Leonardo DiCaprio’s Oscar Heartbreaks: 5 Performances That Almost Won Him An Academy Award
Before finally winning for The Revenant, Leonardo DiCaprio delivered several powerhouse performances that came heartbreakingly close to earning him an acting Oscar.
Leonardo DiCaprio’s Oscar Nominations (Photo Credit – Instagram)
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Leonardo DiCaprio is one of the most versatile and celebrated actors in Hollywood, known for delivering unforgettable performances across a wide range of genres. From James Cameron’s blockbuster Titanic to Christopher Nolan’s mind-bending Inception and, most recently, One Battle After Another, his filmography has been nothing short of stellar.
However, the film that finally earned him his first Best Actor Oscar was Alejandro González Iñárritu’s The Revenant (2015). Besides starring in this gripping survival drama, Leonardo DiCaprio came heartbreakingly close to winning an acting Oscar for five remarkable performances. Here’s a look at those films for which he was nominated but couldn’t win, and where you can stream them online today.
1. What’s Eating Gilbert Grape (1993)
Director: Lasse Hallström
IMDb Rating: 7.7/10
Streaming On: Amazon Video & Apple TV – Rent (U.S.)
Nomination Category: Best Supporting Actor
Plot: The coming-of-age drama follows Gilbert (Johnny Depp), a young man stuck in a small town, caring for his mentally challenged brother, Arnie (Leonardo DiCaprio), and their mother. His life changes when he meets Becky, a free-spirited traveler who helps him rediscover hope and happiness.
Plot: The film tells the story of Howard Hughes (Leonardo DiCaprio), a brilliant but troubled filmmaker and aviation pioneer. As he builds his empire, his success is shadowed by obsessive-compulsive disorder and growing paranoia.
3. Blood Diamond (2006)
Director: Edward Zwick
IMDb Rating: 8/10
Streaming On: Prime Video (India); Amazon Video & Apple TV – Rent (U.S.)
Nomination Category: Best Actor
Plot: This political thriller follows a smuggler (Leonardo DiCaprio) and a fisherman (Djimon Hounsou) in war-torn Sierra Leone whose lives intersect over a rare pink diamond. Their dangerous quest reveals the harsh truth behind the blood diamond trade.
4. The Wolf of Wall Street (2013)
Director: Martin Scorsese
IMDb Rating: 8.2/10
Streaming On: Lionsgate Play (India); MGM+ (U.S.)
Nomination Category: Best Actor
Plot: The dark comedy crime drama follows Jordan Belfort (Leonardo DiCaprio), a young stockbroker who amasses huge wealth through shady deals. His fortune leads to a wild and extravagant lifestyle, but as his schemes spiral out of control, the FBI begins to investigate, and his world starts to fall apart.
5. Once Upon a Time in Hollywood (2019)
Director: Quentin Tarantino
IMDb Rating: 7.6/10
Streaming On: Netflix & SonyLIV (India); Amazon Video – Rent (U.S.)
Nomination Category: Best Actor
Plot: Set in 1969, the period comedy-drama follows the story of a once-famous television actor, Rick Dalton (played by Leonardo DiCaprio), who has a tough time finding meaningful work in an evolving Hollywood. Along with his close friend and long-time stunt double Cliff Booth (played by Brad Pitt), he tries his best to stay afloat.
