The List

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.

The Top 10

  1. 1. The Devil Wears Prada2006

  2. 2. The Social Network2010

  3. 3. Anchorman: The Legend of Ron Burgundy2004

  4. 4. The Town2010

  5. 5. The Departed2006

  6. 6. Miami Vice2006

  7. 7. The Hangover2009

  8. 8. Superbad2007

  9. 9. Taken2008

  10. 10. Step Brothers2008

11–50

  1. 11. Fast Five2011

  2. 12. Old School2003

  3. 13. Before Sunset2004

  4. 14. Spotlight2015

  5. 15. Sideways2004

  6. 16. Limitless2011

  7. 17. This Is the End2013

  8. 18. Bridesmaids2011

  9. 19. No Country for Old Men2007

  10. 20. Den of Thieves2018

  11. 21. Forgetting Sarah Marshall2008

  12. 22. Gone Girl2014

  13. 23. John Wick: Chapter 22017

  14. 24. Furious 72015

  15. 25. Creed2015

  16. 26. Ocean's Eleven2001

  17. 27. The Dark Knight2008

  18. 28. Moneyball2011

  19. 29. Hardball2001

  20. 30. Get Out2017

  21. 31. Funny People2009

  22. 32. A Star Is Born2018

  23. 33. Proof of Life2000

  24. 34. Blackhat2015

  25. 35. Garden State2004

  26. 36. Lost in Translation2003

  27. 37. Top Gun: Maverick2022

  28. 38. Man on Fire2004

  29. 39. Mean Girls2004

  30. 40. Collateral2004

  31. 41. Sicario2015

  32. 42. The Wolf of Wall Street2013

  33. 43. Wedding Crashers2005

  34. 44. Borat2006

  35. 45. Miracle2004

  36. 46. The Equalizer2014

  37. 47. Flight2012

  38. 48. Knocked Up2007

  39. 49. A Lot Like Love2005

  40. 50. Just Go with It2011