Like many Quentin Tarantino movies,Once Upon a Time in Hollywoodfeatures 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 ofLeonardo 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.
Manyactors who cameoed as members of the Manson Familywere just about to break out as major stars.Mikey Madison won an Oscar for her titular role inAnora, 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 theOnce Upon a Time in Hollywoodcast has appeared in over the decades both before and after Tarantino’s movie makes me appreciate even the smaller cameos more.
12Immaculate (2024)
Sydney Sweeney As Sister Cecilia
Sydney Sweeney is best known forEuphoriaandThe White Lotus, but she has a small role as Snake, a member of the Manson Family, inOnce Upon a Time in Hollywood.She later launched her own production company, Fifty-Fifty Films,and both starred in and producedAnyone but You. However, her biggest success as both a producer and actress came in 2024 withImmaculate, a psychological horror film.
Her gripping performance, combined with the film’s eerie atmosphere and shocking twists, madeImmaculatea breakout hit.
Sweeney playsImmaculate’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, madeImmaculatea 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.
11Do Revenge (2022)
Maya Hawke As Eleanor
Maya Hawke gained early recognition in her own right forOnce Upon a Time in Hollywoodin her brief but memorable role as Flowerchild, a hesitant member of the Manson Family.Stranger Thingslaunched her stardom, butDo Revengecemented Hawke as a movie lead.
Netflix’s Do Revenge: 10 Main Characters, Ranked By Likability
Even though the characters in Do Revenge make some questionable choices, some of them are justifiable, meaning the villain can be the fan favorite.
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, makingDo Revengea cult favorite.
10I Am Sam (2001)
Dakota Fanning As Lucy Diamond Dawson
I Am Samis 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 inOnce Upon a Time in Hollywoodadds 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 asManson Family member Squeaky Fromme, playing against type to surprise audiences.
9The Substance (2024)
Margaret Qualley As Sue
The Substancewas 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 endingexplores 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 inThe Substancehas solidified her as a leading actress, taking her career to the next level.
This success traces back toOnce Upon a Time in Hollywood, where her captivating turn as the enigmaticManson girl, Pussycat, caught Hollywood’s attention. Qualley has used the breakout role to pursue bold, challenging projects likeThe SubstanceandDrive-Away Dolls.
8Elvis (2022)
Austin Butler As Elvis Presley
Baz Luhrmann’sElviswas 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 thatButler retained Elvis' voicelong after filming wrapped, a testament to his dedication.However, his chilling turn asTex Watson inOnce Upon a Time in Hollywoodproved he could handle serious, high-profile roles, paving the way forElvis,Dune: Part Two, and more.
7Escape From New York (1981)
Kurt Russell As Snake Plissken
Escape from New Yorkis 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 likeThe Road WarriorandMetal Gear Solid.
The Escape From New York Remake Faces An Impossible Recasting Challenge
The Escape From New York remake is finally happening, but in replacing Kurt Russell as Snake Plissken it faces a tough recasting challenge.
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 inOnce 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.
6Anora (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 AnoraMikheeva, a stripper who marries a Russian oligarch’s son, is synonymous with the movie itself.
Madison’s casting inOnce Upon a Time in Hollywoodas 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 inBetter Things.
5Kill Bill: Volume 1 (2004)
Michael Madsen As Sidewinder/Budd
Kill Billis 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.
Kill Bill Complete Timeline Explained
Kill Bill is a prime example of Quentin Tarantino’s signature nonlinear storytelling. Arranged in chronological order, it’s a different movie.
Kill Bill’s influence shaped Tarantino’s later work, refining his approach to nonlinear storytelling and genre-blending.By casting his longtime collaborator Madsen inOnce Upon a Time in Hollywood, Tarantino reinforced his filmography’s interconnectivity, using Madsen’s presence to evoke the fading grit of Hollywood’s past.
4Barbie (2023)
Margot Robbie As Stereotypical Barbie
Barbiewas 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, includingPromising Young WomanandI, Tonya.
The movie symbolizes Tarantino’s reverence for Hollywood’s past, but Robbie herself was on the verge of redefining its future.
Robbie was a star on the rise beforeOnce Upon a Time in Hollywood,but she held her own alongside established legends DiCaprio and Pitt.Robbie’s role as Sharon Tate was controversialgiven 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.
3The Godfather (1972)
Al Pacino As Michael Corleone
The Godfatherrevolutionized storytelling with its operatic scope, complex characters,and masterful direction by Francis Ford Coppola. Most importantly,The Godfatherelevated the crime genre, blending brutal violence with deep familial and moral themes, influencing everything fromGoodfellastoBreaking 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 inOnce 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.
