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THE REWATCHABLES · December 29, 2025

Bill’s 50 Most Rewatchable Movies of the 21st Century

A movie directed by N/A, covered in the complete Rewatchables archive.

Directed by N/A
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Movie year—Release year unavailable
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FROM THE CONVERSATION

What they said about the movie

Bill unveils and explains his personal top 50 most rewatchable movies of the 21st century, with Sean and Chris reacting, debating placements, and comparing the list to their own rewatch habits. The conversation mixes affection, playful disagreement, and a lot of genre-specific enthusiasm, especially for action movies, comedies, and comfort-watch favorites.
Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections

WHY IT WORKS

What made it rewatchable

  1. 01Movies can be dropped into at almost any point and still work as a viewing experience. About 24 min
  2. 02Comfort-watch movies tied to family viewing and repeat household play patterns matter more than formal metrics. Opening minutes
  3. 03Action movies with memorable set pieces and strong endings are especially rewatchable. About 40 min
  4. 04Comedies with endlessly repeatable jokes and ensemble chemistry dominate the list. About 1:04
  5. 05Movies that double as family or shared-viewing comfort watches reappear often. About 1:28

WHAT DID NOT WORK

Their main criticisms

  1. moderateKnocked Up loses momentum in its last half hour. About 16 min
  2. moderateWedding Crashers is strong early but sags after the first hour. About 16 min
  3. minorLimitless is surprising to place above some prestige favorites, even to the other hosts. About 1:04
  4. minorFast & Furious sequels after the early entries are hard for Chris and Sean to defend. About 48 min · medium confidence
  5. majorBill admits one major omission from the list: Zodiac. About 1:28

SCENES THEY KEPT COMING BACK TO

Standout moments

Favorite

Flight plane-crash / drunken takeoff sequence

Bill calls the crash montage and lead-in one of the most rewatchable stretches on YouTube.

About 24 min
Favorite

Top Gun Maverick final dogfight and runway sequence

Bill says the 10-minute stretch from Jon Hamm sending Maverick through the climax is perfect.

About 40 min
Favorite

The Hangover baby-dealing scene

Bill says the line about not being at the table is one of the funniest in any movie.

About 1:20
Favorite

Taken interrogation and gun violence sequence

Bill highlights the arm-shooting and interrogation as part of the movie’s tight action design.

About 1:12
Favorite

No Country for Old Men hotel confrontation

Bill points to the tracker-in-the-suitcase sequence as a standout rewatchable stretch.

About 56 min
Favorite

Spotlight newsroom investigation process

Bill values the procedural puzzle-solving and the strong ensemble scenes.

About 1:20
Favorite

The Devil Wears Prada Paris/costume and office scenes

Bill says the movie is easy to put on at any time because every part works.

About 1:28

WHERE THEY DISAGREED

The biggest debates

They partly agreed Opening minutes

How much newer movies can compete with older rewatchables

Bill Simmons

He thinks newer films, especially from the last decade, have had less time to prove themselves.

Sean Fennessey

He agrees the list skews older and suggests time is part of rewatchability.

They partly agreed About 40 min

Whether horror movies belong in a rewatchables canon

Bill Simmons

He says he does not rewatch horror the same way, though he likes some titles.

Chris Ryan

He suggests family viewing habits and mood affect how often horror gets revisited.

They left it as a friendly argument About 1:20

The value of The Hangover versus Superbad

Bill Simmons

He puts The Hangover slightly ahead because of certain jokes and the ending.

Chris Ryan

He does not fully fight the ranking but shares the affection for both.

They agreed About 40 min

Top Gun Maverick as a cultural event versus a rewatchable favorite

Bill Simmons

He sees it as both a major moviegoing event and a repeatable scene machine.

Sean Fennessey

He emphasizes its broad cultural impact and technical excellence.

No final agreement About 1:20

Miami Vice’s quality

Bill Simmons

He ranks it very high and treats the admiration as legitimate.

Chris Ryan

He says the movie’s celebration is a delusion among middle-aged men and rejects it.

10 People discussedActors, directors, writers, and producers
12 Conversation takesSpeakers shown only where the transcript identifies them
Bill SimmonsLoved it

Just Go With It

He says it is a Simmons family classic and a major COVID-era comfort watch.

About 8 min
Bill SimmonsLoved it

A Lot Like Love

He defends it as a highly rewatchable rom-com with aging characters and a strong Kutcher performance.

About 8 min
Bill SimmonsLiked it

Knocked Up

He likes the first hour and many supporting bits but thinks the final act drags.

About 16 min
Bill SimmonsLoved it

The Equalizer

He calls it a textbook rewatchable and wishes more action movies like it existed.

About 16 min
Bill SimmonsLoved it

Man on Fire

He calls it a favorite Denzel performance and says it can be watched from any point.

About 16 min
Bill SimmonsLoved it

Top Gun Maverick

He regards it as a defining theatrical experience of the decade and a perfect stretch of movie-star filmmaking.

About 32 min
Bill SimmonsLiked it

Garden State

He finds it a fun hang and thinks it has been unfairly dismissed over time.

About 32 min
Bill SimmonsLoved it

Black Hat

He refuses to apologize for its place on the list and argues it rewards repeated viewing.

About 32 min
Bill SimmonsLiked it

Funny People

He says it is one of Sandler’s best acting performances, even if the ending is strange.

About 40 min
Bill SimmonsLoved it

Get Out

He calls it a great hang and an incredibly well-made film.

About 40 min
Bill SimmonsLoved it

Moneyball

He says it has a huge cultural footprint and Brad Pitt is the key reason it replays so well.

About 1:12
Bill SimmonsLoved it

The Devil Wears Prada

He says it is probably the movie he has watched the most and that it works for the whole family.

About 1:28
5 ThemesThe larger ideas in the discussion

Personal canon over objective ranking

Bill emphasizes the list is purely his own and based on his actual rewatch behavior rather than consensus quality.

Opening minutes

Family and household viewing habits

The ranking is shaped by what he, his wife, and his kids repeatedly watch together or around each other.

Opening minutes

Action-movie craft and scene memory

The hosts focus on signature scenes, endings, and set pieces as the clearest rewatchability markers.

About 40 min

Comedy as repeatable comfort

The show argues that comedies from the 2000s remain a core part of repeat viewing culture.

About 1:04

TV-era and streaming-era viewing changes

Bill and Sean discuss how modern viewing patterns, cable, streaming, and family preferences shape what gets rewatched.

About 56 min · medium confidence
21 Facts and referencesProduction notes and other movies mentioned

Production note

Bill excluded 2000 releases from the 21st-century list.

Opening minutes

Production note

Bill excluded documentaries from consideration.

Opening minutes

Production note

Bill excluded movies mainly watched because of his wife or kids unless they were also his own choices.

Opening minutes

Production note

Bill says his list was made without notes or computers during the conversation.

Opening minutes

Disputed in the episode

Bill admits Zodiac was supposed to be on the list but got cut by mistake.

About 1:28

Production note

Bill says the number-one and number-two movies on his list are both getting sequels in 2026.

About 1:28

Heat

Bill recalls doing Heat early in the show’s history and uses it as a marker for the pod’s longevity.

Opening minutes

The Holiday

Bill excludes it because it was mostly his wife’s choice, despite frequent household play.

Opening minutes

Love Actually

Another wife-driven household repeat that Bill excludes from his own canon.

Opening minutes

Grey’s Anatomy

Used to describe his wife’s TV-heavy viewing habits and contrast with movie habits.

About 8 min · medium confidence

Regretting You

Bill and Sean discuss it as a ridiculous, unintentionally funny melodrama they watched recently.

About 8 min · medium confidence

The Watch

Chris is introduced as being seen on The Watch.

Opening minutes · low confidence

25th Hour

Bill references it as a previously controversial high placement on another list.

Opening minutes

Crohn’s / ulcerative colitis ad copy

The episode opens with unrelated ad reads before the conversation begins.

Opening minutes · low confidence

State Farm

Sponsor read used to transition into the episode.

Opening minutes · low confidence

Timothée Chalamet

Sean jokes about a surprise guest possibility and Bill says he might keep him to himself.

Opening minutes · medium confidence

Amanda

Bill refers to Amanda as his list-making partner for some prior rankings.

About 1:28 · medium confidence

Zoe

Bill discusses her TV-heavy taste and some teen romances she likes.

About 8 min · medium confidence

John Candy

Sean and Bill briefly discuss a documentary and Bill’s rating of Bill Murray.

About 48 min · medium confidence

All the President’s Men

Bill uses it as a comparison for Spotlight’s investigative appeal.

About 1:20

The Nice Guys

Bill and Sean discuss it as a future rewatchable contender and possible sequel title joke.

About 1:28 · medium confidence
10 Running jokes and short linesRecurring bits captured from the conversation

No-notes list reveal

Bill repeatedly reminds Sean he brought no notes and is revealing the list live from memory.

Opening minutes

CR’s restaurant-repeat habit

Sean’s tendency to return quickly to a favorite restaurant and order the same thing is used as a rewatchability analogy.

About 8 min

What’s the movie? / premise improv

Bill and Sean riff on plotting and inventing or misremembering movie premises, especially around melodramas and thrillers.

About 8 min

Movie-star appreciation lists

Bill and Sean repeatedly spin off side rankings, like Kutcher’s best performances or Denzel’s best work.

About 8 min

Franchise comparisons

The hosts compare franchises such as Taken, Equalizer, John Wick, and Fast & Furious to define what kind of action movie is most rewatchable.

About 24 min

Bill Simmons

“time is luck”
Opening minutes

Bill Simmons

“not at the table, Carlos”
About 1:20

Bill Simmons

“stuff of legends”
About 32 min

Bill Simmons

“The heart wants what the heart wants”
About 8 min

Bill Simmons

“I didn't say the list made sense”
About 1:04

ON THE MIC

3 voices on this episode

Bill Simmons headshotBill SimmonsThe Rewatchables
Chris Ryan headshotChris RyanThe Rewatchables
Sean Fennessey headshotSean FennesseyThe Rewatchables

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