Blood Diamond (2006)

I really wanted to include Basketball Diaries here or why not Once Upon a Time in Hollywood. Because he’s brilliant, of course, in both those films in the same way he is in Revolutionary Road, Titanic, Revenant, Catch Me if You Can and Romeo & Juliet. But it has to be Blood Diamond here, after all. Leo’s interpretation of the morally reprehensible diamond smuggler Danny Archer who struggles with equal parts excessive greed and his ability to sacrifice himself for the sake of someone else, the portion of his former life as a special forces soldier that he has tried to stifle for several years as a smuggler. DiCaprio does a brilliant job here and that includes a flawless South African accent as well as tons of presence and an ability to bring out the very best in co-stars Jennifer Conelly and Djimon Hounsou.

What’s Eating Gilbert Grape? (1993)

In Lasse Hallström’s finely tuned, fantastic adaptation of Peter Hedges’ equally phenomenal book (as we all know, of course), a 19-year-old, untrained and green DiCaprio portrays the mentally disabled little brother Arnie Grape with such conviction that I remember how, for a time, I was absolutely sure that he was actually mentally disabled – for real. Since Tropic Thunder, there has been a lot of talk about how actors like Sean Penn (I Am Sam) and Tom Hanks (Forest Gump) have gone too far in their interpretation of characters with some kind of developmental disability, and with hindsight, there is of course a lot in it. A 19-year-old Leo never fell into that trap, but instead did it with absolute bravura.
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Shutter Island (2010)

I remember wondering who on earth could do justice to the character of Teddy Daniels from Lehane’s eminent book, once it was turned into a film. I had hoped for Leo or Fassbender beforehand, but I don’t think I ever thought that either of them would be able to portray the mentally ill Daniels as well as DiCaprio did here. Layer upon layer upon layer is added to a nuanced and multifaceted exciting, gorgeous story about a man balancing on the verge of a complete nervous breakdown.

Django Unchained (2012)

There are certainly plenty of film villains more creepy and menacingly memorable than DiCaprio’s Calvin Candie. However, there are almost none that are as charismatic as they are genuinely loathsome, which has more to do with Leo’s performance than Tarantino’s (brilliant) script. Here Leo does one of his finest roles and it was, in retrospect, downright criminal that he was robbed of the Oscar for this fantastic role.

The Aviator (2004)

The way DiCaprio with nuance and subtlety portrays the aviation mogul and billionaire Howard Hughes in Scorsese’s fantastic biopic about this deeply fascinating man, must of course be applauded – So it stings the palms. Because it is his charismatic drive and ambition that is replaced by greed and paranoia during the course of the film that makes me as a viewer want to return, see more – read more about Hughes and try to understand more about how this remarkable man really worked. I think many biopics of this kind often fall into the trap of being a caricature of the person being portrayed, but not here. Not Hughes, and we have only Leo to thank for that.