Citizen Kane (1941) - Directed by Orson Welles, widely regarded as one of the greatest films ever made, but lost Best Picture to "How Green Was My Valley."
Alfred Hitchcock - The acclaimed director never won an Oscar for Best Director despite multiple nominations for films like "Psycho," "Rear Window," and "Vertigo."
Stanley Kubrick - Despite his iconic status in cinema, Kubrick only won one Oscar for Best Visual Effects, and none for Best Director despite nominations for films like "2001: A Space Odyssey" and "A Clockwork Orange."
"Saving Private Ryan" (1998) - Steven Spielberg's war epic, often considered one of the greatest war films ever made, lost the Best Picture Oscar to "Shakespeare in Love."
Leonardo DiCaprio - Despite numerous acclaimed performances, DiCaprio only won his first Oscar for acting in 2016 for "The Revenant," after multiple nominations.
"Brokeback Mountain" (2005) - Ang Lee's groundbreaking film about a love affair between two cowboys lost the Best Picture Oscar to "Crash," a decision widely criticized.
"Do the Right Thing" (1989) - Spike Lee's powerful film about racial tensions in New York City was not nominated for Best Picture, despite its significant impact and critical acclaim.
"La La Land" (2016) - The musical was mistakenly announced as the Best Picture winner instead of "Moonlight," leading to one of the most memorable moments in Oscar history.