When I am having a particularly hard day or am stuck in some part of a new screenplay, I turn to some of my comfort movies to inspire me and/or make me feel good.

And I know I'm not alone in that feeling. All over the globe, people find comfort in watches and go back to them again and again.

Recently, Bill Simmons, who is the head of The Ringer and one of the rotating guests on The Big Picture Podcast, sat down with hosts Sean Fennessey and Amanda Dobbins to talk about the 50 movies he has rewatched the most

The list was kind of bonkers and featured a ton of titles I could not have predicted at all.

Let's dive in.


Bill Simmons' Most Rewatched Movies of the 21st Century List

I love this podcast, and if you're a fan of movies, I think it's a must-listen. It's such a great hangout podcast, one where you feel like you're friends with the hosts, and you get to know them and their taste.

Bill is one of those guys who I have followed since Grantland days. I have no idea if I like him; he's got a ton of hot takes, but I think his websites have assembled the best people, and I can't deny that when he delivers lists like this one, they become viral sensations.

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

Unpacking the List 

If you watched the podcast, you know everyone sort of made fun of Bill's list, but I think it revealed a lot of deeply personal and fun things about him. There are a lot of movies on there that made me want to rewatch them.

There were also a ton that I had only ever watched once and had not ever considered going back to. And I feel like I somehow know more about who Bill is and what he loves in life as well.

Of course, there's a little too much Boston on here for me, a Philly fan, but I love when people unpack the movies that make them who they are.

Not only can you learn a lot about someone by walking a mile in their shoes, but seeing them over time and reaching out to them also reveals a lot, too.

This list inspired me to make one of my own, which I put on my Letterboxd and had fun assembling!

Let us know what you think your most rewatched movies are in the comments.