Leo's come a long way over the course of his career. http://bit.ly/1PnfiJT
  1. 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.
  2. 26.
    'J. Edgar'
    On paper, with Clint Eastwood behind the camera, Leo looked Academy Award-worthy. On screen, Leo is boring and bloated.
  3. 25.
    'Critters 3'
    It's 'Critters 3'—we really can't rank it much higher.
  4. 24.
    'The Beach'
    Most of Leo's post-'Titanic' career proved a little aimless—much like the drifter Richard he plays in 'The Beach'.
  5. 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.
  6. 22.
    'The Basketball Diaries'
    DiCaprio is mostly unwatchable as Jim Carroll, a basketball star who falls victim to heroin. Read the book instead.
  7. 21.
    'The Man in the Iron Mask'
    Leo does double duty as King Louis XIV and his twin brother Philipe. 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'.
  8. 20.
    'The Quick and The Dead'
    Even though Leo is playing a character nicknamed "The Kid," he seems way too young.
  9. 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.
  10. 18.
    'Blood Diamond'
    Yes, he was nominated for his third Academy Award for 'Diamond'—yet this wasn't even his best role of 2006.
  11. 17.
    'Gangs of New York'
    DiCaprio mostly disappears into the background of Scorsese's epic.
  12. 16.
    'Revolutionary Road'
    When Leo reunited with 'Titanic' leading lady Kate Winslet, sparks flew all over again.
  13. 15.
    'Marvin's Room'
    Despite its schlocky sentimentality, 'Marvin's Room' is full of great acting, including DiCaprio's turn as an institutionalized teen.
  14. 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.
  15. 13.
    'This Boy's Life'
    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.
  16. 12.
    'What's Eating Gilbert Grape'
    Leo earned his first Oscar nomination for his sweet and sensitive portrayal of the developmentally disabled Arnie Grape.
  17. 11.
    It's a small role, but DiCaprio shines as the spoiled movie star in Woody Allen's film about a novelist-turned-celebrity-journalist.
  18. 10.
    'The Great Gatsby'
    DiCaprio is charming and desperate as Jay Gatsby.
  19. 9.
    'The Departed'
    Leo flourishes as the undercover cop, matching acting wits with Jack Nicholson.
  20. 8.
    'William Shakespeare's Romeo & Juliet'
    DiCaprio's brilliant portrayal of the tragic lover lights up the screen.
  21. 7.
    'The Revenant'
    Played real-life person: check. Suffered for his art: check. Slept inside horse carcass and dined on bison liver: check.
  22. 6.
    'Django Unchained'
    Leo never looks like he is having as much fun as he does under Quentin Tarantino's tutelage.
  23. 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'.
  24. 4.
    'The Aviator'
    Leo humanizes the larger-than-life figure in his second outing with Scorsese.
  25. 3.
    The movie's commercial and critical success is due in part to DiCaprio's mesmerizing screen persona.
  26. 2.
    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.
  27. 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.