The incredibly successful career of Leonardo DiCaprio, 6-time Oscar nominee who finally won his first Academy Award today

Leonardo DiCaprio is one of the most recognised actors of his generation — if not the most — and he finally won his first Academy Award for Best Actor in The Revenant today.

The 41-year-old started acting in commercials when he was 14 and soon made his mark on TV shows.

The actor landed his first Oscar nomination when he was 19 and shot to superstardom, causing “Leo Mania” with his portrayal of Jack Dawson in “Titanic.” 

Since then, he’s earned a total of six nominations. His snubs have become a running joke among fans. Some have created “Sad Leo” memes, and one fan even created a computer game devoted to the subject.

But with his portrayal of Henry Glass in “The Revenant,” DiCaprio has finally snagged the elusive — and well-deserved — Oscar. 

Here’s a look back at his memorable career: 

Leonardo DiCaprio began his career acting in television ads, particularly after landing one for Matchbox cars when he was 14.

His first role was in the direct-to-video film 'Critters 3,' and he soon landed TV roles in the short-lived series 'Parenthood,' based on the movie of the same name, and other series including 'The New Lassie,' 'Santa Barbara,' and 'Roseanne.'

New Line Home Video
'Critters 3.'

He gained attention for his recurring role as a homeless kid in 'Growing Pains' during the sitcom's seventh and final season.


Soon after that, Robert De Niro handpicked DiCaprio to play the lead in 'This Boy's Life.' This was DiCaprio's big-screen debut.

Warner Bros. Pictures

But it was his next role starring as the developmentally disabled brother in 'What's Eating Gilbert Grape' that earned him critical praise and landed him his first Oscar nomination. He was 19.

Paramount Pictures

In 1995, he appeared in the Western 'The Quick and the Dead,' as French poet Arthur Rimbbaud in 'Total Eclipse,' and as a young drug addict in 'The Basketball Diaries.'

New Line Cinema
'The Basketball Diaries.'

He dove into romances with 'Romeo + Juliet,' Baz Luhrmann's 1996 modern take on Shakespeare's classic romantic tragedy.

20th Century Fox

It was his role as Jack Dawson in David Cameron's 'Titanic' that catapulted him to superstardom. The film is the second-highest grossing worldwide, but according to Cameron, DiCaprio needed some convincing to take the role. The director told People, 'Leo didn't trust me 100 per cent. Leo was questioning everything in the script... Then there was this cathartic moment when we both just sat in my trailer and talked for a couple of hours, and we hugged at the end and went back to work.'

20th Century Fox

DiCaprio tackled a few more roles, including 'The Man in the Iron Mask' and 'The Beach,' before landing the lead opposite Tom Hanks in Stephen Spielberg's 'Catch Me If You Can' and earning his third Golden Globe nomination.

'Catch Me If You Can'

That same year, he starred in 'Gangs of New York.' The film would mark DiCaprio's first collaboration with director Martin Scorsese.

Miramax Films

DiCaprio founded Appian Way Productions, and the company's first film was 2004's 'The Assassination of Richard Nixon.' The next was the 2004 biopic 'The Aviator,' starring DiCaprio.

Scorsese and DiCaprio teamed up again for 'The Aviator.' DiCaprio earned his first lead actor Oscar nomination (second total) for his portrayal of Howard Hughes. He won his first Golden Globe for the role.

Warner Bros.

In 2007, he narrated, cowrote, and coproduced 'The 11th Hour,' a documentary examining the state of the environment.

Warner Independent Pictures

'The Departed' in 2006 saw Scorsese and DiCaprio back together. The actor earned a Golden Globe nomination for his portrayal of a cop who infiltrates an organised crime organisation.

Warner Bros.
the departed

He earned another Golden Globe nomination for 'Blood Diamond' from that same year. His portrayal of a diamond smuggler landed him his third Oscar nomination.

Warner Bros.

He reunited with his 'Titanic' costar Kate Winslet for 2008's 'Revolutionary Road.' The film earned critical praise and garnered DiCaprio his seventh Golden Globe nomination.

Paramount Vantage

DiCaprio took on psychological films in 2010, appearing in Christopher Nolan's science-fiction thriller 'Inception'...

Warner Bros.

...and teaming up with Scorsese yet again for 'Shutter Island.'

He earned another Golden Globe nomination in 2012 for his portrayal of J. Edgar Hoover in Clint Eastwood's 'J. Edgar.'

Warner Bros.

DiCaprio took on an unusually villainous role in Quentin Tarantino's Oscar-winning Western 'Django Unchained,' and earned another Golden Globe nomination.

He worked with 'Romeo + Juliet' director Baz Luhrmann again for a new adaptation of F. Scott Fitzgerald's 'The Great Gatsby.'

Known for his close collaborations, he starred in Scorsese's 'The Wolf of Wall Street.' His portrayal of the exorbitant stockbroker Jordan Belfort earned him a Golden Globe win and fourth Oscar nomination. He was also nominated for an Oscar as a producer of the film. Following his role in the film, DiCaprio took a break from acting to spend his time 'doing good for the environment.'


During this acting break, he helped produce 'Virunga,' a Netflix documentary about the Virunga National Park rangers who risk their lives to protect the world's remaining mountain gorillas. He earned an Emmy nomination for the documentary.

A still from 'Virunga.'

This year, DiCaprio could finally earn his elusive Oscar for his depiction of Henry Glass in 'The Revenant.' The film has already earned him a Golden Globe, as well as his first BAFTA win (fourth nom) and first SAG Award.

Kimberley French/20th Century Fox

He may not have won Hollywood's most prized statuette yet, but a survey by Hollywood Reporter found he makes around $25 million per picture, which puts him in the big leagues with Robert Downey Jr.


In 2015, it was announced that DiCaprio and Scorsese would team for 'The Devil in the White City,' an adaptation of the nonfiction book of the same name. DiCaprio will be playing Dr. H. H. Holmes, a serial killer.

Mark Davis/Getty Images for SBIFF

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