Leonardo DiCaprio & Brad Pitt’s ‘Once Upon A Time In Hollywood’ Helped Launch ‘Anora’ Star Mikey Madison!

Mikey Madison In Anora
Mikey Madison In Anora (Photo Credit – Instagram)

The 2025 Academy Awards concluded with a flourish, etching legacies aplenty, yet none rang out as resoundingly as the glistening indie romantic comedy-drama Anora, which commandeered five statuettes — Best Picture to Best Director, the night’s most vaunted haul.

Sean Baker, Anora’s multihyphenate helmsman, made history with four individual wins, a cataclysmic feat to surmount, but the spotlight also enunciated Mikey Madison taking home the Academy Award for Best Actress at 25. Madison’s outing as the salacious stripper Anora beguiled audiences, but did you know the actress first sauntered onto the big screen wielding a knife in a frenzied bid to attack Brad Pitt’s own Oscar-winning portrayal of Cliff Booth?

In the 2019 period romp Once Upon a Time in Hollywood, directed by Quentin Tarantino who years later would present Baker with his Best Director trophy, a teenage Madison embodied the eccentric Susan “Sadie” Atkins, one of the many acolytes of Charles Manson who — in reality and not the film — slew Roman Polanski’s eight-month-pregnant wife and actress, Sharon Tate, and her friend, hairstylist Jay Sebring, in 1969.

Unlike the grounded scale of Anora, that glistening ode to Hollywood’s golden age flaunted a roster of Pitt, Leonardo DiCaprio, Margot Robbie, Al Pacino, and more, whose liaisons elevated its grandeur, alongside the younger figures who later galvanized the 97th Oscars’ Best Picture race. These include Madison, Margaret Qualley (The Substance) and Austin Butler (Dune: Part Two), whose efforts elevated the 1969-set tale.

Like Anora, Once Upon a Time in Hollywood garnered a myriad of nods and clinched Pitt Best Supporting Actor and Best Production Design at the Academy Awards. A summer juggernaut, it also accrued $392 million worldwide against a $90 million budget. And evidently, Madison’s fleeting appearance there fueled her rise. The Anora star soon manifested her penchant for volatile roles as Amber Freeman in 2022’s Scream — second consecutive film where her character is set on fire.

Sean Baker, struck by Madison’s unapologetically violent turns in Tarantino’s opus and the dark yet comedic tone in the slasher installment, took an unorthodox path to formulate a mere synopsis, which he pitched to Madison. It was only after her affirmation did The Florida Project director flesh out the tragicomedy tale, a gamble that was actualized as Anora and precipitated both of them Oscar gold.

Reminding viewers of Tarantino’s gritty and raw dialogue-drenched flair, as well as Pretty Woman’s bourgeois gloss and Uncut Gems’ rush, Anora spun a maelstrom of a saga which witnesses Madison’s titular stripper striking an exclusive deal with Russian oligarch Vanya, a bond that deepens until his family and a group of Armenian goons meddle. As solicitation spirals into vehement shrieks, a chaotic bid to undo the actions of its young adult couple ensues.

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