OM BOY: Gomo in Milan, where he lives and records.

Although he had a strong suspicion that he wasn't going to stay in monk's robes, Gomo returned to Sere Je to gut out the last three years, earning the equivalent of his monastic B.A., because he wanted to finish what he had begun—or had been begun for him. Music, mostly hip-hop, was his lifeline, in the form of headphones and a portable CD player. "I would spend hours just listening to music until, like, five in the morning," he says. "I felt connected to it, like my best friend, the thing that understood me. My attendant would knock on the door and be like, 'Yo, rinpoche, go to bed now.'"

Three years ago, he handed over his robes and moved back to Pomaia. His main monastic teacher was understanding, and he says even his disappointed mother told him, "'As long you don't say the F-word in your song, I'm good.'" For the past year and a half he's been living in Milan, and with the exception of a brief romance with a Guatemalan exchange student, he's been pursuing his music career with monkish devotion, living on a stipend provided by Italian patrons.

Despite being anointed Best Male Singer at last year's Tibetan Music Awards on the strength of one online single ("Photograph"), Gomo can fairly be described as a small fish in a small pond. He is waiting, anxiously, for the music business to lift him from obscurity. In the Milan studio, he listens to playback after playback of "Let Me Down," in which he raps: "Can't choke, I'm feeling like the necktie/ Of the exec who tells you whether your best try/ Will be enough…Afraid of looking foolish, but I'm brave enough to do it/ If you ever doubted your dreams/ Just play this shit and loop it."

He writes tightly constructed, melodic tunes, part rapped, part sung, delivered in a light, sweet voice—think Chris Brown or Drake with a hefty dose of boy band. The Italian arm of Universal Records likes what it's heard, but he's still waiting for a record deal. So far, the elder lamas have remained silent about his career move. I ask Gomo what he imagines the Dalai Lama makes of it. "He's checking out my videos on YouTube—like, 'That's hot!'" Gomo jokes. Then, in the earnest vein that's never far below his hip-hop veneer: "I'd be honored if he knew something about me. I was thinking to actually go see him. Let's see what will happen with the music, and if things start to ripen, maybe I'll go explain it to him."

• • •

When your father is a New York Jew, your mother is an English aristocrat, and your name is Ashoka Mukpo, you spend a lot of time answering questions about your identity. "It's like within 20 seconds of meeting somebody, I've gotta put my whole life on the table," Ashoka, 31, says. "I usually just say, 'Oh, my parents were hippies.' If it's a more formal situation, I'll say, 'Oh, my stepfather was Tibetan.'" And if he's talking to someone who knows something about the story of Tibetan Buddhism coming to the West, he'll share the truth. "Then I say, 'My dad is Chögyam Trungpa,' and God only knows what kind of absurd conversation is going to follow."

Ashoka's mother, Diana, married Trungpa at 16, taking his Tibetan family name, Mukpo. She stood by him throughout the seventies as he built a hippied-out empire centered in Boulder, Colorado, and achieved wider cultural renown as a guru to Allen Ginsberg and Joni Mitchell. Unlike the Dalai Lama, who sticks to the Buddhist basics—minimizing suffering in life—Trungpa initiated his students into the Tantric side of the tradition: the effort to liberate the energies of everyday life to speed up the path to enlightenment. His community, eventually called Shambhala, was notorious for its booze-and-sex-fueled blowouts that were rationalized as Tantric exercises—transmuting the poison of alcohol or liberating oneself from the attachment of conventional romantic love. "I don't know, man," Ashoka says. "I think if it were this day and age and I rolled up and saw a bunch of white people and all the crazy shit that was going on, I might head for the hills."

By 1980 Trungpa had grown increasingly erratic, and Diana, while remaining devoted, took a lover, Mitchell Levy, Trungpa's personal physician. Trungpa's own sexual infidelity was never at issue—he had been shamelessly promiscuous since puberty. When Ashoka was born in 1981, all eyes in the delivery room were trained on his lily-white skin. Trungpa, true to his credo of "crazy wisdom," was unperturbed. "I was his son," Ashoka says. "It didn't matter that I wasn't his seed—I was his son."

IN THE NAME OF THE FATHER: Ashoka Mukpo (right) was born to an American Jewish father and an aristocratic British mother but was raised as the son of Chögyam Trungpa, the legendary Tibetan lama who preached enlightenment and practiced free love and alcoholic excess. Left: Trungpa with Ashoka's half-brother, Gesar, in the 1970s.

Ashoka was recognized as a tulku at 8 months old. The previous Karmapa called Trungpa to announce he'd had a dream that Ashoka was the ninth reincarnation of Khamnyon Rinpoche. "They called him 'the Mad Yogi of Kham,'" Ashoka says of his spiritual forebear. "He had a bit of a reputation as a wild man, which I don't think I'm living up to."

Ashoka, who lives in London with his girlfriend, is in New York City for a United Nations conference. Wearing a gray pinstripe suit instead of his usual jeans and T-shirt, he bears a passing resemblance to a young Jeremy Piven. He's smart and tightly wound, guided by a righteous idealism that led him to work for the nonprofit Human Rights Watch for three years after college and most recently to the London School of Economics, where he earned his master's in international development. In the fall he's off to join a nonprofit working on land rights in Liberia. "It's actually mellower than people think," he says.

After Trungpa's death in 1987 at the age of 48, from the alcoholism that accompanied his relentlessly swinging lifestyle, Levy and Diana married and moved Ashoka to Providence, where family life settled into a closer approximation of the American norm. But Ashoka always knew he'd been marked for a special destiny as a spiritual leader, which was exciting, like having a secret superpower, but which also made him feel like a freak. He recalls the time his parents suggested he take two Tibetan monks who were visiting from a monastery in India to basketball practice. "I told them, 'You guys don't get how incompatible this is with my self-conception right now,'" Ashoka says. "When you're 15, you can't say, 'Dude, I'm a reincarnated spiritual master from the hills of Tibet, and my father was this womanizing, drinking, Tibetan-crazy-wisdom genius' without people thinking you're weird as fuck. Now it's just a pain in the ass."

Ashoka's identity confusion took on a poignant edge during a family trip to Tibet when he was 22. "My title and role is really meaningful to people," he says. "I had old ladies and kids coming up to me and crying. Peasants with nothing offering their life savings. For God's sake, someone put a sick baby in front of my face and asked me to blow on it. I did. I'm not going to be the guy who says, 'This whole thing doesn't make sense for me, sorry!' Sometimes I do feel like it wasn't my decision to take this title on, but now I feel like someone put me in the position of abandoning it."

Ashoka is on his way to a celebration commemorating the 25th anniversary of Trungpa's death at the Shambhala Meditation Center in Manhattan's Chelsea neighborhood—one of some 165 centers that, along with dozens of still briskly selling books, maintain Trungpa's legacy. We arrive late to the burgundy-and-saffron-draped hall crowded with New Yorkers in their twenties and thirties. After an hour or so of sitting on the floor cushions, meditating and chanting, volunteers pass around plates of potluck dinner and cups of sake, Trungpa's favored drink.

Ashoka does his part, eating and drinking merrily. But venturing beyond these rituals to live and teach as a tulku lama won't happen in this lifetime. "For me, going too far down the rabbit hole of Tibetan culture doesn't make any sense," he says. Not that he's discerned any pressure from the Tibetan Buddhist establishment. "It's easy for them to write me off. I'm the white guy."