Bill Simmons' Most Rewatched Movies of the 21st Century List is Insane
The Ringer head gave movie fans something to debate over the weekend.

'The Devil Wears Prada'
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.
- The Devil Wears Prada
- The Social Network
- Anchorman
- The Town
- The Departed
- Miami Vice
- Hangover
- Superbad
- Taken
- Step Brothers
- Fast 5
- Old School
- Before Sunset
- Spotlight
- Sideways
- Limitless
- This Is The End
- Bridesmaids
- No Country For Old Men
- Den of Thieves
- Forgetting Sarah Marshall
- Gone Girl
- John Wick 2
- Fast 7
- Creed
- Oceans 11
- Dark Knight
- Moneyball
- Hard Ball
- Get Out
- Funny People
- A Star Is Born
- Proof of Life
- Black Hat
- Garden State
- Lost in Translation
- Top Gun Maverick
- Man On Fire
- Mean Girls
- Collateral
- Sicario
- The Wolf of Wall Street
- Wedding Crashers
- Borat
- Miracle
- The Equalizer
- Flight
- Knocked Up
- A Lot Like Love
- 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.










