Here Are All The Times Leonardo DiCaprio Did NOT Win An Oscar

Over the last 20 years, Leonardo DiCaprio has cultivated his acting career and become one of the most famous men alive. He’s revered by most, yet he’s never won an Oscar. It’s fast become a bit of a thing when Leo isn’t nominated/doesn’t win an Oscar. The internet basically explodes every time he loses. The fans want him to win. After winning the Golden Globe for The Revenant, people are starting to wonder…will 2016 be Leo’s year? All signs seem to point to yes, but we will NEVER know.

1994What’s Eating Gilbert Grape


Nominated For: Best Supporting Actor

Who He Lost To: Tommy Lee Jones for The Fugitive

While we will always say that playing Arnie Grape in What’s Eating Gilbert Grape is one of Leonardo DiCaprio’s greatest roles ever, we can understand his loss that year…but not to Tommy Lee Jones. Tommy is great, don’t get us wrong, The Fugitive is also great. But the award for Best Supporting Actor in 1994 should have actually gone to Ralph Fiennes for playing the depraved Amon Goeth in Schindler’s List.

2006 – The Aviator


Nominated For: Best Actor

Who He Lost To: Phillip Seymour Hoffman for Capote

2006 was not going to be Leo’s year, I think everyone knew that after seeing the nominees. If Phillip didn’t win for his stellar Performance in Capote, the Oscar surely wouldn’t have gone to Leo. Heath Ledger had been nominated for Brokeback Mountain, as well as Joaquin Phoenix for Walk The Line. 2006 was some stiff competition for poor Leo, we understand why he was passed over that year.

2007 – Blood Diamond


Nominated For: Best Actor

Who He Lost To: Forest Whitaker for The Last King of Scotland

2007 was another stiff competition year. If Forest Whitaker hadn’t taken the gold statue home that night, most of us weren’t rooting for Leo once more. We all were a little heartbroken that year when Will Smith didn’t win for his biopic The Pursuit of Happyness. Leo left empty handed once again and had to return, hoping to be nominated another day!

2014 – The Wolf of Wall Street


Nominated For: Best Actor

Who He Lost To: Matthew McConaughey for Dallas Buyers Club

It seems that fate is never in Leo’s hands, because every nomination he receives, happens the same year that someone who was just a bit better was also nominated. We don’t always agree with who wins, but we can certainly agree when nominated against Matthew for Dallas Buyers Club, Bruce Dern for Nebraska, and Chiwetel Ejiofor for 12 Years A Slave that Leo didn’t deserve to win that year.

Movies Leo Was NOT Even Nominated For:

What really must sting is the fact that while Leo never seems to win an Oscar, there are too many times he’s been looked over when nominations are rolled out. Not every movie he’s ever done deserves an Oscar nom, but he’s been in a lot of critically acclaimed films, as well as pictures that were LOVED by the fans. We’re not sure which is worse, getting nominated and not winning or not getting nominated at all.

1995 – The Basketball Diaries

1997 – Titanic


Leo was basically the only person not to get nominated for his work in Titanic (even though he’s 99% of the reason anyone still watchs it). Titanic was nominated for 15 Oscars, including Best Actress for Kate Winslet, Best Supporting Actress for Gloria Stuart, and Best Director for James Cameron. Leo was ROBBED. They let Jack sink!

1998 – The Man In The Iron Mask

2002 – Gangs of New York

2002 – Catch Me If You Can


Once again, Leo was passed over at the Oscars in favor of his on-screen counterparts. At the 75th Academy Awards, Christopher Walken (who portrayed Frank Abagnale Sr.) and John Williams were nominated for Best Supporting Actor and Best Original Score.

2006 – The Departed

2012 – Django Unchained


Django Unchained was nominated for 5 Oscars, but one of those was not for Leo. While he was pretty great at playing the terrible Calvin Candie, we understand why Christoph Waltz was nominated and won for Best Supporting Actor. Leo can’t be too upset about this one that, poor Jamie Foxx wasn’t even nominated for Best Actor nor was Quentin Tarantino nominated for Best Director.

2010 – Shutter Island

2010 – Inception

2013 – The Great Gatsby