Like many Quentin Tarantino movies, Once Upon a Time in Hollywood features a large cast that blends proven box-office darlings with stars on the verge of fame. The movie is a love letter to 1960s Los Angeles and the film industry centered on the meta casting of Leonardo DiCaprio as Rick Dalton, an actor whose career is fading, and Brad Pitt as Cliff Booth, Rick’s best friend and stunt double. Using two of the world’s biggest movie stars to comment on Hollywood is a classic Tarantino casting move.
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Many actors who cameoed as members of the Manson Family were just about to break out as major stars. Mikey Madison won an Oscar for her titular role in Anora, adding her to a list of relatively unknown actors at the time who are now marquee stars, including Austin Butler, Sydney Sweeney, and Margaret Qualley. Looking back on some of the best movies the Once Upon a Time in Hollywood cast has appeared in over the decades both before and after Tarantino’s movie makes me appreciate even the smaller cameos more.
You are watching: 12 Best Movies Starring The Once Upon A Time In Hollywood Cast
12
Immaculate (2024)
Sydney Sweeney As Sister Cecilia
Sydney Sweeney is best known for Euphoria and The White Lotus, but she has a small role as Snake, a member of the Manson Family, in Once Upon a Time in Hollywood. She later launched her own production company, Fifty-Fifty Films, and both starred in and produced Anyone but You. However, her biggest success as both a producer and actress came in 2024 with Immaculate, a psychological horror film.
Sweeney plays Immaculate‘s Cecilia, an American nun who arrives at an Italian convent only to uncover sinister secrets. Her gripping performance, combined with the film’s eerie atmosphere and shocking twists, made Immaculate a breakout hit. Both commercially successful and critically praised, the film solidified Sweeney as a legitimate box office star and a savvy producer capable of launching an original movie.
11
Do Revenge (2022)
Maya Hawke As Eleanor
Maya Hawke gained early recognition in her own right for Once Upon a Time in Hollywood in her brief but memorable role as Flowerchild, a hesitant member of the Manson Family. Stranger Things launched her stardom, but Do Revenge cemented Hawke as a movie lead. Netflix’s dark teen comedy became a viral hit, thanks to its sharp dialogue, stylish aesthetic, and Hawke’s magnetic performance as Eleanor, a queer outcast turned vengeful mastermind. Hawke’s chemistry with co-star Camila Mendes and the film’s twisty plot also fueled online discourse, making Do Revenge a cult favorite.
10
I Am Sam (2001)
Dakota Fanning As Lucy Diamond Dawson
I Am Sam is a poignant drama that explores themes of love, disability, and parental rights. The movie’s heart is Dakota Fanning’s remarkable performance as Lucy, the young daughter of a father with an intellectual disability, played by Sean Penn. At only seven years old, Fanning delivered a performance far beyond her years, earning critical acclaim and becoming the youngest Screen Actors Guild nominee in history.
Fanning’s casting in Once Upon a Time in Hollywood adds an extra layer of legacy to Tarantino’s film, as this partially marked the transition out of her era as a child star. Fanning took on an eerie, adult role as Manson Family member Squeaky Fromme, playing against type to surprise audiences.
9
The Substance (2024)
Margaret Qualley As Sue
The Substance was an unlikely Oscar contender — body horror films rarely break into major awards conversations. However, its sharp social commentary and powerhouse performances elevated it beyond genre constraints. The Substance‘s grotesque yet deeply emotional ending explores beauty, power, and identity, resonating with critics and audiences alike. Margaret Qualley delivered a fearless, career-defining performance, balancing raw vulnerability with unsettling intensity, even if she did not receive the same awards recognition as Demi Moore.
Qualley’s work in The Substance has solidified her as a leading actress, taking her career to the next level. This success traces back to Once Upon a Time in Hollywood, where her captivating turn as the enigmatic Manson girl, Pussycat, caught Hollywood’s attention. Qualley has used the breakout role to pursue bold, challenging projects like The Substance and Drive-Away Dolls.
8
Elvis (2022)
Austin Butler As Elvis Presley
Baz Luhrmann’s Elvis was both a critical and commercial triumph, driven by Austin Butler’s transformative performance. The movie is a bold reimagining of Elvis Presley’s life; Butler’s deep commitment to the role made it an electrifying experience and catapulted him beyond his teen heartthrob roots. His method acting was so intense that Butler retained Elvis’ voice long after filming wrapped, a testament to his dedication. However, his chilling turn as Tex Watson in Once Upon a Time in Hollywood proved he could handle serious, high-profile roles, paving the way for Elvis, Dune: Part Two, and more.
7
Escape From New York (1981)
Kurt Russell As Snake Plissken
Escape from New York is a quintessential 1980s action movie that transformed Kurt Russell from a Disney heartthrob to a gritty action star. Russell’s Snake Plissken — a cynical, eye-patched antihero navigating a dystopian Manhattan — helped redefine the action hero archetype, influencing films like The Road Warrior and Metal Gear Solid.
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The movie also showcased Russell’s ability to balance toughness with charisma, propelling him into a decades-long collaboration with John Carpenter. Russell was a symbol of old-school, rugged Hollywood by the time Tarantino cast him in Once Upon a Time in Hollywood, where his presence adds meta-textual weight, bridging the director’s love for ’70s and ’80s cinema with the film’s themes of industry change and fading stardom.
6
Anora (2024)
Mikey Madison As Anora “Ani” Mikheeva
Anora‘s dark humor, social realism, and unexpected emotional depth made it both an electrifying character study and a biting commentary on power, money, and survival. The movie was conceived by Sean Baker as the writer-director-editor, but it was Mikey Madison’s performance that brought the movie to life. As she is in nearly every frame of the movie, Madison’s role as Anora Mikheeva, a stripper who marries a Russian oligarch’s son, is synonymous with the movie itself.
Madison’s casting in Once Upon a Time in Hollywood as Manson Family member Susan “Sadie” Atkins marked her transition from television to film, allowing her to showcase her versatility and take on more adult roles than the teenager she played in Better Things.
5
Kill Bill: Volume 1 (2004)
Michael Madsen As Sidewinder/Budd
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Kill Bill is one of the most iconic films of all time due to its masterful blend of genres, kinetic action, and emotional depth. Tarantino’s love letter to samurai epics, spaghetti westerns, and grindhouse cinema delivers unforgettable visuals and fight choreography. Michael Madsen’s role as Budd, the washed-up, regretful brother of Bill, adds a melancholic weight to the revenge saga, revealing a different side to Tarantino’s usual villains.
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Kill Bill’s influence shaped Tarantino’s later work, refining his approach to nonlinear storytelling and genre-blending. By casting his longtime collaborator Madsen in Once Upon a Time in Hollywood, Tarantino reinforced his filmography’s interconnectivity, using Madsen’s presence to evoke the fading grit of Hollywood’s past.
4
Barbie (2023)
Margot Robbie As Stereotypical Barbie
Barbie was a cultural phenomenon, seamlessly blending spectacle with feminist commentary. Its success is inseparable from Margot Robbie’s performance, embodying Barbie’s evolution from an idealized doll to a self-aware woman with charm, humor, and emotional depth. As both star and producer, Robbie had been building to this moment, using her production company, LuckyChap, to champion bold, female-driven stories, including Promising Young Woman and I, Tonya.
Robbie was a star on the rise before Once Upon a Time in Hollywood, but she held her own alongside established legends DiCaprio and Pitt. Robbie’s role as Sharon Tate was controversial given its reimagining of tragic events. The movie symbolizes Tarantino’s reverence for Hollywood’s past, but Robbie herself was on the verge of redefining its future.
3
The Godfather (1972)
Al Pacino As Michael Corleone
The Godfather revolutionized storytelling with its operatic scope, complex characters, and masterful direction by Francis Ford Coppola. Most importantly, The Godfather elevated the crime genre, blending brutal violence with deep familial and moral themes, influencing everything from Goodfellas to Breaking Bad. Al Pacino’s portrayal of Michael Corleone transformed him from an unknown actor into a cinematic titan; a defining figure in movie history. By casting Pacino in Once Upon a Time in Hollywood, Tarantino honored a Hollywood legend. His role as Marvin Schwarz, a seasoned agent, carries more meta significance — an icon of ’70s cinema guiding a fading star of that era.
2
Se7en (1995)
Brad Pitt As Detective David Mills
Se7en is a masterclass in psychological horror and neo-noir, redefining the serial killer genre with its bleak atmosphere, shocking ending, and David Fincher’s meticulous direction. Its oppressive tone, rain-drenched aesthetic, and methodical pacing influenced countless films, from Zodiac to Prisoners. Brad Pitt’s role as Detective David Mills, a hotheaded idealist whose worldview is shattered, showcased his dramatic range beyond his early heartthrob status.
The movie proved Pitt could carry serious, gritty roles, leading to a career that balanced prestige projects with blockbuster appeal, like Fight Club. Pitt brings effortless cool and old-school masculinity to stuntman Cliff Booth in Once Upon a Time in Hollywood, reinforcing Tarantino’s vision of a declining yet fiercely resilient Hollywood.
1
Titanic (1997)
Leonardo DiCaprio As Jack Dawson
Titanic remains one of the most iconic movies in history, seamlessly blending grand romance with historical tragedy to captivate audiences worldwide. James Cameron’s groundbreaking visual effects and emotional storytelling cemented his legacy. Meanwhile, Leonardo DiCaprio’s role as Jack Dawson propelled him from teen heartthrob to global superstar.
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DiCaprio’s charm, vulnerability, and effortless chemistry with Kate Winslet made Jack unforgettable, but DiCaprio was determined not to be typecast. After Titanic, he pivoted to challenging, auteur-driven films like The Aviator and The Wolf of Wall Street. In Once Upon a Time in Hollywood, DiCaprio’s casting as Rick Dalton was a flawless choice, as DiCaprio, now an industry veteran, embodied an actor desperate to stay relevant in a changing Hollywood.
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Once Upon a Time in Hollywood
R
Comedy
Drama
8/10
11
9.4/10
Release Date
July 26, 2019
Runtime
159 minutes
Director
Quentin Tarantino
Writers
Quentin Tarantino
Cast
See All
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Tim Roth
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Margot Robbie
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Category: Entertainment