The Rewatchables Bill’s 50 Most Rewatchable Movies of the 21st Century | With Sean Fennessey and Chris Ryan
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Dec 30, 2025 
In this engaging discussion, film critic Sean Fennessey and writer Chris Ryan join Bill Simmons to break down the 50 most rewatchable movies of the 21st century. They dive into Bill's intriguing criteria for selection and highlight why certain films, like 'Knocked Up' and 'Get Out', beckon for repeat viewings. The trio humorously debates entries from rom-coms to action flicks, with the top three sparking lively conversation – particularly Bill’s surprising choice of 'Devil Wears Prada' as the ultimate rewatchable gem!
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How Bill Built His 50-Movie List
- Bill describes compiling a personal list of his 50 most-rewatchable 21st-century films and the rules he used to make it.
- He explains exclusions like 2000 films, documentaries, and movies his wife watches more than he does.
Recency Bias In Rewatchable Lists
- Bill notes list-making biases favor older movies because newer films haven't had time to accumulate rewatches.
- He admits newer releases (e.g., Once Upon a Time in Hollywood) felt premature to include despite liking them.
Household Viewing Shapes The List
- Bill explains he excluded many films his wife watches frequently (e.g., The Holiday, Love Actually, Nancy Meyers movies).
- He frames this as household viewing dynamics altering what counts as his personal rewatchable set.