After almost three decades of working in genre cinema, Quentin Tarantino reinvented his filmmaking style with 2019’s Once Upon a Time in Hollywood. Inspired by his own childhood memories of L.A. in the ‘60s, Once Upon a Time offers a gorgeous snapshot of a bygone era of both the film industry and the sun-drenched city where most of its operations take place.
The movie is filled with phenomenal performances by such contemporary movie stars as Leonardo DiCaprio, Brad Pitt, and Margot Robbie. If the movie had been made back in the ‘90s during Tarantino’s breakout phase, it might’ve starred Harrison Ford, Drew Barrymore, and Winona Ryder instead.
8 Harrison Ford As Rick Dalton
Leonardo DiCaprio gave one of the funniest and most nuanced performances of his career as Rick Dalton. This is a role that requires both leading-man looks and charisma and the dramatic chops to play Tarantino’s satirical takedown of Hollywood stars. In the ‘90s, Harrison Ford was leaving his own heyday behind, so he could’ve done a terrific job of playing Rick.
This would’ve been a great role for Ford to deconstruct his on-screen image playing cool-as-ice pulp heroes like Han Solo and Indiana Jones. The hilarious irony of Rick’s character is that he plays gallant, fearless heroes on-screen, but he’s an emotional wreck in real life.
7 Drew Barrymore As Sharon Tate
While her lack of dialogue was criticized, Margot Robbie’s Sharon Tate exists more as a symbol in Once Upon a Time in Hollywood. By showing the promising up-and-coming movie star in her day-to-day life, touching people’s lives, Once Upon a Time has ensured that Tate won’t just be defined by her murder in the history books.
In the ‘90s, Drew Barrymore was a perfect representation of Hollywood stardom. Barrymore shot to the top of the A-list with romantic comedies like Never Been Kissed and The Wedding Singer. Her fame was even used to create a Psycho-esque surprise in the opening scene of Scream.
6 Kirk Douglas As Marvin Schwarz
Marvin Schwarz is primarily an exposition tool in Once Upon a Time in Hollywood, but Al Pacino brought plenty of warmth and humor to humanize the role. Pacino’s legendary status as an actor helped to create a sense of Marvin’s deep knowledge of Old Hollywood and its tactics.
In the ‘90s, this role could’ve been played by a similarly legendary actor who’s been a renowned screen legend for even longer than Pacino: Kirk Douglas.
5 Jet Li As Bruce Lee
Mike Moh’s cameo appearance as Bruce Lee was one of the most controversial elements of Once Upon a Time in Hollywood. The movie paints Lee as brash and arrogant, and then he gets beaten up by a fictional stuntman, much to the chagrin of martial artists who hold the star of Enter the Dragon in high regard. But this scene takes place in Cliff’s mind as a recollection, and Tarantino’s novelization goes into greater detail about how he outwitted Lee and won the fight.
The role of Lee requires an actor with both dramatic abilities and martial arts prowess. In the ‘90s, Lee could’ve been played by Jet Li, who crossed over from acclaimed roles in Chinese cinema to Hollywood stardom with the role of the sadistic villain in Lethal Weapon 4.
4 Winona Ryder As Pussycat
Pussycat, played by Margaret Qualley, is the most prominent member of the Manson Family to be featured in Once Upon a Time in Hollywood. She isn’t based on any particular member of the real cult, but the character is speculated to be based on “Kitty Kat,” who was similarly sent into the city to lure men back to Spahn Ranch.
Winona Ryder could’ve played this role brilliantly in the ‘90s. Qualley played Pussycat’s blunt personality with the same kind of dry comedic sensibility that Ryder exhibited in Heathers and Beetlejuice.
3 Paul Newman As George Spahn
George Spahn only appears in one scene in Once Upon a Time in Hollywood, but that scene is the brilliantly anticlimactic payoff to the movie’s tensest, most suspenseful sequence, so it’s pretty important. According to The Hollywood Reporter, Burt Reynolds was initially cast in the role, but after his untimely passing, he was replaced by Tarantino regular Bruce Dern.
Reynolds and Dern share the status of screen legend. In the ‘90s, this part could’ve been filled by a screen legend whose stardom predates both of them: Paul Newman.
2 Mara Wilson As Trudi Frazer
Julia Butters gave one of the most revelatory performances in Once Upon a Time in Hollywood as Trudi Frazer, a prodigious, well-spoken child actor (in her own words, “actor, not actress, because the word ‘actress’ is nonsensical”).
In the ‘90s, this part might’ve gone to Mara Wilson. Throughout the decade, Wilson appeared in a bunch of hit movies: Matilda, Mrs. Doubtfire, Miracle on 34th Street – she starred in more movies than most of her adult peers. Wilson’s own reputation as a prolific, hard-working child actor would’ve fed into the character of Trudi.
1 Robert De Niro As Cliff Booth
After playing reckless hotheads in movies like Mean Streets and Raging Bull throughout the ‘70s and ‘80s, Robert De Niro settled into playing somber antiheroes with more foresight than Taxi Driver’s Travis Bickle in the ‘90s in movies like Goodfellas and Heat. In this era of his career, he could’ve made a fascinating casting choice for Rick Dalton’s stunt double Cliff Booth.
De Niro played a soldier in The Deer Hunter, a cold-blooded killer in Cape Fear, and a similarly chilled-out, softly spoken ex-con in Tarantino’s own Jackie Brown.
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