Leo nominated for Oscar

5 Times Leonardo DiCaprio Should Have Won the Oscar

It was clear early on that there was something special about Leonardo DiCaprio. He was nominated for his first Academy Award at the age of 20 for What’s Eating Gilbert Grape, and while the fresh-faced actor had already earned “teen heartthrob” status that would only grow when he reached the next level of fame, he was always keen on taking challenging roles rather than going for the flashy male lead. Indeed, films like The Basketball Diaries and This Boy’s Life aren’t exactly the kind of projects you take when you’re merely seeking superstardom, which is why signing on to star in James Cameron’s epic romance about the doomed Titanic was a fitting choice for the actor and, ironically, the one that launched him into the “movie star” realm.

DiCaprio’s craft would only blossom further when he made Gangs of New York and Catch Me If You Can back-to-back in the early 2000s, working with two of history’s greatest filmmakers and beginning an actor/director collaboration with Martin Scorsese that would result in the best performances of his career.

And yet, while we can all agree that DiCaprio is one of our finest performers, that little golden statue continues to elude him. With five nominations under his belt, DiCaprio is no stranger to the Oscar ceremony, but each time there seems to be some deciding hook, some other, more alluring narrative that inevitably leads to a DiCaprio loss.

With The Revenant, it looks like DiCaprio will finally be nabbing that elusive Oscar, and so now feels like as good a time as any to look back on five previous times the long overdue actor was deserving of a statue of his own.

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