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Leonardo DiCaprio has been considered one of the big A-List stars for around twenty years now. He went from blue eyed teen heartthrob to serious actor who surprisingly has yet to win his own Oscar. His latest is the Baz Luhrmann movie interpretation of The Great Gatsby. DiCaprio has proven himself to be a fine actor who deserves all the praise he’s received over the years, but he hasn’t always made the right decision when it came to picking out his roles. So now we’re here to remind you of some of the best, and worst, movies that the star has been in. 

Top Five Best Leo DiCaprio Films

5. Shutter Island

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The crazy twists and turns that reside in this mystery thriller were plenty enough to keep some folks’ attention from start to finish, but unfortunately Shutter Island never got the kind of love that some expected. This Martin Scorsese film has been underrated as it’s an entertaining, visually alluring movie with an excellent cast. This tends to be the one DiCaprio film that some people may have forgotten about, but it’s still a fine and sad thriller to check out on a particularly rainy day.

4. Romeo + Juliet

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At the time Leonardo DiCaprio was best known for being the baby faced heartthrob that was gracing the covers of Tiger Beat. So when it came to casting the lead characters of Baz Luhrmann’s loud interpretation of Romeo + Juliet, Leonardo DiCaprio seemed to be the right choice. Luhrmann’s unique style of storytelling isn’t to everybody’s liking but his over-the-top visual nature worked fine intertwined with the work of William Shakespeare. Girls around the world swooned as they saw their favorite actor utter some of the most romantic dialogue ever written into a play. There have been a few interpretations done on this particular story but is definitely one that I may enjoy the most.

3. This Boy’s Life

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Whenever people bring up some of Leonardo DiCaprio’s early work, some folks fail to mention This Boy’s Life. The story centers on a mother and son who run away from one broken household to find themselves in an equally shaky one as she remarries another dangerously temperamental man. DiCaprio and Roberto De Niro are both the shining stars of this picture, particularly with their big onscreen interactions with each other as the stepfather and teenage son continually clash in the unstable household. It may not be a major blockbuster movie of the likes that we’re used to seeing DiCaprio in but it’s still a solid film.

2.  The Aviator

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One of the most powerful men in the world of aviation within the last century was Howard Hughes. He may have had one of the most colorful lives out there, which made for great material when it came time to adapt his life story into a movie. Martin Scorsese stepped into the director’s chair and brought Leonardo DiCaprio along to create The Aviator, which in my opinion is one of the better biopics to pop out within the 2000s. The spectacular cast, intriguing story and fantastic director made this movie one of the standout films of the Oscar season, wrangling up five Academy Awards.

1. Catch Me If You Can

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When Steven Spielberg made the 2002 film Catch Me If You Can, he created yet another crazy entertaining film that many of us, including myself, have been watching repeatedly ever since it’s release. Leonardo DiCaprio stars as Frank Abagnale, a teenager who manages to forge a number of checks in order to live the multiple fake lives he lead. It was a little hard to believe that this was based off a true story, but it is. DiCaprio gives one of the best performances of his career thus far and in my opinion the movie is a classic.

Top Five Worst Leo DiCaprio Films

5. Titanic

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Speaking of classics, Titanic is anything but that. The picture is a bore that combined a couple of the hot young actors of the time (Leonardo DiCaprio, Kate Winslet) and sandwiched them together with the over-the-top effects of James Cameron. Sure the love story is relatively sweet but it doesn’t do much of anything else. It serves no purpose other than to show how cool it looks when you properly have enough special effects to recreate the sinking of the Titanic. No thank you, I don’t really need to see that. My imagination is good enough and won’t cost me a movie ticket and a couple of hours worth of my time.

4. The Great Gatsby

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Sigh. The worst part about putting The Great Gatsby onto this section of the list is that Leonardo DiCaprio fit perfectly into the role of the mysterious Jay Gatsby, but his acting wasn’t enough to keep your attention. The latest movie adaptation of the famous F. Scott Fitzgerald novel comes off as a cinematic mess all done by the hand of Baz Luhrmann. Now don’t get me wrong, I have a soft spot for Moulin Rouge and Romeo + Juliet, but The Great Gatsby was just embarrassing to watch. At times Luhrmann held back, other times he was going off in full crazy stylistic force and it never balanced itself out like in his previous films.

3. Blood Diamond

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There are movies like Blood Diamond where the filmmakers are trying to convey a message, but instead of subtly getting it across they smother you with it until the credits roll. There’s nothing particularly impressive about this film which fails to reach the level of significance it very much strives to be. While most of the performances are solid, there’s not much else about this movie that’s particularly memorable, which explains why folks have lost interest in it over time.

2. The Beach

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Do you remember the movie The Beach? You probably don’t, and that’s for good reason. There’s nothing special about the Danny Boyle movie at all. It was one of those situations where they lumped together the hot director of the moment with the biggest teen heartthrob that was gracing the big screen. What resulted was a lackluster adventure thriller centered on a one dimensional American brat who decided to take a vacation only to end up in all sorts of danger. The Beach marks a brief low point in the actor and director’s careers, which is sad because individually they’re both rather spectacular.

1. J. Edgar

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Once upon a time some folks thought it’d be fantastic if they were to make a biopic on a disgusting individual who so happened to create the FBI. When they cast Leonardo DiCaprio to play the iconic FBI founder in J. Edgar, everybody thought that the Oscar would be in their hands that season. Boy were they wrong. J. Edgar comes off as a accidental comedy as DiCaprio delivers one of the worst performances of his career. The story was all over the place, the makeup was awful and the whole love story between J. Edgar Hoover and his right hand man was the funniest part of the movie. Everything about J. Edgar was awful and should never have been made.

The Great Gatsby is out in theaters now, in both 2D and 3D.

What’s your favorite DiCaprio? What’s your least favorite?