8.65
43. Wedding Crashers 2005, score 7.38
44. Borat 2006, score 8.46
45. Miracle 2004, score 7.59
46. The Equalizer 2014, score 7.88
47. Flight 2012, score 8.90
48. Knocked Up 2007, score 8.46
49. A Lot Like Love 2005
50. Just Go with It 2011