Daveed Diggs never auditioned for Hamilton. In fact, he fell into the career-making musical smash by accident. But you don’t get halfway to an EGOT in one year without the raw talent to back it up, and Diggs has plenty. The proof? His dazzling smile and halo of curls seem to be everywhere we look these days, from our TV screens to our playlists.
But back to that accident. In 2012, the Oakland native was cobbling together a living as a performer, touring with his experimental rap group, Clipping, and substitute teaching to pay the bills. “I was living at the poverty line at this point—maybe,” he recalls. But his luck took an unexpected turn when a clerical error placed Diggs and another teacher, Anthony Veneziale, in the same Marin County classroom. Turns out they were both freestyle rappers—and like good improvisers, they leaned into the mishap and taught the class together. Diggs gave him a ride home that day, and eventually Veneziale invited him to join his freestyle rap group. Also in the group: Lin-Manuel Miranda, Hamilton‘s eventual creator and star, as well as the show’s director, Thomas Kail. Unbeknownst to Diggs, Miranda’s Pulitzer-winning opus was already in the works — and the rest is modern Broadway legend.
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Kail asked Diggs to take part in a workshop of Hamilton in the summer of 2013, where he originated the dual roles of fast-rapping (like, 19-words-in-three-seconds fast) revolutionary Marquis de Lafayette and Alexander Hamilton’s swaggering political rival Thomas Jefferson. Following a wildly successful Off Broadway run, Hamilton opened on Broadway in August 2015 and snowballed into a pop culture phenomenon that won the cast a Grammy for Best Musical Theater Album, and Diggs a Tony for best featured actor in a musical.
Barely a year out from his Tony win, Diggs is an increasingly familiar face, thanks to two memorable recurring sitcom roles: one as Perry, the crush du jour for Kimmy (Ellie Kemper) on Netflix’s Unbreakable Kimmy Schmidt, and the other on ABC’s black-ish as Johan, the free-spirited brother of Rainbow (Tracee Ellis Ross).
In fact, black-ish creator Kenya Barris wrote the role for Diggs after being “blown away” by his performance on stage. Over lunch, Barris pitched Diggs the part of Johan without an audition. “He was just so grounded and so cool,” Barris says. “He takes what’s on the page and brings more to it than you thought was there.”
When production started, Barris quickly realized he wasn’t the only one under Diggs’ spell. “The first day we had our table read, everyone at the company was there,” Barris recalls. He couldn’t figure out why so many people had shown up. “Then I realized, ‘Oh, they’re here for Daveed.’ I’d never seen that before.”
Diggs has mixed feelings about his sudden rise. “Everyone wants to talk to you when you’re in Hamilton, which is nice, but the only thing they know is Hamilton,” he says. “That was the weird thing—to have been an artist your whole life and have nobody care, and then all of a sudden everybody cares.”
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Growing up in the Bay Area, Diggs says his family was poor but “very happy.” Though his Jewish mother and black father weren’t together, they shared the responsibility of raising Diggs and his younger brother easily. “They were both very fun parents, but my dad takes his fun very seriously,” he explains. “We would get chocolate chip cheesecake for breakfast and then go to school.” It was in the fourth grade that Diggs realized he could make his classmates laugh by acting out poems. “I was very shy,” he says. “[But] I remember feeling very powerful at that moment.”
He replicated that feeling throughout high school in slam poetry competitions. “I was a good performer, so I could win with pretty subpar writing,” he says. After graduating from Brown University in 2004 with a concentration in theater, he moved back in with his mom in Oakland while auditioning for plays, working on music, and teaching. “It seems like I was doing so much, but it was just grinding,” he says. “I didn’t have another skill set.” Even his mother knew that to be true. “I tried to apply for a job as a waiter, and my mom laughed at me,” Diggs says. “She was like, ‘You can’t do that.'”
All that grinding has paid off: He’ll appear on the big screen in Wonder later this fall alongside Julia Roberts, Owen Wilson, and Jacob Tremblay. He’ll also executive-produce The Mayor, ABC’s upcoming fall series about a struggling rapper who runs for office — and if that’s not enough, he’s set to star on TNT’s adaptation of Bong Joon-ho’s 2014 dystopian film, Snowpiercer. Oh, and he’s working on music in his spare time, too. “I’m just trying to do all the things,” he says with a laugh. “I like acting. I like rapping. And it turns out, I like producing!” But with his years of hustling not so far in his past, Diggs is realistic about Hollywood’s fickle attention span. “I know it’s rare and doesn’t always last very long, so I’m trying to soak it up while I can,” he says as he heads into rehearsal for a movie he’s not even allowed to talk about yet. “When it all comes crashing down and I’m couch surfing again, I’ll remember these times fondly.” We have a feeling he’s going to be okay.