Utkarsh Ambudkar performing with the improv-rap troupe Freestyle Love Supreme at the Booth Theater in New York, Sept. 21, 2019. Ambudkar has played memorable parts on television shows, starred as the romantic lead in the independent film “Brittany Runs a Marathon” and steadily released his own music. Image: Jeenah Moon/The New York Times
LOS ANGELES — In 2004, Utkarsh Ambudkar completed the acting program at New York University’s Tisch School of the Arts feeling disillusioned. He’d spent his days in class but his nights at clubs in the East Village, freestyling and battle rapping — in his mind, he was much more of a rapper than an actor. A life chasing down parts in an industry where talent mattered less than “the amount of roles for people that look like you” seemed grim, he said recently, over a gargantuan bowl of chili at a restaurant near his Los Angeles home.
Fortuitously, he was soon introduced to Freestyle Love Supreme, an improv-rap troupe started by Lin-Manuel Miranda with Thomas Kail and Anthony Veneziale.
“Pups from the same litter,” Ambudkar, 35, said of the group, which presented him with an almost too-good-to-be-true opportunity: “I get to rap as good as I can rap? I don’t have to dumb it down? And I get to be as funny as I am? And I don’t have to dumb that down? Or tough that up?”
Since 2005, Ambudkar has been a part of the FLS performing lineup, which has appeared at Joe’s Pub, TEDxBroadway and on the Pivot TV network, among many other places; he has a tattoo of the FLS logo on his ribs. And when the group’s key players began working on other projects, including “Hamilton,” Ambudkar was involved: He played Aaron Burr in an early workshop and some readings.
But during that early-to-mid 2010s stretch, Ambudkar was struggling with alcohol addiction, which made him too erratic and unreliable for the quickly moving train that turned into the biggest Broadway breakout of this decade, cementing rap’s place on theater’s most prestigious stage.
“What we didn’t know as friends was that he was struggling in the way he was,” Kail said. “The stakes were high, and I didn’t know why he wasn’t responding.”
Ambudkar said he wasn’t being professional. “It was ego; it was being a daily marijuana user; it was partying at night; it was being preoccupied, growing up as a brown person, feeling unattractive and seeking validation of the opposite sex to sort of fill a hole, my self-worth.”
“Hamilton” became “Hamilton,” and Ambudkar, in 2014, became sober.
His career has taken a different path. He’s played memorable parts on television shows including “White Famous,” “The Mindy Project” and “Brockmire”; starred as the romantic lead in the recent independent film “Brittany Runs a Marathon;” and steadily released his own music.
And now, finally, he’s made it to Broadway — as one of the featured players in the limited engagement of “Freestyle Love Supreme,” which opens Wednesday at the Booth Theater.
That it took this long is bittersweet. “The biggest failure in your life is everywhere, ubiquitous. It’s inescapable,” he said, explaining the stresses of watching the success of “Hamilton” from afar — including Leslie Odom Jr.’s Tony win for portraying Burr — as well as the low-grade annoyance of friends constantly asking if he could help get them tickets.
But he prefers the silver lining: “Dude, what a gift. You almost drank yourself to death, and now here is such a clear, painful, concise, deep wound for you to see the importance in staying sober.”
“FREESTYLE LOVE SUPREME” is essentially a series of improv comedy games performed via rapping, relying on skills Ambudkar has been honing since he was a teenager, when he would make up songs as his friend played guitar.
“It’s probably a little bit — ‘embarrassing’ is the wrong word — but it’s a little weird to admit that freestyle rap comedy is probably the thing that I’m best at,” he said.
But that skill set is rare and difficult to fake. Ambudkar has an easy charisma and a clear-eyed candor. He uses his body stealthily and brings his voice into sharp focus on a dime. Freestyling is about alertness, timing and wit — it can provoke anxiety for spectators when it’s not done well, but Ambudkar rarely falters. For him, rapping is much like talking.
“He’s a new version of the classic entertainer — he can rap and dance; he can act great and be funny,” said comic Hari Kondabolu, an old friend.
Ambudkar has been onstage since a wrist injury in high school derailed him from playing basketball. He grew up outside Baltimore, where his parents, both research biochemists at the National Institutes of Health, settled after emigrating from India in the 1980s.
He took to hip-hop early, soaking up A Tribe Called Quest and Snoop Doggy Dogg. And after white children called him a racist epithet, he was embraced by the black children in his neighborhood: “They’re, like, ‘Where you from?’ I’m, like, ‘India.’ They’re, like, ‘We don’t know where the [expletive] that is, but he just called you the N-word so you’re with us.’”
He also struggled with how to express his heritage. “I went through a phase in high school to make people like me, where I would call myself — because of the ‘Simpsons’ stuff — I would call myself, like, ‘Slurpee Boy,’” he said, referring to the animated series’s character Apu, who has been criticized as a mocking caricature. “I stereotyped myself.”
In college, where his occasional dorm-room freestyle partner was actor and musician Donald Glover, he made his passion for rap part of his studies. “Utkarsh was definitely one of the most experienced and had done the most amount of work already in terms of identifying himself within the performance elements of hip-hop culture,” recalled his hip-hop theater professor, Daniel Banks, who credited Ambudkar for providing part of the inspiration to create a course in live hip-hop performance for the theater studies program.
After graduation, however, apart from his work with Freestyle Love Supreme, Ambudkar was largely coasting. “It just sort of didn’t happen for me in the supernova way that I had assumed it would, based on how easily it had come to me,” he said.
His career had been moving in fits and starts — beatboxing and rapping in “Pitch Perfect,” playing Mindy Kaling’s younger brother on “The Mindy Project,” a stint in a pop-rap trio called the Beatards. (“It’s embarrassing that we chose that name. It does not age well.”) But sobriety gave him new purpose, and clarity, and his work blossomed.
On the Showtime comedy “White Famous,” he was the agent with pinball energy propelling Jay Pharoah’s up-and-coming comic. On the big screen in “Barbershop: The Next Cut,” he was a light-touch quick-wit barber, and in “Brittany Runs a Marathon,” he played a slacker turned romantic hero. On IFC’s “Brockmire,” he was Raj, a hypergenial sportscaster and a gleaming foil to Hank Azaria’s sleazy rendering of the title character.
Concern about how South Asian men are represented on screen and onstage is a central concern for Ambudkar. Despite being asked, he never considered changing his name to cater to unfamiliar audiences, or executives. “People learned Galifianakis,” he said, referring to actor Zach Galifianakis.
In the forthcoming Disney live-action remake of “Mulan,” Ambudkar plays Skatch, a new character who’s a “swashbuckling con man”: “I felt fun and cartoonish and handsome and caddish and dirty.” His character also has an Indian accent, which he worried may be “a dead end” in some professional circles: “When, like, Johnny Depp does a British accent, or Angelina Jolie does an accent, it’s acting,” he said. “But when I do an accent, it’s not.”
In part to avoid such problems, Ambudkar has been working on writing his own projects, including one roughly based on his story: missing out on your biggest opportunity and trying to recover from the pain.
“I don’t think he has a personal ceiling,” Kondabolu said. “It’s about how hard everyone else makes it for him, what kind of parts are written for him.”
At his first Broadway performance, a 10 p.m. preview show on a Sunday night, Ambudkar hilariously and impetuously played the central character in an audience-derived story from a woman who, as a child, was forced by her father to play on the all-boys basketball team he coached and then never touched the ball all season.
But his most natural moments came during a segment where each cast member delivered true stories inspired by the same word; on this night, the word was Champagne.
Initially Ambudkar looked a touch uneasy as his castmates shouted funny, triumphant tales. But on his feet were sneakers customized with his name and the dictum “Spit Truth.” So eventually he relented, delivering a long sermon about how he let his great opportunity slip away, but how sobriety saved and restored him. He ended his verse with a stunner: “I was a champion of pain/But now I toast with Martinelli’s instead of Champagne.”
It shushed the room. “It’s weird when I’m rapping under the guise of entertainment, but what I’m really doing is just unmasking and being really raw,” he said the next day. “I’ve been doing this 15 years, but in those moments I think, ‘I seek out new experiences, and I’m about to have one.’”
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