I remember sitting in the theater as the credits rolled on opening night of Martin Scorsese’s Shutter Island. As Max Richter’s "On the Nature of Daylight" played softly, my best friend and I sat in silence, quietly weeping to ourselves. And although the film was a wonderfully-shot journey of psychological thrill, it was Leonardo DiCaprio’s performance that moved us to tears. Did we have our own flair for the dramatic? Yes. But really, he was just so good we couldn’t help but succumb to our emphatic emotions.

But it’s always that way—no matter the film, in the twenty years that he’s been gracing our screens, Leo has never given a bad performance. Whether he’s playing a mentally-handicapped teenager coping with the strains of family, an infamous imposter conning his way around the world, a family man wrestling with the trials of love, or a psychopathic slave-owner, he always delivers a performance that’s brimming with conviction, intensity, charm, and agility—with that signature essence of Leo that lingers even when he disappears into his characters.

And this week, we’ll see him take on one of his most anticipated roles yet as the iconic role of Jay Gatsby in Baz Luhrmann’s lavish reimagining of F. Scott Fitzgerlad’s The Great Gatsby. So in honor of, what I am sure is to be another brilliant performance, here’s a look at some of Leo’s best roles throughout the years. And for good measure, a few old interviews with the young star before he went on to be Hollywood’s most beloved leading man. Enjoy.

The Aviator as Howard Hughes, 2004

What’s Eating Gilbert Grape as Arnie Grape, 1994 

DiCaprio, 1995

The Departed as Billy, 2007

DiCaprio, 1995

Gangs of New York as Amsterdam Vallon, 2002

Romeo + Juliet as Romeo, 1997

Django Unchained as Calvin Candie,  2013

DiCaprio, 1997

Marvin’s Room as Hank, 1996

Revolutionary Road as Frank Wheeler,  2009

Catch Me If You Can as Frank Abagnale Jr., 2003 

Behind the Scenes Rome + Juliet

Titanic as Jack Dawson, 1998 

Shutter Island as Teddy Daniels, 2010

The Basketball Diaries as Jim Carroll, 1995