The Amazing Evolution of Leonardo DiCaprio in Famous Hollywood Movies

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Hands down, Leonardo DiCaprio is one of the most versatile actors in Hollywood today. And over the course of his career has had the opportunity to play characters from all over the map. Since becoming a household name in the mid nineties, the actor’s work has only gotten better. So it feels like now is the right time to take a look at The Amazing Evolution of Leonardo DiCaprio in Famous Hollywood Movies.

After playing a series of minor parts on the small screen, DiCaprio really got the audience’s attention for the first time with his performance in 1993’s Whats Eating Gilbert Grape. The actor took on the role of Arnie, and played the younger brother to Johnny Depp’s titular character. Viewers were blown away by DiCaprio’s convincing portrayal, and at the age of 19, was nominated for an Oscar because of it. In the big scheme of things, the movie isn’t the highest grossing of his career, but it might be the most important.

After the entertainment bigwigs started to take notice of the talented young actor, Leo did what 99% of actors do: Shakespeare. And what great actor doesn’t have a little Shakespeare in their background? In 1996, he was cast as the lead in Baz Luhrmann’s modern take on Romeo + Juliet. Working opposite Claire Danes, the film is a total audiovisual trip. The main obstacle people run into when reading William Shakespeare’s works is the language structure. And while the original dialogue remains intact, the contemporary setting bridged the gap. Making this one of the most accessible versions of the story, even if the contrast seems jarring. As a result of it’s approachability, the movie was a big hit with audiences. And suddenly people became a lot more interested in what DiCaprio would do next. It’s a good thing viewers liked him, because in the following year, his stardom would be inescapable.

To say that Titanic kicked ass at the box office would be a gross understatement. The 1997 cinematic juggernaut smashed records that hadn’t even been set yet, and to this day remains the most successful film on DiCaprio’s resume. And is second only to Avatar when talking about the highest worldwide grosses of all time. There isn’t a fan out there who doesn’t have the lyrics to Celine Dion’s “My Heart Will Go On” memorized. As Jack, Leo is a third-class passenger who falls for a first-class lady named Rose. DiCaprio and co-star Kate Winslet are so perfect together, that even the happy moments their characters share are heartbreaking. Director James Cameron brought stunningly realistic visuals to the screen like the public had never experienced before. Playing Jack put Leonardo DiCaprio on a trajectory that ultimately made him the star he is today.

Like we’ve said before, if you want something done right, just hire Tom Hanks. The man can do no wrong. And DiCaprio was along for the ride as Frank Abagnale Jr. in 2002’s Catch Me If You Can. Based on the story of a real-life conman, the movie follows Leo’s character as his deceptions become increasingly sophisticated. With Hanks alongside as the man obsessed with taking him down, their cat and mouse dynamic is so engaging that you can’t help but root for them both. But just days earlier, audiences were watching the actor in a different movie.

Once in a blue moon, a powerful actor attracts a powerful director, and together they perform motion picture witchcraft. In 2002, Martin Scorsese tagged DiCaprio to play the protagonist in his movie Gangs of New York. Released five days before Catch Me If You Can, 2002 was shaping up to be a pretty good year for Leo. The famous director is known for having very specific criteria during the casting process for his films, so being hand-picked by him is kind of a big deal. Since the Scorsese train stops for nobody, the actor hopped aboard at his first opportunity. And as we’ll see, this collaboration marks the beginning of a beautiful big-screen friendship.

When Scorsese needed someone to play the eccentric Howard Hughes in 2004, he knocked on Leo’s door. Clocking in at nearly three hours, The Aviator won five of the eleven Oscars it was nominated for. And DiCaprio even took home a Golden Globe for Best Actor. The critics who were able to hold their bladders long enough to make it to the end praised the complexity of his performance. And those who used the movie’s runtime as an excuse not to see it must be forgetting that Titanic was almost a half hour longer, and we didn’t hear any complaining back then.