The Rewatchables

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

December 30, 2025

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  • Bill Simmons compiled his personal list of the 50 most rewatchable movies of the 21st century (starting in 2001), applying specific caveats like excluding films from the year 2000 and movies primarily watched due to his wife's preference. 
  • The initial segment of the countdown reveals Bill's criteria for rewatchability often favor movies that are fun to jump into at any point, leading to a mix of comedies (like 'Just Go With It' at #50) and action/dramas ('Flight' at #47, 'The Equalizer' at #46). 
  • The early rankings show a strong presence of Denzel Washington films ('Flight,' 'The Equalizer,' 'Man on Fire') and a surprising inclusion of 'Black Hat' at #34, which Chris Ryan apparently did not watch properly. 
  • Bill Simmons' final ranking for his 50 most rewatchable movies of the 21st Century places *The Devil Wears Prada* at number one, followed by *The Social Network* at number two, and *Anchorman* at number three. 
  • The discussion highlights a strong presence of comedies in the top 25, with *Step Brothers* ranking 10th and *The Hangover* ranking 7th, suggesting a personal bias toward rewatchable humor. 
  • The hosts acknowledge that *Zodiac* was accidentally omitted from the final list despite being a highly rewatched film for Bill Simmons, indicating the difficulty of finalizing such a comprehensive ranking. 

Segments

Podcast Introduction and Guests
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(00:01:13)
  • Key Takeaway: The episode features Bill, Chris Ryan, and Sean Fennessey, with Bill surprising them by not revealing the topic beforehand.
  • Summary: Bill introduces Chris Ryan and Sean Fennessey. He mentions that he didn’t tell them the topic, leading to speculation about surprise guests (like Timothée Chalamet) or format changes (like a blind Rewatchables or mailbag).
Guessing the Episode Topic
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(00:01:55)
  • Key Takeaway: The hosts guessed several potential formats, including a blind Rewatchables, a mailbag, or a segment related to Cameron Crowe.
  • Summary: Sean guessed a porn set visit, Chris guessed a mailbag or a segment related to a previous conversation with Cameron Crowe, and another guess was a ‘merch haul’ or ‘five-year Oscars’ review. Bill reveals the topic is his personal list.
Revealing the List Topic
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(00:02:55)
  • Key Takeaway: Bill is presenting his personal list of the ‘50 most rewatchable movies of the 21st century,’ counting down from 50 to 1.
  • Summary: Bill confirms he is revealing his list of ‘50 most rewatchable movies of the 21st century,’ starting with number 50. He mentions that Sean previously did a ‘25 for 25’ list.
List Caveats and Exclusions
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(00:03:51)
  • Key Takeaway: Bill established several rules for his list, excluding movies from 2000, documentaries, and movies primarily watched due to his wife’s preference (like Nancy Meyers films).
  • Summary: Bill explains his caveats: no movies from the year 2000 (as the 21st century starts in 2001), no documentaries, and excluding movies like ‘The Holiday’ and ‘Love Actually’ which his wife watches frequently but aren’t his primary rewatch choices. He also excludes movies his son loves, like ‘Mid90s’.
Number 50: Just Go With It
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(00:10:27)
  • Key Takeaway: The first movie on the list, number 50, is the Adam Sandler/Jennifer Aniston comedy ‘Just Go With It,’ noted as a Simmons family classic.
  • Summary: Number 50 is ‘Just Go With It’ (2011). Bill notes it’s a family classic, especially during COVID, and mentions memorable scenes involving Brooklyn Decker.
Number 49: A Lot Like Love
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(00:11:50)
  • Key Takeaway: Number 49 is ‘A Lot Like Love’ (2004), praised for its structure spanning years and Ashton Kutcher’s performance.
  • Summary: Number 49 is ‘A Lot Like Love’ (2004), starring Amanda Peet and Ashton Kutcher. Bill defends Kutcher’s performance, and they discuss the structural element of characters aging across the film.
Number 48: Knocked Up
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(00:14:35)
  • Key Takeaway: ‘Knocked Up’ (2007) ranks at 48, with Bill liking the first hour but finding the last half hour weak.
  • Summary: Number 48 is ‘Knocked Up’ (2007). Bill praises the early scenes with Seth Rogen’s friends and Catherine Heigl’s work, but feels the movie falls apart later on.
Number 47: Flight
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(00:15:37)
  • Key Takeaway: ‘Flight’ (2012) is highly rewatchable due to its signature, meme-worthy scenes, particularly Denzel Washington’s hearing.
  • Summary: Number 47 is ‘Flight’ (2012). They discuss how the movie is hilarious to jump into, citing Denzel Washington’s NTSB hearing and the iconic crash scene set to ‘Feeling Alright.’
Number 46: The Equalizer
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(00:17:14)
  • Key Takeaway: Denzel Washington appears again at number 46 with ‘The Equalizer’ (2014), which Bill considers a ’textbook rewatchable.’
  • Summary: Number 46 is ‘The Equalizer’ (2014). They note this is the second Denzel film so far and discuss the franchise’s appeal, with Bill preferring the third installment.
Number 45: Miracle
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(00:18:35)
  • Key Takeaway: The first sports movie on the list is ‘Miracle’ (2004), which holds up well for rewatching the underdog victory.
  • Summary: Number 45 is ‘Miracle’ (2004). They acknowledge it has been on the show before and is a good rewatch for its speeches and the victory over the Russians.
Number 44: Unnamed Comedy
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(00:18:57)
  • Key Takeaway: Number 44 is an unnamed comedy that holds up well and provided some of the hardest laughs for Bill during COVID rewatches.
  • Summary: Number 44 is an unstated comedy that Bill rewatched during COVID. They discuss funny scenes involving Pamela Anderson and a wrestling scene in a hotel room.
Number 43: Wedding Crashers
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(00:19:34)
  • Key Takeaway: ‘Wedding Crashers’ (2005) ranks 43, praised for its ecstatic opening but criticized for losing steam in the second half.
  • Summary: Number 43 is ‘Wedding Crashers’ (2005). They praise the opening montage and the chemistry between Vince Vaughn and Owen Wilson, but note it suffers when the comedy gets sad.
Number 42: Wolf of Wall Street
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(00:21:20)
  • Key Takeaway: ‘The Wolf of Wall Street’ (2013) is highly rewatchable because no single scene feels too long, allowing viewers to jump in easily.
  • Summary: Number 42 is ‘The Wolf of Wall Street’ (2013). Bill notes that despite its length, hopping into sections works well because the pacing is so fast.
Number 41: Sicario
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(00:21:36)
  • Key Takeaway: ‘Sicario’ (2015) is placed at 41, with the hosts noting its strong performances and the memorable scene involving Jon Bernthal.
  • Summary: Number 41 is ‘Sicario’ (2015), directed by Denis Villeneuve. They briefly discuss the plot and praise the performances, particularly Jon Bernthal’s scene at Home Depot.
Break and Sponsor Reads
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(00:22:41)
  • Key Takeaway: The podcast takes a break, featuring ads for ‘Dead Man’s Wire’ and Nordstrom.
  • Summary: The hosts take a break. They discuss ‘Zodiac’ as an example of a thrilling true story movie before introducing the film ‘Dead Man’s Wire’ and an ad for Nordstrom holiday shopping.
Number 40: Collateral
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(00:24:02)
  • Key Takeaway: ‘Collateral’ (2004) is number 40, a Michael Mann film that has aged well and features great scenes like the jazz club sequence.
  • Summary: Number 40 is ‘Collateral’ (2004). Bill notes it’s a great Michael Mann film that has aged well, highlighting the jazz club scene and Mark Ruffalo’s role.
Number 39: Mean Girls
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(00:25:54)
  • Key Takeaway: ‘Mean Girls’ (2004) is number 39, considered an eternal comedy that appeals equally to Bill, his wife, and his daughter.
  • Summary: Number 39 is ‘Mean Girls’ (2004). They praise its smart writing, Tim Meadows’ performance, and its timeless quality regarding high school dynamics.
Number 38: Man on Fire
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(00:27:02)
  • Key Takeaway: ‘Man on Fire’ (2004) is number 38, a Tony Scott film Bill considers one of his favorite Denzel performances.
  • Summary: Number 38 is ‘Man on Fire’ (2004). Bill expresses strong affection for the film and Denzel Washington’s performance as John Creasy, noting Tony Scott’s stylish direction.
Number 37: Top Gun Maverick
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(00:28:15)
  • Key Takeaway: ‘Top Gun: Maverick’ (2022) is lower than expected at 37, but recognized as the best movie experience of the decade so far.
  • Summary: Number 37 is ‘Top Gun: Maverick’ (2022). Bill feels he hasn’t had enough time with it yet, but acknowledges its massive cultural impact and the fun of seeing it multiple times.
Number 36: Lost in Translation
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(00:30:19)
  • Key Takeaway: ‘Lost in Translation’ (2003) is number 36, praised for its music, pacing, and Bill Murray’s performance.
  • Summary: Number 36 is ‘Lost in Translation’ (2003). They discuss Bill Murray’s career trajectory and praise Scarlett Johansson’s performance and the film’s overall mood and ending.
Number 35: Garden State
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(00:32:06)
  • Key Takeaway: ‘Garden State’ (2004) ranks 35, which surprises Sean, as Bill finds it an enjoyable, sincere film that has become underrated over time.
  • Summary: Number 35 is ‘Garden State’ (2004). Bill defends the movie against potential eye-rolling, praising Zach Braff’s fit for the role and the sincerity of the story.
Number 34: Black Hat
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(00:33:42)
  • Key Takeaway: Number 34 is Michael Mann’s ‘Black Hat’ (2015), which Bill defends as an awesome movie despite its incoherence.
  • Summary: Number 34 is ‘Black Hat’ (2015). Bill unapologetically defends the film, noting it’s better on subsequent viewings once the plot is understood, while Chris expresses confusion.
Number 33: Proof of Life
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(00:34:43)
  • Key Takeaway: ‘Proof of Life’ (2000) is number 33, which Bill insists is much better than its reputation suggests, especially knowing the cut love scene.
  • Summary: Number 33 is ‘Proof of Life’ (2000), starring Russell Crowe and Meg Ryan. Bill champions the film, noting that knowing about the cut love scene between Crowe and Ryan improves the narrative coherence.
Number 32: A Star Is Born
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(00:38:00)
  • Key Takeaway: ‘A Star Is Born’ (2018) is number 32, enjoyed by the family except for Bill’s son, with the first hour being particularly strong.
  • Summary: Number 32 is ‘A Star Is Born’ (2018). They praise Lady Gaga’s performance and the early bar scene, noting that Bradley Cooper’s later public humiliation makes the sad ending funnier in retrospect.
Number 31: Funny People
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(00:39:26)
  • Key Takeaway: ‘Funny People’ (2009) is number 31, with Bill highlighting Adam Sandler’s best acting and the hilarious party scene celebrating his non-cancer diagnosis.
  • Summary: Number 31 is ‘Funny People’ (2009). Bill praises Sandler’s performance and the first 70 minutes, particularly the scene where he celebrates not having cancer.
Number 30: Get Out
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(00:42:40)
  • Key Takeaway: ‘Get Out’ (2017) is number 30, a solid film, though Bill finds Jordan Peele’s later films (‘Nope,’ ‘Us’) more rewarding for rewatching.
  • Summary: Number 30 is ‘Get Out’ (2017). Bill discusses his general reluctance to rewatch horror but praises this film’s initial thrill and Allison Williams’ performance.
Number 29: Hardball
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(00:44:12)
  • Key Takeaway: ‘Hardball’ (2001) is number 29, a Keanu Reeves sports movie that Bill considers a seminal event due to G-Baby’s death.
  • Summary: Number 29 is ‘Hardball’ (2001). Bill defends Keanu as an underrated sports movie actor and notes the emotional impact of the child character G-Baby dying.
Number 28: Moneyball
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(00:46:01)
  • Key Takeaway: ‘Moneyball’ (2011) is number 28, a universally liked film with a massive cultural footprint, featuring Brad Pitt’s best performance.
  • Summary: Number 28 is ‘Moneyball’ (2011). They recall a live screening where the audience erupted upon hearing the music, confirming its broad appeal.
Number 27: The Dark Knight
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(00:47:19)
  • Key Takeaway: ‘The Dark Knight’ (2008) is number 27, and Bill expresses a strong desire to discuss it one-on-one with Sean, favoring Bane over the Joker.
  • Summary: Number 27 is ‘The Dark Knight’ (2008). They discuss the film’s visual quality on 4K and debate whether Bane or the Joker is the superior villain.
Movie Transfer Talk
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(00:48:01)
  • Key Takeaway: A brief, unclear discussion about video feed transitions and 4K transfers.
  • Summary: The hosts briefly discuss what ’the kids call it’ when transitioning a video feed, settling on ’the transfer’ or ’the 4K transfer'.
Dark Knight Rises Fandom
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(00:48:15)
  • Key Takeaway: One host was deeply moved by a specific truck flip scene in The Dark Knight Rises.
  • Summary: A host describes crying during the truck flip scene near the end of The Dark Knight Rises, expressing it was the feeling they want from a movie. They then discuss a preference for Bane over the Joker.
Bane vs. Joker Election Hypothetical
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(00:48:47)
  • Key Takeaway: A humorous debate about whether Bane or Joker would win a hypothetical election.
  • Summary: The conversation shifts to a hypothetical election between Bane and Joker, with one host arguing Bane has greater ‘mind share’ and could win an election, leading to a tangent about political matchups.
Ocean’s 11 Discussion
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(00:49:36)
  • Key Takeaway: Ocean’s 11 is considered a wonderful hang featuring peak movie stars, but was surprisingly omitted from the final list.
  • Summary: Number 26 is revealed as Ocean’s 11. The hosts praise it as a ‘wonderful hang’ and a great movie featuring movie stars at their peak, acknowledging they overlooked it for the list.
Break and Ad Read
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(00:50:13)
  • Key Takeaway: The hosts announce a break before revealing the top 25, followed by advertisements.
  • Summary: Bill announces one more break before the top 25 countdown, followed by ads for EA Sports FC 26 and Apple Card.
Creed Ranking and List Flow
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(00:51:18)
  • Key Takeaway: Creed is a modern sports classic, and the list became easier to finalize after reaching number 24.
  • Summary: Number 25 is Creed, called a ’total modern classic’ sports movie. They discuss how the list composition felt easier once they hit number 24.
Fast & Furious 7 Tribute
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(00:52:34)
  • Key Takeaway: The ending of Fast & Furious 7, honoring Paul Walker, is considered one of the greatest movie endings of the 21st century.
  • Summary: Number 24 is Fast & Furious 7, the film where Paul Walker died. The hosts praise the execution of the ending tribute to Walker as ’the greatest ending of any movie in the 21st century'.
Fast Franchise Rewatchability
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(00:53:44)
  • Key Takeaway: The hosts have covered several Fast movies, but some hosts struggle to connect with Vin Diesel’s later performances.
  • Summary: They discuss which Fast movies they have covered on the podcast (The Fast and the Furious, Fast & Furious, Fast Five, Fast 7). One host admits finding it hard to watch Vin Diesel in the later films.
John Wick 2 Placement
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(00:55:21)
  • Key Takeaway: John Wick 2 is highly rewatchable, but John Wick 1 did not make the list.
  • Summary: Number 23 is John Wick 2, which one host was stunned didn’t crack the top 20. They praise Wick 2 as a home run for rewatchability, noting John Wick 1 was excluded.
Gone Girl’s Enduring Appeal
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(00:56:21)
  • Key Takeaway: Gone Girl remains highly rewatchable, especially due to Ben Affleck’s performance fitting his public persona.
  • Summary: Number 22 is Gone Girl. They discuss how it’s a movie you can jump into at any point and still be engaged, praising Affleck’s performance and the film’s structure.
Forgetting Sarah Marshall Appreciation
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(00:57:21)
  • Key Takeaway: Forgetting Sarah Marshall has aged wonderfully, featuring great comedic performances and the genius inclusion of the Dracula musical subplot.
  • Summary: Number 21 is Forgetting Sarah Marshall. They praise its aging quality, the cast (especially Mila Kunis and Russell Brand), and the meta-comedy involving the Dracula musical concept.
Top 20 Begins: Den of Thieves
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(00:59:40)
  • Key Takeaway: Den of Thieves is considered the best pure action movie rewatchable of the last decade by one host, narrowly beating John Wick 2.
  • Summary: The top 20 starts with number 20, Den of Thieves. They discuss its action credentials, noting Pablo Schreiber and 50 Cent’s roles, and how it narrowly edges out John Wick 2 for pure action rewatchability.
No Country for Old Men’s Classic Status
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(01:01:06)
  • Key Takeaway: No Country for Old Men is now considered a timeless American classic whose ending is profoundly appreciated.
  • Summary: Number 19 is No Country for Old Men. The host who initially disliked the ending now finds it profound, comparing the film’s timeless quality to classics like Casablanca.
Bridesmaids’ Loaded Cast
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(01:03:05)
  • Key Takeaway: Bridesmaids is a beloved, hard-R comedy that is tragic to see as an end of an era, featuring an incredibly loaded cast.
  • Summary: Number 18 is Bridesmaids. They lament the decline of big-budget R-rated comedies and praise the stacked cast, including Melissa McCarthy’s breakout role and Rose Byrne’s performance.
This Is The End as Time Capsule
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(01:04:12)
  • Key Takeaway: This Is The End serves as a perfect time capsule of Hollywood stars right before a major shift in the industry.
  • Summary: Number 17 is This Is The End. They note it’s a comedy that is hard to discuss without just laughing, and it captures a specific era of Hollywood talent.
Limitless’s High Rewatch Frequency
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(01:05:10)
  • Key Takeaway: Limitless is highly rewatched, especially by one host who wishes for the NZT drug during busy work days.
  • Summary: Number 16 is Limitless. They discuss how often it’s on TV and how relevant the concept of cognitive enhancement feels, noting Bradley Cooper’s breakout performance.
Sideways’ Quiet Charm
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(01:07:50)
  • Key Takeaway: Sideways is appreciated for its focus on character and the great performances by Thomas Haden Church and Virginia Madsen.
  • Summary: Number 15 is Sideways. They highlight the wine tasting setting, Thomas Haden Church’s character arc, and Virginia Madsen’s monologue.
Spotlight’s Difficult Rewatchability
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(01:08:37)
  • Key Takeaway: Spotlight is a controversial pick because it’s a tough rewatch, but its procedural excellence makes it endlessly rewatchable.
  • Summary: Number 14 is Spotlight. They acknowledge it’s a tough rewatch but compare its appeal to All the President’s Men—the satisfaction of watching a complex investigation come together.
Before Sunset’s Emotional Weight
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(01:10:03)
  • Key Takeaway: Before Sunset is a rough watch because it explores the difficult reality of marital honesty and the consequences of divorce.
  • Summary: Number 13 is Before Sunset. They discuss how the film explores the boundary of honesty in a long-term relationship and why it’s a ‘hard movie’ to revisit.
Old School’s Enduring Influence
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(01:11:10)
  • Key Takeaway: Old School is an influential 2000s comedy that remains highly rewatchable, featuring a crucial Luke Wilson performance.
  • Summary: Number 12 is Old School. They note its influence and how it favors the 2000s era of comedy. They also recall Cameron Crowe agreeing with the take that Luke Wilson could have been Harrison Ford.
Fast Five’s Peak Formula
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(01:12:13)
  • Key Takeaway: Fast Five is the peak of the Fast franchise, balancing unrealistic action with the introduction of The Rock.
  • Summary: Number 11 is Fast Five. They praise it as an unbelievable achievement, featuring great set pieces and one of the best action movie endings of the century, marking the peak before the series got too ambitious.
Step Brothers’ Comedy Staple
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(01:13:27)
  • Key Takeaway: Step Brothers is the highest-ranked comedy on the list and a staple for the Simmons family, known for its quotable absurdity.
  • Summary: Number 10 is Step Brothers. They call it immaculate and note it’s the comedy they’ve rewatched the most, highlighting Richard Jenkins’ dinosaur monologue.
Taken’s Perfect Tightness
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(01:14:24)
  • Key Takeaway: Taken is a perfect, tight 90-minute action film that serves as a great father-daughter watch.
  • Summary: Number 9 is Taken. They praise its 90-minute runtime as ‘perfect’ and ’tight,’ contrasting it with longer action films, and discuss the famous ‘flesh wound’ trope.
Superbad vs. The Hangover
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(01:17:02)
  • Key Takeaway: The Hangover narrowly edged out Superbad for the 7th spot due to specific, hilarious lines.
  • Summary: Number 8 is Superbad, followed by number 7, The Hangover. They discuss the close battle between the two Apatow-era comedies, with The Hangover winning due to lines like ‘Not at the table, Carlos.’
Miami Vice’s Aged Quality
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(01:18:35)
  • Key Takeaway: Miami Vice has aged incredibly well and is highly rewatchable, despite the lead actor having little memory of making it.
  • Summary: Number 6 is Miami Vice. They praise its look and rewatchability, noting that Colin Farrell seemed surprised by how much they liked it during a podcast interview.
The Departed’s Definition of Rewatchable
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(01:21:25)
  • Key Takeaway: The Departed is the definition of a rewatchable film, featuring peak Leo, Damon, and a deranged Nicholson.
  • Summary: Number 5 is The Departed. They call it the definition of rewatchable and note it might be Jack Nicholson’s last great performance.
The Town Over The Departed
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(01:22:10)
  • Key Takeaway: The Town ranks higher than The Departed based purely on the host’s personal rewatch frequency, tied to geographical familiarity.
  • Summary: Number 4 is The Town, ranked above The Departed based on rewatch count. The host cites his geographical ties to Boston and the North End as boosting its rewatch value.
Anchorman’s Comedy Peak
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(01:23:59)
  • Key Takeaway: Anchorman is the highest-ranked comedy, inducing near-hallucinatory laughter due to its perfectly delivered absurdity.
  • Summary: Number 3 is Anchorman. They praise its immaculate status and how rewatching it feels like memorizing a song. They note that Wake Up Ron Burgundy is also excellent.
Social Network’s Growing Relevance
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(01:25:23)
  • Key Takeaway: The Social Network has gained relevance as more is known about Mark Zuckerberg, making its Sorkin script even better.
  • Summary: Number 2 is The Social Network. They discuss how the film’s reputation has only grown and mention the upcoming sequel, which Sorkin is writing and directing.
Devil Wears Prada: Rewatch Perfection
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(01:27:05)
  • Key Takeaway: The Devil Wears Prada is Bill’s number one because it achieves ‘rewatchables perfection’—it’s ageless, universally appealing, and frequently watched by his family.
  • Summary: Number 1 is The Devil Wears Prada. Bill explains it’s the movie he and his family gravitate toward most often, praising Meryl Streep’s performance and its enduring fun.
Post-List Regrets and Zodiac Omission
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(01:34:21)
  • Key Takeaway: The biggest regret from the final list is the accidental omission of Zodiac from the top 50.
  • Summary: After revealing the list, Bill expresses regret over cutting Zodiac while shuffling positions, noting it would have been high on his personal rewatch list alongside There Will Be Blood and Inglourious Basterds.