The Essentials: Leonardo DiCaprio’s 10 Best Performances

“Titanic” (1997)
Most people need more than two films to remain forever “certified fresh” as one of cinema’s grandest romantic leads. In 1997, DiCaprio stood at the furthest end of the bow of a little ship screaming, “I’m the king of the world!!” Beyond the silver screen, that roughly translated to: “I’m not most people!!” After stepping out of the shoes of Shakespeare’s eternal star-crossed lover, he took quick reprieve from romance with a dark, supporting turn in “Marvin’s Room,” but when he finally agreed to be a part of James Cameron‘s ambitious epic romance —the most expensive film ever made up until that point— DiCaprio’s career would never be the same again. He portrays Jack Dawson, an impoverished Wisconsin rascal who wins a trip on the ill-fated voyage and, of course, falls in love with Rose DeWitt (Kate Winslet, in one of her essential performances). “Titanic’s” colossal success on every level drowns out all the components that worked together to make up the 2.1 billion dollar sum, but DiCaprio’s and Winslet’s onscreen chemistry combined doe-eyed star-making qualities with unfiltered talent for movie magic. After this film, the teen girl demographic experienced an unprecedented tectonic shift towards full-fledged Leo Mania. The combination of melodrama, romance, and tragedy in the screenplay sparkles through every pore of DiCaprio’s performance, carving the actor’s mainstream appeal in stone and giving him a one-way ticket to superstardom. Today, DiCaprio looks back at the mega event with lots of pride, and underlines how “the movie has really made me be in control of my career.”

“Catch Me If You Can” (2002)
Released a mere five days apart, Martin Scorsese‘s “Gangs of New York” and Steven Spielberg‘s “Catch Me If You Can” were both headlined by DiCaprio in what turned out to be another pivotal year in the actor’s career. It marked the first of five (and counting) films DiCaprio would make with Scorsese, but interestingly enough, it was his performance as real life conman Frank Abagnale Jr. in Spielberg’s film that turned more heads. It’s one of the director’s greatest films of the post-2000s period; combining the forces of comedy, family drama, adventure, and lots of chasing through Jeff Nicholson‘s deft screenplay with incredible economy. This balance of tone and swiftness of pace is reflected in DiCaprio’s central performance as a whip-smart teenager who rebels against his parents’ divorce by high-tailing it away through confidence scams; forging checks, impersonating pilots and doctors, and toying with Tom Hanks‘ FBI agent Carl Hanratty along the way. DiCaprio’s baby-faced features came in handy as the 27-year-old was seamlessly molded into a teenager, but even more crucial was his movie star charm working at maximum capacity for a role that actually required it. He turns suave into sensitive on a dime as Abagnale, making the forbidden fruits of a lavish lifestyle taste way sweeter than anything we’ve seen with the likes of James Bond. And working under the auspices of Spielberg was effective, because DiCaprio acts opposite Christopher Walken, Amy Adams, and Hanks with uncanny candor. This particular role also eerily anticipates his similar —albeit much more unhinged and darkly comic— turn as Jordan Belfort a decade later.

“The Aviator” (2004)
Before Jordan Belfort, though, DiCaprio would portray a drastically different but no less fascinating type of historical persona for Martin Scorsese. For their sophomore collaboration, Scorsese and DiCaprio brought the iconic life of Howard Hughes back onto the big screen and into public consciousness with “The Aviator.” For transporting us back into the Golden Age of Hollywood as if it was filmed in the 1930s, for that heart-stopping plane crash sequence that breathtakingly reminds us it’s a product of the 2000s, and for Cate Blanchett‘s scarily authentic Oscar-winning turn as Katherine Hepburn, the film is a fond memory. But revisiting it now leaves room for one particularly bitter aftertaste; it’s likely the origin point of DiCaprio’s now-infamously contentious relationship with the Academy. How on earth did he not win for this gargantuan performance? Looking back at the eventual Best Actor winner of the 77th Academy Awards, Jamie Foxx for “Ray,” doesn’t make the feeling any less caustic. DiCaprio’s portrayal of the eccentric-billionaire-turned-OCD-hermit was truly the first opportunity for the actor to completely shed his boyish persona and sink his teeth into a complex, multi-layered, larger-than-life biographical figure. He does so with infinite degrees of aplomb and astuteness. Ever the researcher, DiCaprio spent days in conversation with OCD experts and observance of those afflicted with the condition in order get inside the mental process of a germaphobe and hypochondriac. Watch the hand-rinsing scene, the “come in with the milk” and “the way of the future” scenes and tell me he doesn’t absolutely nail it; he powerfully tears your heart out portraying a man whose oversized ego didn’t exactly make him likable. Quite the opposite.