Hollywood Mavericks – The Leading Man Leonardo DiCaprio, 38

Meet the emancipated Leonardo DiCaprio, a single-name superstar who’s broken free of the shackles that constrain other A-listers: Don’t accept a supporting role? (Too late.) Never mess with a beloved classic? (Whoops.) Under no circumstances play a bad guy? (Does a virulently racist slave owner count?)

“I apologize if my voice is out—I’ve been screaming all day,” Leonardo DiCaprio says from the Long Island set of Martin Scorsese’s The Wolf of Wall Street. Taking a respite in his production office, he sounds sleepy, scratchy, and, quite frankly on this late-October afternoon, a little spent.

Gone are the days of the biennial, or at best annual, Leo movie. After assiduously turning selectivity into an art form, long exercising the power of saying no, he is tasting the freewheeling joy — and pain — of saying yes: DiCaprio has three big films hitting theaters within the next year, and he’s producing three to boot. He’s coming off a year straight of wrangling, meetings, and a whole lot of acting. “This has been an exceptional situation,” DiCaprio says. “Filming three movies back to back to back, I don’t think I’ve ever done that.”

Curiously, he gravitated toward a timely theme in all of them. “In a weird way,” he says, “I realize these movies are about three different periods in American history, but all have a central character trying to hold on to the privileged life they’ve been given, by any means necessary.” He says this either unaware or unconcerned that it could apply to a 38-year-old movie star who is taking risks like never before.

That’s the thing about the Tao of Leo: He’s managed to cast a long shadow over Hollywood for two full decades without ever bowing to convention — no big-budget franchises, no rom-coms, not even a true action movie. “I don’t know why I choose certain films,” he says. “I just gravitate toward them and I don’t question that.”

Perhaps the boldest move in DiCaprio’s 20-year career is playing antebellum plantation owner Calvin Candie in Django Unchained. DiCaprio was drawn to him from the moment he read Tarantino’s script. He calls Calvin “one of, if not the most, despicable, indulgent, radical characters I’ve ever read in my life.” Naturally, DiCaprio signed on right away, and he promptly presented Tarantino with a gift: an antiquarian book on phrenology, the racist pseudo-science used to rationalize slavery. From there, DiCaprio and Tarantino made some striking modifications. “Writer-directors tend to be very precious about their material and their words,” he says, “but Quentin’s whole process is getting input from the actors and adding levels to their characters.” Perhaps no character evolved as much as Calvin, the master of Candyland plantation. “A lot of the talks we had specifically about phrenology really took him to a completely different level.”

Adding philosophical underpinnings to Calvin’s racism helped unlock the character, informing his affection for his surrogate father, a house slave played by Samuel L. Jackson, and his leering need to possess — as chattel — Django’s wife, played by Kerry Washington. Tarantino drew on phrenology to fashion an epic, incendiary monologue on racial superiority. The moment DiCaprio finished delivering the speech, the entire cast gave him a spontaneous standing ovation.

“He creates shades and layers and probes and just goes deeper than anybody else ever desires to,” says Stacey Sher, one of the film’s producers. “The last day, when everyone was saying goodbye to him, Leo was like, ‘Yeah, I’m sure happy not to be that guy anymore—it feels good.’ You knew he just felt lighter.”

“Of course it’s all risky,” he says, as a production assistant calls into the office to tell him he’s needed for the next scene. “I mean, that’s the excitement of doing it, you know?”

[Catch Him If You Can: “My whole thing has been to develop material outside the studio system for myself, and this expanded to funding material I won’t necessarily star in. I don’t need to wear the producer hat while making movies, but I love to have that collaboration.”]