Bill’s 50 Most Rewatchable Movies of the 21st Century | With Sean Fennessey and Chris Ryan

Bill is joined by Chris Ryan and Craig Horlbeck to read listener submissions for new categories as we gear up for 2026 on The Rewatchables. Producers: Craig Horlbeck, Chia Hao Tat, and Eduardo Ocampo Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Producers: Craig Horlbeck, Chia Hao Tat, Eduardo Ocampo, and Chris Wohlers Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Ringer’s Bill Simmons, Chris Ryan, and Van Lathan revisit one of the best movies of 2025,  Joseph Kosinski’s ‘F1,’ starring Brad Pitt, Kerry Condon, Damson Idris, and Javier Bardem. Producers: Craig Horlbeck, Chia Hao Tat, and Eduardo Ocampo A State Farm agent can help you choose the coverage you need. Like a good neighbor, State Farm is there.®Through the Subaru Share the Love® Event, Subaru and our retailers donate to charity for every new vehicle purchased or leased. Learn more about the charities Subaru and our retailers support at https://Subaru.com/share. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Bill and Chris honor Rob Reiner by revisiting one of their favorite ’80s movies, ‘The Sure Thing,’ starring John Cusack and Daphne Zuniga and directed by Rob Reiner. Producers: Craig Horlbeck, Chia Hao Tat, and Eduardo Ocampo A State Farm agent can help you choose the coverage you need. Like a good neighbor, State Farm is there.® Learn more about your ad choices. Visit podcastchoices.com/adchoices

What came first, the music or the misery? The Ringer’s Bill Simmons, Chris Ryan, Joanna Robinson, and Rob Mahoney pick up a shift at Championship Vinyl to revisit ‘High Fidelity,’ starring John Cusack, Jack Black, Lisa Bonet, Iben Hjejle, and Todd Louiso. Producers: Craig Horlbeck, Chia Hao Tat, Eduardo Ocampo, and Chris Thomas A State Farm agent can help you choose the coverage you need. Like a good neighbor, State Farm is there.® Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Ringer’s Bill Simmons and Sean Fennessey are joined by writer-director Cameron Crowe to discuss one of his favorite movies, ‘Shampoo,’ starring Warren Beatty, Julie Christie, Jack Warden, and Goldie Hawn. Producers: Craig Horlbeck, Chia Hao Tat, and Eduardo Ocampo A State Farm agent can help you choose the coverage you need. Like a good neighbor, State Farm is there.® Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Ringer’s Bill Simmons, Chris Ryan, and Van Lathan feel like a Kentucky Fried idiot after rewatching their 12th Sylvester Stallone movie on The Rewatchables, ‘Rocky II,’ also starring Carl Weathers and Talia Shire. Producers: Craig Horlbeck, Chia Hao Tat, and Eduardo Ocampo A State Farm agent can help you choose the coverage you need. Like a good neighbor, State Farm is there.® Learn more about your ad choices. Visit podcastchoices.com/adchoices

Uh-oh, The Ringer’s Bill Simmons, Chris Ryan, and Cousin Sal are gambling again! The guys fire up their favorite Monday night parlay after revisiting the 2005 sports thriller ‘Two for the Money,’ starring Matthew McConaughey, Al Pacino, and Rene Russo. Producers: Craig Horlbeck, Chia Hao Tat, and Eduardo Ocampo Through the Subaru Share the Love® Event, Subaru and our retailers donate to charity for every new vehicle purchased or leased. Learn more about the charities Subaru and our retailers support at https://Subaru.com/share. A State Farm agent can help you choose the coverage you need. Like a good neighbor, State Farm is there.® Learn more about your ad choices. Visit podcastchoices.com/adchoices

There's going to be sex, drugs, rock ’n’ roll, chips, dips, chains, whips … your basic Rewatchables episode. The Ringer’s Bill Simmons and Kyle Brandt revisit John Hughes’s 1985 hit ‘Weird Science,’ starring Anthony Michael Hall, Kelly LeBrock, and Ilan Mitchell-Smith. Producers: Craig Horlbeck, Chia Hao Tat, and Eduardo Ocampo Talk to a State Farm agent today to learn how you can choose to bundle and save with the Personal Price Plan®. Like a good neighbor, State Farm is there®. Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Ringer’s Bill Simmons, Sean Fennessey, and Van Lathan are the kings of the sewer after rewatching Brian De Palma’s ‘Snake Eyes,’ starring Nic Cage, Gary Sinise, and Carla Gugino. Producers: Craig Horlbeck, Chia Hao Tat, and Eduardo Ocampo This episode is brought to you by PayPal. Make the most of your money this holiday. Get 5% cash back when you Pay in 4 all holiday long, visit the PayPal app to save the offer. Expires 12/31. See paypal.com/promoterms. Subject to approval. Learn more at paypal.com/payin4. PayPal, Inc. NMLS #910457 Learn more about your ad choices. Visit podcastchoices.com/adchoices