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THE REWATCHABLES · February 6, 2020

Once Upon a Time…in Hollywood

A 2019 drama / comedy directed by Quentin Tarantino, covered in the complete Rewatchables archive.

DramaComedy2010sDirected by Quentin Tarantino
Overall episode#117Source sheet order
Movie year20192010s
Tomatometer86%Critics’ score
Metacritic84View score
Roger Ebert—No review recorded
DirectorQuentin TarantinoDrama / Comedy

FROM THE CONVERSATION

What they said about the movie

The hosts argue that the movie is likely to age as a major Tarantino statement about fame, career decline, memory, and Hollywood mythology, with especially strong praise for Brad Pitt and Leonardo DiCaprio. They treat it as unusually sentimental for Tarantino, visually immersive, and built around a series of highly rewatchable set pieces.
Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections

WHY IT WORKS

What made it rewatchable

  1. 01Brad Pitt’s trailer sequence is treated as a showcase of charisma and small details that make the scene endlessly replayable. About 24 min
  2. 02The Musso & Frank’s exchange and the drive afterward establish the film’s central career-crisis engine in a highly rewatchable run of scenes. About 16 min
  3. 03The Bruce Lee fight scene is admired as both funny and revealing, especially for Cliff’s false-memory quality. About 24 min
  4. 04Sharon Tate watching herself in the theater is seen as a pure, tender scene that encapsulates the film’s emotional project. About 24 min
  5. 05The Rick-at-home rehearsal and meltdown over his lines is singled out as one of the film’s funniest and most rewatchable stretches. About 32 min
  6. 06The Spahn Ranch sequence is praised for its tension, dogs, and dread, even if its impact softens after the first viewing. About 32 min

WHAT DID NOT WORK

Their main criticisms

  1. moderateThe Steve McQueen casting is viewed as one of the movie’s weakest elements and feels miscast. About 48 min
  2. minorThe Bruce Lee scene’s notoriety and backlash remain a possible sticking point, even though the hosts defend its purpose. About 24 min · medium confidence
  3. minorThe Spahn Ranch sequence loses some force on repeat viewings because the outcome is already known. About 40 min

SCENES THEY KEPT COMING BACK TO

Standout moments

Favorite

Musso & Frank’s career speech

Pacino tells Rick his career is over unless he reinvents himself, giving the movie its central career-spiral premise.

About 16 min
Favorite

Parking lot / car ride after Musso & Frank’s

Rick’s meltdown in the car crystallizes his panic about falling into Italian movies and declining status.

About 16 min
Favorite

Cliff in the trailer

Cliff alone with Brandy, TV Guide, and a shabby TV is praised as a tiny but captivating character scene.

About 24 min
mixed

Bruce Lee rooftop fight

A flashy, controversial memory scene that the hosts interpret as a false recollection revealing Cliff’s unreliability.

About 24 min
Favorite

Sharon Tate at the theater

Tate watches herself onscreen and buys her ticket; the hosts read this as a pure, tender expression of her career beginning.

About 24 min
Favorite

Rick practicing lines in the pool

Rick memorizes dialogue while floating in the pool and making whiskey sours, then spirals into frustration.

About 32 min
positive

Cliff picks up the hitchhiker

The ride to the ranch, with driving music and conversational tension, is treated as classic Tarantino cruising.

About 32 min
critical

Spahn Ranch arrival

The ranch sequence builds horror-movie dread through dogs, desolation, and Cliff’s unflappable presence.

About 32 min
Favorite

Final Manson home invasion

The acid-fueled attack turns into an action-comedy catharsis where Cliff does the work and Rick gets the glory.

About 40 min

WHERE THEY DISAGREED

The biggest debates

They left it as a friendly argument About 8 min

Whether the film is more Brad Pitt’s movie or Leonardo DiCaprio’s movie

Bill Simmons

Pitt wins the movie because the role restores and elevates him into an all-time star performance.

Chris Ryan

DiCaprio wins the movie because Rick Dalton is more complex, varied, and central to the film’s emotional structure.

Sean Fennessey

Pitt’s performance is the key revelation, but Leo’s work is also astonishing.

They agreed About 24 min

How to interpret the Bruce Lee scene

Bill Simmons

It is mainly a false-memory sequence showing Cliff’s delusion and unreliability.

Chris Ryan

It is a memory piece that should not be read as literal insult to Bruce Lee.

They agreed About 16 min

Whether the movie deserved more Sharon Tate scenes

Bill Simmons

No; the movie’s point is to contrast her career’s beginning with Rick’s decline.

Chris Ryan

Agrees that the film is doing a memory/history project and does not need more Tate exposition.

They partly agreed About 32 min

How effective the Spahn Ranch sequence is on repeat viewing

Bill Simmons

Still excellent, with dread and survival tension.

Chris Ryan

The first viewing is strongest because the ending surprise is gone later.

They agreed About 48 min

Who should have played the Steve McQueen role

Bill Simmons

Damian Lewis is miscast and does not capture McQueen.

Chris Ryan

Agrees the casting is off, though the role itself is small.

19 People discussedActors, directors, writers, and producers
very favorableBrad PittBill Simmons: Praised as the movie’s standout for a weathered, charismatic supporting performance that elevates Cliff Booth into one of his signature roles. About 8 min very favorableLeonardo DiCaprioChris Ryan: Described as astonishing, self-reflective, and perhaps giving his best performance, with Rick Dalton seen as a career-defining role. About 8 min very favorableQuentin TarantinoBill Simmons: Admired for writing a sentimental, memory-driven Hollywood fable and for his obsessive attention to detail in the production design and references. About 16 min favorableMargot RobbieBill Simmons: Discussed as intentionally limited in screen time because her character represents the bright beginning of a career rather than a plot-heavy arc. About 16 min favorableAl PacinoBill Simmons: Praised for a lively producer turn that helps trigger Rick’s career crisis and feels like a sequel-style performance. About 16 min
mixedBruce LeeChris Ryan: His scene is defended as a memory fantasy that reveals Cliff’s unreliability, though they acknowledge the scene’s controversy. About 24 min
very favorableSharon TateBill Simmons: Seen as the film’s moral center and a symbol of the career beginning that balances Rick’s decline. About 16 min
neutralRoman PolanskiBill Simmons: Mentioned mainly as part of Sharon Tate’s social world and the film’s historical backdrop. About 40 min · medium confidence
mixedSteve McQueenBill Simmons: Used as a comparison point for Tarantino’s alternate-history casting and criticized via the film’s portrayal and casting choice. About 48 min
criticalDamian LewisBill Simmons: Called miscast as Steve McQueen and one of the only elements the hosts dislike. About 48 min
favorableMargaret QualleyBill Simmons: Highlighted as a memorable breakout as Pussycat and a major Deion Waiters-style standout. About 56 min
favorableNicholas HammondChris Ryan: Praised for Sam Wanamaker’s energetic, expository, movie-nerd performance. About 56 min
favorableAustin ButlerBill Simmons: Mentioned as a strong supporting presence as Tex Watson and as a future star. About 56 min
favorableBruce DernChris Ryan: Defended as a solid casting choice for the ranch owner role, though the hosts note Burt Reynolds might have changed the feel. About 48 min
neutralBurt ReynoldsBill Simmons: Mentioned as the original choice for a role and as a useful historical parallel to Rick Dalton’s career path. About 48 min · medium confidencemixedJennifer LawrenceBill Simmons: Mentioned as a rejected early idea for Sharon Tate casting that the hosts doubt would have worked. About 56 min · medium confidenceneutralTom CruiseChris Ryan: Raised as a possible Cliff Booth type and as an actor Tarantino has wanted to work with. About 48 min · medium confidenceneutralWill SmithBill Simmons: Mentioned as the alternate lead Tarantino once considered for Django, in a broader discussion of star casting. About 1:04 · medium confidence
neutralLena DunhamBill Simmons: Cited as a stunt-casting surprise in the Manson family and an example of the film’s dense ensemble. About 32 min
12 Conversation takesSpeakers shown only where the transcript identifies them
Chris RyanLoved it

Brad Pitt

Argues Pitt’s Cliff Booth is a defining late-career role that suits his mature charisma and could become his signature part.

About 8 min
Bill SimmonsLoved it

Brad Pitt

Sees Pitt as the major revelation of the movie and as finally delivering the full character-actor package he always had in him.

About 8 min
Sean FennesseyLoved it

Leonardo DiCaprio

Calls DiCaprio’s Rick Dalton performance astonishing and arguably his best ever because it is twitchy, insecure, and self-reflective.

About 8 min
Bill SimmonsLiked it

Margot Robbie / Sharon Tate

Pushes back on criticism that the Sharon Tate material is too thin and says the point is to show the bright beginning of her career.

About 16 min
Chris RyanLiked it

Tarantino’s historical correction

Frames the movie as a memory piece and part of Tarantino’s larger project of rewriting history through imagination.

About 16 min
Bill SimmonsLoved it

Pacino at Musso and Frank’s

Treats the Musso & Frank’s sequence as classic, funny career advice and one of the film’s essential moments.

About 16 min
Chris RyanLoved it

Bruce Lee fight

Defends the scene as an unreliable-memory fantasy that reveals Cliff’s delusions rather than insulting Bruce Lee.

About 24 min
Bill SimmonsLoved it

Sharon Tate watching her movie

Says the sequence is a perfect expression of the film’s emotional design and Tate’s innocence.

About 24 min
Chris RyanLoved it

Rick’s trailer breakdown

Calls the trailer meltdown the movie’s funniest and most rewatchable sequence.

About 32 min
Bill SimmonsLiked it

Spahn Ranch

Praises the sequence’s horror tension, the dogs, and Cliff’s cool-headedness under pressure.

About 32 min
Sean FennesseyLoved it

1969 recreation

Admires the painstaking reconstruction of Los Angeles, noting how much signage and atmosphere had to be rebuilt.

About 40 min
Bill SimmonsLoved it

Quentin Tarantino

Frames Tarantino as obsessive, detail-locked, and uniquely capable of making a sentimental movie about Hollywood memory.

About 16 min
6 ThemesThe larger ideas in the discussion

Career rise and decline

The movie is framed as a study of one career beginning while another is ending, with Rick’s collapse contrasted against Sharon Tate’s ascent.

About 8 min

Memory and unreliability

The hosts treat several scenes as imagined or memory-driven, especially Cliff’s Bruce Lee fight and the movie’s broader historical rewrites.

About 16 min

Hollywood mythology and historical correction

They describe Tarantino as rewriting history to restore cowboy-hero fantasies and comment on his long-running project of correcting the record.

About 16 min

Sentimentality in Tarantino

The episode repeatedly notes that this is unusually sweet and sentimental for Tarantino, especially in its treatment of Tate.

About 16 min

Star power and late-prime acting

The discussion elevates Pitt and DiCaprio as performers whose late-career personas fit the film’s charisma-heavy roles.

Opening minutes

Production design and 1969 Hollywood recreation

They admire the painstaking reconstruction of Los Angeles, signage, clothing, and period atmosphere.

About 40 min
24 Facts and referencesProduction notes and other movies mentioned

Production note

The live podcast was recorded at Sundance before a small audience.

Opening minutes

Production note

Tarantino reportedly used 16 hours of KHJ radio broadcasts to reconstruct the era’s soundscape.

About 40 min

Production note

The Eros Theater scene is tied to the real New Beverly, which Tarantino owns.

About 1:04

Production note

The Maltese Falcon prop in the film belongs to Leonardo DiCaprio.

About 1:04

Production note

The same Cadillac from Reservoir Dogs appears in this film.

About 1:04

Production note

Tarantino allegedly wrote an extended novelization of Rick and Cliff’s lives before writing the screenplay.

About 1:04

Production note

The Bruce Lee fight is presented with a perspective shift that reveals the surrounding crowd disappearing.

About 24 min

Production note

The hosts say the movie did not open in China because Tarantino refused requested edits.

About 8 min · medium confidence

Mentioned with uncertainty

They repeatedly joke about a future 10th and final Tarantino film or even five episodes of Bounty Law.

Opening minutes · medium confidence

Heat

Used in a joke about Pacino’s supporting energy and as a reference point for all-time performances.

About 16 min

Moneyball

Used as an example of Pitt’s earlier transition into a calmer, older-screen persona.

About 8 min

Out of Sight

Cited as George Clooney’s best charisma movie.

About 8 min

Slap Shot

Mentioned as a model for older, beat-up charisma in Paul Newman’s career.

About 8 min

The Man from U.N.C.L.E.

Referenced in Pacino’s career-advice speech as one of the jobs Rick should move beyond.

About 16 min

Bounty Law

The fictional show in Rick Dalton’s career and a proposed Tarantino future project.

Opening minutes

Wanted Dead or Alive

Mentioned as the real series Bounty Law is based on.

About 16 min

Smokey and the Bandit

Used as an example of late-70s star vehicle charisma and Burt Reynolds-era fun.

About 16 min

True Romance

Referenced in the story about Tarantino’s inspiration for Sharon Tate watching her own movie.

About 24 min

Inglourious Basterds

Used as a precedent for Tarantino’s history-rewriting project.

About 16 min

The Irishman

Mentioned in connection with Pacino’s similar character energy and wig choices.

About 16 min

Reservoir Dogs

Referenced for the Cadillac and as part of Tarantino’s star-making track record.

About 1:04

Texas Chainsaw Massacre

Named as one of the visual and tonal influences on the Spahn Ranch sequence.

About 32 min

Apocalypse Now

Referenced as an influence on the Spahn Ranch sequence’s disorientation and menace.

About 32 min

Bob and Carol and Ted and Alice

Cited as another key Los Angeles influence on the film’s look and social atmosphere.

About 1:04
11 Running jokes and short linesRecurring bits captured from the conversation

Equinox / celebrity run-in jokes

Bill and Chris keep joking about seeing Leo or Pitt at Equinox and personalizing star encounters.

About 8 min

Fat Leo / Leo body comments

Repeated playful discussion of DiCaprio having a softer middle and how it fits the role.

About 8 min

Movie-nerd / fake-seen-it jokes

Bill jokes about pretending to have seen Oscar movies and lying about it.

About 8 min

Driving-around-in-LA bit

They repeatedly celebrate long car scenes and compare them to city driving now.

About 32 min

Altitude / live-show derailment jokes

Bill blames the Sundance altitude for his scattered bits and digressions.

About 16 min

Dog-as-character joke

The dog Brandy becomes a running gag, including whether the dog ever used the bathroom.

About 24 min

Bill Simmons

“I could be one pool party away”
About 1:04

Bill Simmons

“You're Rick fucking Dalton”
About 1:04

Chris Ryan

“That's your son? No, that's my stunt double”
Opening minutes

Bill Simmons

“I'm a has-been”
About 16 min

Bill Simmons

“I still got it”
About 1:04

MAKE IT A MOVIE NIGHT

Where to watch

UNITED STATES

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WHAT TO WATCH NEXT

Movies to watch before and after.

Three movies to watch before Once Upon a Time…in Hollywood, and three to watch next.

Finding six movies…Three to watch first and three to watch next.
Includes a Rewatchables episodePosters from TMDB.

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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