Leonardo DiCaprio in 'Shutter Island'

He's 35 years of age but some people think he still looks like a baby-faced boy. Leonardo DiCaprio may look younger than his years, but he's come a very long way from playing a homeless kid on Growing Pains.

His striking good looks were complemented by a fierce intensity in This Boy's Life; he would need every ounce of courage to stand up to Robert DeNiro as his eventual stepfather, a hidden cauldron of anger and rage. DiCaprio faced up to another challenge in What's Eating Gilbert Grape, fleshing out the more demonstrative role as Johnny Depp's brain-damaged younger brother and earning an Academy Award nomination. Lesser actors would have been glad merely to have survived acting against a powerhouse like DeNiro or a young male icon like Depp; DiCaprio appeared to thrive under the pressure, moderating the showy nature of the roles with a welcome degree of subtlety. Either of those roles could have been his best, but he had more to offer.

His supporting bit in The Quick and the Dead, Sam Raimi's Sharon Stone-starring Western, alongside Russell Crowe and Gene Hackman, feels like a lark, something done purely for fun. He turned back toward darkness for his first lead performance in The Basketball Diaries, an edgy performance in an uneven film, and then an even less commercial role in Total Eclipse, convincingly essaying a massively troubled man in love with another troubled man. The latter two -- raw, roiling in tension -- are definite contenders for his best role ever.

Then came the one-two romantic punch of Romeo + Juliet and Titanic, with a little Marvin's Room drama thrown in for good measure. In the latter, he once again showed that he belonged on screen with the likes of Meryl Streep. His charm and charisma made it deceptively easy for him to put on the mantle of Young Romantic Lead, and millions swooned as his heart melted with Juliet and Rose. His acting in those parts is fine and capable and light on its feet, not easy qualities to maintain when you consider the strong personalities of the directors involved, but neither is his best role.

Leo now stood on top of the worldwide box office. Could he resist the siren call of the big bucks? The Man in the Iron Mask replied with a muffled "no." Danny Boyle's The Beach felt muddled. Woody Allen's Celebrity was awful and Leo looked confused. His personal life was getting more attention than his movies. Maybe his best work was behind him.

Don't tell that to Martin Scorsese or Steven Spielberg. Five years after the enormous success of Titanic threatened to derail a serious acting career, DiCaprio was back on track and better than ever. Gangs of New York and Catch Me If You Can were big-budget, commercial-minded projects, but they were also ambitious and daring. As I've written here in the past, DiCaprio was sometimes uncertain in Gangs and outshone by Daniel Day Lewis, but he was a deft, lithe, sincere liar in Catch Me, digging beneath the surface of a charming, counterfeit personality. Catch Me If You Can was his best work up to that point.

Since then, DiCaprio has worked with Scorsese three more times, a collaboration that continues to irk some people, as in: 'What does he see in him?' He made the workmanlike Blood Diamond, toed up as Action Jackson to an office-bound Russell Crowe in Body of Lies, and tried (and failed) to rekindle a doomed romance with Kate Winslet in Sam Mendes' disastrously miscalculated Revolutionary Road. None of those latter three represent his best work, so we circle back around to his films under the direction of the aging Scorsese.

DiCaprio strained mightily to bring Howard Hughes to life in The Aviator, but the seams were showing. He stood out in The Departed for his steely resolve and haunted determination. Yet it's his performance in Shutter Island that sets a new standard.

As a tough detective, DiCaprio is searching for something very important and extremely personal. He thinks he knows what he's looking for, but he doesn't, and that's part of the reason why his search becomes so tragic. My opinion of the film, and of his performance, has only risen since I first saw it. DiCaprio never resorts to tics or mannerisms to communicate the flaws of his character. He's a lost soul, doing the best he can, and visions of the film continue to haunt me, gnawing into my sleep.

Leonardo DiCaprio's best role is in Shutter Island.

[* UPDATE: Shutter Island is now available on DVD and Blu-ray. Check this week's Spin-ematical for more information.]