Some Like It Hot (1959), directed by Billy Wilder and starring Marilyn Monroe, Tony Curtis, and Jack Lemmon, follows two musicians who witness a mob murder and go on the run disguised as women in an all-female jazz band — where one falls in love with Monroe's Sugar Kane and the other is pursued by an elderly millionaire.

Why It Matters

• Voted the greatest comedy film ever made in the American Film Institute's 100 Years...100 Laughs poll
• Jack Lemmon's performance is a masterwork of physical comedy and comic timing
• The final line — Well, nobody's perfect — may be the single greatest closing line in film history

Made in black and white because Wilder felt Monroe's complexion looked green on color film, the movie navigates gender-bending themes that were genuinely transgressive for 1959 while being absolutely, relentlessly hilarious throughout.

Reference:

Wikipedia: Some Like It Hot

https://en.wikipedia.org/wiki/Some_Like_It_Hot