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

Podcast: The Rewatchables

Published: 2025-12-30

Duration: 1 hr 37 min

Guests: Sean Fennessey, Chris Ryan

Summary

Bill Simmons counts down his top 50 most rewatchable films of the 21st century, excluding films from 2000, documentaries, and some personal favorites, with Sean Fennessey and Chris Ryan offering their insights.

What Happened

Bill Simmons presents his list of the 50 most rewatchable movies from 2001 onwards, with Sean Fennessey and Chris Ryan joining in to discuss their own favorites and insights. The list begins with 'Just Go With It' at number 50, a film that became a family favorite during COVID, and includes other films like 'A Lot Like Love' and 'Knocked Up' for their personal appeal and comedic elements. The hosts also discuss the cultural impact and rewatchability of films such as 'The Wolf of Wall Street' and 'The Dark Knight', which are praised for their pace and iconic scenes. Bill's list features a mix of genres, from action-packed films like 'John Wick 2' to comedies like 'Anchorman', reflecting a broad range of tastes and preferences.

The list highlights films that are not only personally significant to Bill, but also have a wider cultural resonance, such as 'Top Gun: Maverick' and 'Bridesmaids'. Sean Fennessey and Chris Ryan contribute their own frequently rewatched films, with Chris mentioning 'Sicario' and 'Miami Vice' as his go-to movies for rewatchability. The discussion touches on films that have aged well over time, such as 'Miami Vice' and 'No Country for Old Men', with the latter being appreciated more for its ending as the hosts have aged.

Bill Simmons notes the importance of strong performances and memorable scenes, citing films like 'The Departed' and 'Gone Girl' for their standout acting by Leonardo DiCaprio, Matt Damon, and Ben Affleck. The episode also explores the idea of films gaining relevance over time, with 'The Social Network' being a prime example of a movie that has become increasingly significant as the world of social media evolves.

The hosts discuss how personal and family preferences influence Bill's list, as seen with 'Mean Girls', a film appreciated by his whole family, and 'Bridesmaids', a favorite of his wife's. The episode also includes discussions about films that didn't make the cut, such as 'Zodiac', which Bill regrets omitting, and 'Almost Famous', which was excluded due to its release year.

Overall, the episode provides a comprehensive look at the elements that make a movie rewatchable, from strong narratives and performances to cultural impact and personal connections. Bill Simmons' list serves as a reflection of both his personal tastes and the broader trends in cinema over the past two decades. Sean and Chris add depth to the conversation by offering their own perspectives and frequently rewatched films, making for a rich discussion on the topic of rewatchability.

The episode is sponsored by several companies, including United Airlines, which promotes their app with personalized airport maps and real-time flight updates, and State Farm, which emphasizes the importance of choices in insurance coverage.

Key Insights