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27. 'Don's Plum'
DiCaprio settled a $10 million dollar lawsuit to keep this movie from North American theaters — that's how proud he must be of his embarrassing performance. And although it can be found outside the United States, it's not worth the trouble.
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26. J. Edgar
Hidden behind old-man makeup and sporting an indefinable accent, DiCaprio clearly tried hard to win an Oscar as the cross-dressing head of the FBI. On paper, with Clint Eastwood behind the camera, Leo looked Academy Award-worthy. On screen, Leo is boring and bloated.
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25. Critters 3
It's Critters 3 — we really can't rank it much higher.
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24. The Beach
Until Martin Scorsese took DiCaprio under his direction, most of Leo's post-Titanic career proved a little aimless — much like the drifter Richard he plays in The Beach.
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23. Total Eclipse
As an actor, DiCaprio consistently makes interesting choices. And that's the nicest thing we can say about his role as poet Arthur Rimbaud — it's interesting.
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22. The Basketball Diaries
DiCaprio is mostly unwatchable as Jim Carroll, a basketball star who falls victim to heroin. Read the book instead.
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21. The Man in the Iron Mask
Leo does double duty as King Louis XIV and his twin brother Philipe. To tighten his grip on the throne, the cold-hearted Louis keeps the kinder Philipe jailed and behind a mask. Credit to Leo for trying, but if you're looking for someone playing two roles in one film, watch Lindsay Lohan?s The Parent Trap.
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20. The Quick and The Dead
Even though Leo is playing a character nicknamed ''The Kid,'' he seems way too young
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19. Body of Lies
DiCaprio is perfectly competent as CIA agent Roger Ferris opposite Russell Crowe in the Ridley Scott thriller. But he's not particularly memorable either.
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18. Blood Diamond
Yes, he was nominated for his third Academy Award for Diamond — yet this wasn't even his best role of 2006. (That honor goes to his work in The Departed.)
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17. Gangs of New York
Overshadowed by Daniel Day-Lewis, DiCaprio mostly disappears into the background of Scorsese's epic. Luckily for DiCaprio — and us — Scorsese didn't give up on the actor. The two went on to form a lasting director-star relationship.
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16. Revolutionary Road
When Leo reunited with Titanic leading lady Kate Winslet, sparks flew all over again. This time, though, the two characters were at odds, spewing vitriol at each other while their marriage crumbles. In the end, it left us hoping for a third Winslet and DiCaprio movie.
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15. Marvin's Room
Despite its schlocky sentimentality, Marvin's Room is full of great acting, including DiCaprio's turn as an institutionalized teen.
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14. Shutter Island
DiCaprio masters the duality of Teddy Daniels, a widowed federal marshall who isn't necessarily what he seems, even if he doesn't master the Boston accent. (See also: The Departed.)
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13. This Boy's Life
As Tobias Wolfe, DiCaprio goes toe-to-toe with Robert De Niro in This Boy's Life, proving that at just 19, the baby-faced kid was on a path to become one of Hollywood's greatest talents.
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12. What's Eating Gilbert Grape
Leo earned his first Oscar nomination for his sweet and sensitive portrayal of the developmentally disabled Arnie Grape.
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It's a small role, but DiCaprio shines as the spoiled movie star in Woody Allen's film about a novelist-turned-celebrity-journalist.
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10. The Great Gatsby
Free of makeup and crazy accents, DiCaprio is charming and desperate as Jay Gatsby. Through Leo, you can feel Gatsby's carefully constructed facade about to burst under the pressures of society.
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9. The Departed
It's one of the best Scorsese-DiCaprio pairings to date — and it finally earned the director a much-deserved Oscar. Leo flourishes as the undercover cop, matching acting wits with Jack Nicholson.
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8. William Shakespeare's Romeo & Juliet
A dazzling Romeo in Baz Luhrmann's reimagining of William Shakespeare's play, DiCaprio's brilliant portrayal of the tragic lover lights up the screen.
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7. The Revenant
Hugh Glass isn’t DiCaprio’s best role, but it’s his most undeniable — at least when it comes to Academy Awards. Playing the 1820s frontier legend who was mauled by a bear and left for dead by his colleagues, DiCaprio checked every Oscar box and invented some along the way. Played real-life person: check. Suffered for his art: check. Slept inside horse carcass and dined on bison liver: check. It’s easy to see the similarities between the actor and the character: both refuse to be denied.
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6. Django Unchained
Leo never looks like he is having as much fun as he does under Quentin Tarantino's tutelage. Playing the dastardly plantation owner Calvin Candie, DiCaprio makes the second half of the movie all his own with his electrifying monologues and terrifying presence.
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5. The Wolf of Wall Street
DiCaprio earned his fourth Oscar nomination for playing the larger-than-life Jordan Belfort in The Wolf of Wall Street. The award eluded the actor once more as it went to Matthew McConaughey for Dallas Buyers Club, but the Martin Scorsese film still opened to critical acclaim and made more than $392 million at the international box office.
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4. The Aviator
Howard Hughes — a wealthy businessman afflicted with OCD and obsessed with planes — was not exactly a sympathetic character. But Leo humanizes the larger-than-life figure in his second outing with Scorsese, ultimately garnering Leo another Oscar nomination.
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Try not to think about the twisting-plot, the heavy-handed score, or the ambiguous ending. Just enjoy Leo as Dom Cobb, a man trying to get back to his kids in America. The movie's commercial and critical success is due in part to DiCaprio's mesmerizing screen persona.
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Our hearts will go on and on with love for DiCaprio in Titanic, which catapulted him to superstardom. Under those good looks and Hollywood swagger, it's easy to forget his nuanced and charming Jack Dawson.
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1. Catch Me If You Can
Leo puts the artist in con artist in Catch Me If You Can, where he stars as Frank Abagnale Jr., a real life criminal who posed as a pilot, doctor, and lawyer in his schemes to cash fake checks — and woo many ladies. DiCaprio is delightfully persuasive, deceptive, flirtatious, and sometimes tragic — and we dare you to find a better role, if you can.