Leonardo DiCaprio: Ranking Every Performance From Worst To Best
17. Jay Gatsby - The Great Gatsby
On paper, at least, we all presumably thought that Leonardo DiCaprio would make for the perfect Jay Gatsby - charming, handsome... but capable of getting across that inner turmoil, you know? So it probably came as a bit of a surprise when Leo turned out to be just an "all right" Gatsby - close, but no cigar, old sport. "Old sport" - like what Gatsby says in the book and everything. Anyhow, this falls in with that collection of Leo roles that are perfectly fine, but just aren't firing on all cylinders. Or maybe the movie was so bad that were just distracted by Baz Lurhman's questionable direction.
16. Amsterdam Vallon - Gangs Of New York
Gangs of New York marked the first time that Leonardo teamed with his friend and frequent collaborator Martin Scorsese, who decided that he wanted to make the actor into his late-stage Robert De Niro when that actor became more interested in stuff like Meet the Fockers. The results are somewhat mixed here, though - Leo shows promise, but he also feels far too boyish to play the thuggish Amsterdam Vallon, which certainly wasn't helped by the fact that he was acting across from, oh, DANIEL DAY-LEWIS. Seriously, what kind of raw deal was that, Marty?
15. Jim Carroll - The Basketball Diaries
The Basketball Diaries is not a great movie by any standard, but DiCaprio is pretty darn great in it and is enough of a reason to seek this one out, despite its obvious flaws. The Basketball Diaries is based on the real life memoirs of an actual guy named Jim Carroll, which is who DiCaprio plays so vividly here. As a promising teenage basketball player who develops an addiction to heroin, Leo's performance is raw, bold and nervy. As critic Peter Travers said at the time: "You leave the movie believing that Leonardo DiCaprio could do anything." He wasn't far off.
14. Romeo Montague - Romeo + Juliet
Well, of course he played Romeo once - look at him. All floppy-haired and wide-eyed - he's the perfect modern incarnation, surely? Just before Titanic, then, and before pretty much every female below the age of fifty fell madly in love with Jack Dawson, Baz Luhrmann plucked DiCaprio up and cast him as the lead in his adaptation of William Shakespeare's classic play. It's a good performance, purely because he doesn't play it too soppy, nor does he go too far with the whole "look, there's a cigarette dangling from my lip - isn't that cool?" side of things either.
