After stints on TV shows like Growing Pains and Parenthood, DiCaprio made his big-screen debut alongside Robert De Niro. The teenager beat out hundreds of young actors and was handpicked by De Niro to play his stepson in the film.
At the age of 19, the actor was nominated for a best supporting actor Oscar for his portrayal of Arnie, a mentally disabled teen, opposite Johnny Depp.
"The script came along and I read it in one day and said yes the next day," DiCaprio said, of nabbing the role of a heroine-addicted teen in New York City, which was adapted from Jim Carroll's book of the same name.
Baz Luhrmann directed DiCaprio and Claire Danes in his modern retelling of Shakespeare's famous love tragedy. "He's one of the most interesting people I think I'll ever meet," Danes gushed of working with the actor.
The James Cameron film, which grossed over 1.8 billion dollars worldwide, made the actor, and his co-star, Kate Winslet, superstars. "You take things for granted, things like going to a museum … it's not as easy anymore," he said of his new-found celebrity.
After the massive success of Titanic, and his overwhelming international fame, DiCaprio was nominated for a worst actor Razzie Award in this Danny Boyle-directed film.
Frequent collaborator, Martin Scorsese, directed the actor for the first time alongside Daniel Day-Lewis and Cameron Diaz in this story of the settling of New York (which was nominated for 10 Oscars).
DiCaprio called his portrayal of Howard Hughes in his second Scorsese film (a role he'd been pursuing for years) "one of the most excited filming experiences I've ever had." The part earned him his second Oscar nomination.
The actor received his third Oscar nomination for his take on a Zimbabwean ex-mercenary caught up in Africa's conflict diamond trade.
"I feel like she's the best actress of her generation," DiCaprio said of working with Titanic co-star, Winslet, again.
DiCaprio partnered with Scorsese for the fourth time in this psychological thriller (for which he is now receiving awards buzz). "I knew that Leo…could pull this off and could hit certain levels of emotional and psychological depth," said the director.
"It's not often that the Hollywood studio system finances a film like this," Leonardo DiCaprio has said of his mind-bending summer blockbuster. "It's a testament to [director] Chris Nolan's imagination."
Inception was nominated for a Globe for best motion picture, drama.