Marilyn Monroe’s Last Great Role: Inside Some Like It Hot

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Released in 1959, Some Like It Hot is widely regarded as one of the greatest comedies in American cinema. Starring Marilyn Monroe, Tony Curtis, and Jack Lemmon, the film’s blend of sharp wit, gender-bending disguises, and daring themes made it both a box-office hit and a critical darling. But behind the laughs lies a story of creative brilliance, personal struggle, and a performance from Monroe that, while legendary, came at a high personal cost.

Set during the Prohibition era, Some Like It Hot follows two struggling musicians, Joe (Tony Curtis) and Jerry (Jack Lemmon), who accidentally witness the St. Valentine’s Day Massacre. In order to escape the mob, they disguise themselves as women and join an all-female band headed to Florida.

There, they meet Sugar Kane Kowalczyk (Marilyn Monroe), a ukulele player with dreams of marrying a millionaire. As Joe pretends to be a wealthy man to woo Sugar, and Jerry is courted by a real millionaire, the story spirals into a hilarious series of complications.

The film’s themes were considered risqué for the time. The cross-dressing, sexual innuendo, and even hints at homosexuality were bold moves in an era when Hollywood was still governed by the restrictive Hays Code. Director Billy Wilder, known for his sharp scripts and irreverent tone, pushed boundaries in ways that were subtle but unmistakably groundbreaking.

From the beginning, Billy Wilder knew he wanted Marilyn Monroe for the role of Sugar Kane. She was already a star, known for her performances in Gentlemen Prefer Blondes and The Seven Year Itch—also directed by Wilder. Despite previous friction between the actress and the director, Wilder believed no one else could bring the same vulnerability, sensuality, and comedic timing to the role.

Monroe, however, was at a turbulent point in her life. By 1958, she had married playwright Arthur Miller and moved to New York to study acting with Lee Strasberg at the Actors Studio. Monroe was trying to reinvent herself as a serious actress, and returning to Hollywood for a comedy didn’t align with those ambitions. Yet she took the role—perhaps out of obligation, financial necessity, or hope that it would cement her status as a true leading lady.

Filming Some Like It Hot was famously difficult. Monroe’s insecurities and dependence on pills made her unpredictable. She often arrived hours late to set, struggled to remember lines, and required dozens of takes for simple scenes. One of the most infamous examples was the scene where she opens a drawer and says, “Where’s the bourbon?”—a line she reportedly needed over 40 takes to deliver correctly.

Tony Curtis later remarked that kissing Monroe was “like kissing Hitler”—a comment he later claimed was a joke taken out of context, but one that reflected the tense atmosphere on set. Jack Lemmon, on the other hand, was more diplomatic, praising Monroe’s talent while acknowledging the challenges of working with her.

Despite the tension, Monroe’s performance was magnetic. She brought depth and charm to Sugar Kane, making her more than just a ditzy blonde. Beneath the flirtatious surface was a woman tired of being used, who longed for love and security. This emotional layer elevated the character and resonated deeply with audiences.

Upon its release, Some Like It Hot was an instant success. It earned over $25 million at the box office, a huge sum at the time. Critics praised its witty script, clever direction, and memorable performances. The film received six Academy Award nominations, including Best Actor (Jack Lemmon), Best Director (Billy Wilder), and Best Adapted Screenplay. It won one Oscar—for Best Costume Design, thanks to the stylish black-and-white outfits created by Orry-Kelly.

Interestingly, Wilder chose to shoot the film in black-and-white rather than color, despite Monroe’s contract specifying color film. The decision was made to make the male leads’ makeup more convincing when dressed as women—a choice that ultimately added a timeless charm to the film’s look.

In 2000, the American Film Institute named Some Like It Hot the greatest American comedy of all time. It also holds a prominent place in LGBTQ+ film history due to its playful take on gender and identity—particularly the iconic final line, “Nobody’s perfect,” delivered by Joe E. Brown in response to Jerry’s (in drag) confession that he’s a man.

For Monroe, Some Like It Hot was one of her last great roles. Just three years later, she would die tragically at the age of 36. Though the film was a triumph, it exposed the growing toll fame had taken on her health and mental state. Yet despite the behind-the-scenes chaos, Monroe’s star power shined through. Her performance remains a testament to her comedic timing, screen presence, and unique ability to embody fragility and allure at once.

In retrospect, Some Like It Hot is not just a comedy—it’s a cultural milestone. And Marilyn Monroe, amid her personal demons, gave one of her most unforgettable performances, proving once again that while some like it hot, Monroe made it iconic.

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