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Leonardo DiCaprio: Half a boy and half a man

What’s made the legendary actor’s transition from teen heartthrob to leading man such a challenge? That boyish face

When David Mamet’s “Sexual Perversity in Chicago” was turned into “About Last Night,” one of the best new lines the film offered was directed at Rob Lowe’s leading man, lamenting over his inability to find the right woman: “You’re too good-looking. Girls go out with you and get nervous. … Best thing that could happen to you is an industrial accident.”

Which brings us to The Dilemma of Leonardo DiCaprio. While he’s not the most ubiquitous of Hollywood leading men, he’s given a handful of strong performances since his big-screen breakout in 1993’s “This Boy’s Life.” His swoonability factor with young women played a key role in the global success of 1998’s “Titanic,” still the highest-grossing film of all time, even with “The Dark Knight” getting within firing distance this summer. Martin Scorsese, one of the leading filmmakers of our age, picked DiCaprio to star in his three most recent movies.

But here’s the problem: Unless he’s shot, costumed and made up just so, the 33-year-old Leonardo DiCaprio still looks like he’s about 17 years old. And that automatically limits the number of parts any man, regardless of talent, could play convincingly.

Early in his career, obviously, this wasn’t an issue. A gifted actor from an early age, DiCaprio was just 19 when he received his first Oscar nomination for an extraordinary performance in “What’s Eating Gilbert Grape,” playing the hero’s mentally disabled brother. While this is exactly the sort of role that often features the kind of acting that “Tropic Thunder” skewered so brilliantly, DiCaprio played Arnie without an ounce of sentimentality or condescension. He inhabited the role in such a way where audiences could never see the strings; there was no undercurrent of “LOVE ME!” that others might have brought to it.

Throughout the rest of the 1990s, DiCaprio specialized in playing troubled young people, from tortured poets (Jim Carroll in “The Basketball Diaries,” Arthur Rimbaud in “Total Eclipse”) to juvenile delinquents (“Marvin’s Room,” where he more than held his ground opposite Meryl Streep and Diane Keaton) to idealistic drifters (“The Beach”). He even brought a very modern spin to one of literature’s greatest sullen teens in Baz Luhrmann’s histrionic, amped-up “Romeo + Juliet.”

And then, of course, there was “Titanic,” the movie that rocketed him from critical favorite to It Boy. DiCaprio shrewdly brought his physicality to play here, swirling around Kate Winslet as the very embodiment of the sleek, post–Industrial Revolution man while Billy Zane’s boorish mutton-eater harrumphed about, slapping Winslet and pooh-poohing Picasso.

DiCaprio’s beautiful, doomed Jack pinned the actor to young girls’ bedroom walls in all four corners of the globe, and while very few actors ever get to reach that dizzying pinnacle of the zeitgeist, even fewer emerge as performers who get taken seriously as they transition into adult roles.

Adult roles an awkward fitDiCaprio was apparently having no such problem getting the work, having begun his alliance with Scorsese, but their first two collaborations were awkward ones, particularly for DiCaprio.

“Gangs of New York” (2002) called attention to DiCaprio’s cherubic face and slight bearing by surrounding him with appropriately thuggish-looking secondary players. The love story with Cameron Diaz also left him somewhat stranded — the actress physically overpowered him on screen, with a bearing and performance that were aggressively 21st century. (To be fair, the tedious “Gangs” was cursed with a bloated self-importance that can’t be blamed at all on its cast.)

Next came “The Aviator” (2004), with DiCaprio stepping into the wingtips of legendary financier, daredevil, ladies’ man and all-around Hollywood hot shot Howard Hughes. In this case the mustache wore the actor and not the other way around. While the likes of Cate Blanchett, Kate Beckinsale and Alan Alda were rather vividly bringing the 1940s and ’50s to life, poor DiCaprio seemed distinctly out of place; it was as though, on the day before shooting, the real leading man dropped out and was replaced by the star of East Sagamore High’s annual “Life of Howard Hughes” pageant.

Not that DiCaprio wasn’t still doing interesting work in this era — “Catch Me If You Can” (2002), for director Steven Spielberg, offered DiCaprio one of his meatiest roles, one that allowed for a youthfulness in both charm and appearance. As an ingenious confidence man who gets caught up in his own schemes, DiCaprio was afforded the opportunity to be brash and vulnerable, fast-talking and brooding, cynical and longing for human connection. The actor’s innocent visage was part of the joke this time; who would believe that such a fresh-faced kid was taking you and your money for a ride?

Third time’s the charmHis third time with Scorsese proved to be the charm, as “The Departed” (2006) both cannily exploited DiCaprio’s baby face and made him appear convincingly adult. As a young policeman going deep under cover in the Boston mob, DiCaprio brought a new kind of gravitas to the film, whether staring down capo Jack Nicholson or romancing therapist Vera Farmiga.

And 2006 proved to be a watershed for DiCaprio, as it also gave us “Blood Diamond,” an overwrought examination of the African jewel trade that nonetheless featured a convincingly mature turn by the actor. Both “Blood Diamond” (for which he received an Oscar nomination) and “The Departed” seemed to promise an onscreen DiCaprio who wouldn’t get carded at a liquor store.

Again, it’s not that DiCaprio isn’t an enormously talented actor; he just looks young, and it makes it tricky for him to be convincing filling certain shoes. “Blood Diamond” and “The Departed” proved that it’s not impossible for him to carry a certain kind of on-screen maturity, but he’s got to pick his projects carefully.

It comes down to a performer’s understanding of his own physicality: James Gandolfini isn’t going to play Nureyev any sooner than Andy Samberg would try to be Tony Soprano. Some actors have the gift of transformation — Philip Seymour Hoffman is much taller than Truman Capote, while Russell Crowe could convincingly play either a gladiator or a shlubby tobacco executive — and others can will that transformation upon themselves. (Christian Bale. End of story.) For DiCaprio, however, it seems to be more about knowing both the power and the limitation of his instrument, and his work of recent years seems to reflect his growing self-awareness.

He’s not out of the woods, yet, however — director Ridley Scott woefully miscast DiCaprio in the leaden “Body of Lies.” We’re supposed to believe him as a veteran CIA agent whose dedication to his work has cost him his marriage, but he comes off too much like a raw recruit to make this character biography believable. DiCaprio’s Roger Ferris wears facial hair to blend in with the Arab world and his adventures lead to him getting many cuts and bruises on his face — the next best thing to an industrial accident, apparently — but neither of those elements make the actor fully inhabit the role.

There are high hopes for this Christmas’ “Revolutionary Road.” Reteaming with his “Titanic” paramour Kate Winslet, DiCaprio plays an unhappily married Madison Avenue ad exec in the mid-1950s. After two seasons of “Mad Men,” if we can believe the similarly youthful Vincent Kartheiser as an up-and-comer in the advertising world, it should be a snap for Leonardo DiCaprio.