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.