This one is going to be a mighty difficult decision. Leo has so many fantastic performances in some fantastic movies, so picking a top 5 is tough. I want to make it clear that this is not the list of my favourite of his movies, its my favourite of his acting performances.
Honourable Mentions: This Boy's Life, Titanic, Romeo + Juliet, The Man in the Iron Mask, Gangs of New York, Catch Me If You Can, Blood Diamond, Body of Lies, Revolutionary Road, Shutter Island, Inception, J. Edgar, The Great Gatsby.
5.) The Departed
This first on this list of a team up between Leo and Martin Scorsese, and a fantastic example of the magic that comes when the two come together. Marty is obviously known for his gangster films thanks to Goodfellas for example, but the departed holds it's own in that category as well. Fantastic classic story of the spy within a highly organized organization, only this time the organizations have spies in both. Some other actors that appear in the film include Matt Damon, Jack Nicholson, Mark Whalberg, Martin Sheen, Alex Baldwin, and Vera Farmiga. It has an 8.5/10 rating on IMDB and is #49 on its Top 250 Films list, and 92%(critics) and 94%(audience) on Rotten Tomatoes. It was nominated for 5 Oscars winning 4 including Best Film Editing, Best Adapted Screenplay, Best Director for Martin Scorsese and Best Picture.
4.) The Wolf of Wall Street
This film was released in the fall and was one of the front runners in the Best Picture race. This movie was crazy, and the intensity was over the top, but it worked so incredibly well. If you enjoy movies with a lot of cocaine and hookers, this ones for you. The film was great at showing the downside to money, but its also pretty hilarious, which I think was probably necessary to making this film a success. If they had it just as a drama the intensity probably would have been too much. The fact that it is a true story is mind-blowing, because some of the things that happen are completely unbelievable. Other actors in the film included Jonah Hill, Margot Robbie, Matthew McConaughey, Rob Reiner, and Kyle Chandler. It has an 8.4/10 rating on IMDB and is #83 on the Top 250 Films list, and has a 77%(critics) and 84%(audience) rating on Rotten Tomatoes. The film was nominated for 5 Oscars including Best Actor, Best Supporting Actor, and Best Picture, sadly it won none of them.
3.) Django Unchained
I LOVE this movie. It topped my list of best films of 2012 last year and it my favourite Tarantino film. That acting was fantastic all around and even though I was happy that Christoph Waltz won the oscar for Best Supporting Actor in 2013, I thought Leo was robbed of at least a nomination. His performance was fantastic and it was so interesting to see him working with a director like Quentin Tarantino who is clearly so different from Martin Scorsese. Some other actors, besides Leo and Christoph Waltz, that were in the film were Jamie Foxx, Samuel L. Jackson, Kerry Washington, and many more. It was nominated for 5 Oscars, winning 2 for Best Supporting Actor for Christoph Waltz and Best Original Screenplay for Quentin Tarantino. The film has an 8.5/10 rating on IMDB and is #51 on its Top 250 Films list and has a 88%(critics) and 92%(audience) on Rotten Tomatoes.
2.) What's Eating Gilbert Grape
Its been a LONG time since I saw this film so its tough for me to remember a lot of detail, however, one thing I do remember is a young Leonardo DiCaprio's performance. I feel a little bad for Johnny Depp in this film because even though Leo was only a supporting role, it is his performance that stands out for just about everyone who has seen the film. The film follows Gilbert Grape, a young man who has to care for his disabled brother, Arnie, and his morbidly obese mother, and is faced with some tough decisions when he finds love. Besides Leo and Johnny we also see Juliette Lewis, John C. Reilly, and Crispin Glover. It was nominated for 1 Oscar for Best Supporting Actor for Leo, but sadly he did not win. It has a 7.8/10 rating on IMDB and 89%(critics and audience) rating on Rotten Tomatoes.
1.) The Aviator
Another great example of a fantastic collaboration between Leo and Martin Scorsese. The fact that he did not win the Oscar for Best Actor for his role as Howard Hughes in this film blows my mind. The film is incredibly interesting, and I knew nothing about Hughes, even though he was so incredibly eccentric. The film follows his personal life and career between the 1920s to the 1940s, including his battle with obsessive compulsive disorder, leading to a mental breakdown. Some of the other actors involved in the film include Cate Blanchett(who plays Katharine Hepburn), Kate Beckinsale, John C. Reilly, Alec Baldwin, Alan Alda, Ian Holm, Danny Huston, Jude Law, Gwen Stefani, and Adam Scott. It was nominated for 11 Oscars winning 5 for Best Supporting Actress for Cate Blanchett, Best Cinematography for Robert Richardson, Best Film Editing, Best Art Direction, and Best Costume Design. It has a 7.5/10 rating on IMDB and 87%(critics), 79%(audience) on Rotten Tomatoes.Honourable Mentions: This Boy's Life, Titanic, Romeo + Juliet, The Man in the Iron Mask, Gangs of New York, Catch Me If You Can, Blood Diamond, Body of Lies, Revolutionary Road, Shutter Island, Inception, J. Edgar, The Great Gatsby.
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