<p>“I remember going to my agents and saying, ‘I don’t want to do ['Hamilton'] anymore, but I am nervous I’ll never make any money again. What do you guys think? And they go, ‘Please leave the show,’ ” recalls Daveed Diggs, photographed with his labradoodle Moose on Jan. 13 in Los Angeles.</p>

“I remember going to my agents and saying, ‘I don’t want to do ['Hamilton'] anymore, but I am nervous I’ll never make any money again. What do you guys think? And they go, ‘Please leave the show,’ ” recalls Daveed Diggs, photographed with his labradoodle Moose on Jan. 13 in Los Angeles.
Photographed By Shayan Asgharnia

Daveed Diggs on Keeping It "Weird": I Can't "Become Somebody Else — I'm Just Not Very Good at That"

Before his string of mainstream success — 'Hamilton,' 'Snowpiercer,' that Hanukkah song about puppies — the actor, writer and rapper was perfectly content making genre-bending art that "no one liked" (until we all caught up, that is).

In the spring of 2017, the star of Broadway's Hamilton was hovered over a podium at Brown, his alma mater, ruminating on his own celebrity.

"Daveed Diggs was born on Jan. 20, 2015, four days before his 33rd birthday, at approximately 9:40 p.m.," he began. "He strutted down a fake staircase at The Public Theater in New York, singing a song his friend had written for him to sing, playing a man who would've beat him savagely for singing it had he been born in similar circumstances roughly 224 years prior."

Diggs may have written the contents of his speech tipsy at an airport bar the day or two before, but his decision to refer to himself in the third person was well thought out. As he told the expectant crowd of college graduates, he was still getting comfortable with the disassociation between the real him and the Daveed Diggs who seemed to emerge fully formed in the public consciousness with that breakout performance. Sure, the two shared a name, a face and, where it served the brand, a résumé, but that other Diggs, the one who won both a Tony and a Grammy for originating the roles of Marquis de Lafayette and Thomas Jefferson in the widely celebrated musical, arrived with a made-for-Hollywood story that didn't always line up with the more textured reality.

"It's an odd thing to navigate," he says now, acknowledging that popular culture has never been particularly good at embracing nuance in its celebrity narratives. "It becomes, 'Oh, he grew up poor and overcame that,' like 'That's a thing we can latch on to,' or he's Black or he's mixed or he's any of these things that were historically disenfranchised, and there's always a before and an after. Like a 'Hamilton happened and all of these things were fixed,' and the issue with that is it assumes that there was a problem before, and I'm not sure there was."

The real Diggs will tell you he grew up "poor and happy," shuttling between the homes of his white, social worker mother and Black, bus driver father, never wanting for a thing — that he spent more than a decade as a performer who happily plugged away at the margins until Hamilton declared him something more. "I know if you look at my history, it seems like I was a struggling artist. And I was, but I also chose those projects," he says of the kind of experimental art he never actually abandoned. "I didn't accidentally end up in Word Becomes Flesh or whatever it was, I chose to do that choreopoem and I liked living like that."

The question Diggs has been asking himself a lot lately is how much it all matters: Does he really need the public perception of him to line up with his own self-image, and, moreover, does he even want it to?

Whatever disconnect exists has hardly gotten in his way, after all. In fact, since May, the Oakland, California, native — who's just turned either 39 or 6, depending on your preferred Diggs timeline — has put out a first and, earlier this week, second season of TNT's dystopian thriller Snowpiercer, the Showtime miniseries The Good Lord Bird, the Apple cartoon Central Park, a film version of Hamilton, the Pixar movie Soul and a rash of new music, including both a Black Lives Matter protest anthem and a Hanukkah rap about puppies. And that's just the stuff that fits neatly in the narrative.

***

"I really don't have very many sad memories from my childhood," he says the first time we speak. Diggs is piping in virtually from the Los Angeles home he shares with his partner, Umbrella Academy actress Emmy Raver-Lampman, and a couple of dogs he's trying valiantly to keep out of frame. "What I remember is laughing so much my face hurt, and never ever being bored."

One of his more defining memories of his parents, with whom he's still fiercely close, dates back to preschool. The kids in his class were supposed to put on a performance for their families, but young Diggs preferred to do a gymnastics routine with his father. So, his mother worked it out with his teachers, and his dad turned up in matching rainbow tights. Reflecting on the day as he accepted his Tony Award many years later, Diggs thanked them both: his mom for giving him "permission to do something everybody else wasn't doing" and his dad for "supporting [him] and making it possible."

Though Diggs would find his calling in plays and poetry slams, it was his ability to clear hurdles, literal hurdles, at record speed that landed him his scholarship to Brown, where he became acutely aware of his Blackness for the first time in his life. Back in the Bay, he says, everybody seemed to be "a mix of something." He wasn't even the only kid in his circle who was half-Black and half-Jewish. Sure, there were the occasional moments where his particular mix would come up in conversation, but Diggs doesn't ever remember it being something he had to navigate. "Like, one time at the [Jewish Community Center], on Purim or some shit, a kid asked me if I would rather be white than Black," he says. "And I remember I said no and that was it. It didn't feel formative for me."

Then he arrived at Brown, which he'd been told was some sort of liberal mecca. The culture shock set in immediately. During a tour of the Rhode Island campus, he was greeted with a perplexing mix of waves, handshakes and hellos from every Black person who passed by. "It really weirded me out because it's not a thing that happened where I was from, these people who don't know me at all, and so I was very suspicious of it," he says. But a few semesters in, Diggs found himself doing the same thing, except now the greetings made sense to him. "We were such a stark minority there that you develop this muscle to be welcoming to anyone you see — an acknowledgment that we are both in this space that maybe isn't for us in a lot of ways. But, you know …" he pauses, shrugging, "you find your place."

For Diggs, that place was onstage. He threw himself into productions and workshops, graduating with a degree in theater arts before making his way back home. For years after, he shuttled between auditions and recording sessions, putting on concerts and plays. Whenever money ran low, which was often, he'd line up gigs teaching English or poetry, at one point even creating a rap curriculum for Bay Area middle schools. Ultimately, it was through a substitute teaching assignment that Diggs found his way to the improv hip-hop crew Freestyle Love Supreme, in which he met Lin-Manuel Miranda. Impressed by Diggs' talents — "he's a brilliant rapper and a brilliant actor," he says — Miranda invited Diggs to be part of the early Hamilton workshops that he was putting together. Diggs would play Alexander Hamilton's friend Lafayette in the show's first act, and Jefferson in the second. "Part of the development of [his character's] arc," says Miranda, "is me just writing the wildest shit possible for Daveed, and knowing that he can deliver it without breaking a sweat."

Once Diggs had gotten past his initial skepticism — "I thought it was a terrible idea," he reveals now — he loved being part of it: the material, the challenge, the sense of community. The more he did, the more he wanted to do. "I was gunning for [a role in the stage production] in ways that felt out of character," says Diggs. He kept in close touch with the show's director, Thomas Kail, who knew Diggs would be flying out on his own dime. "Tommy was really good about saying, 'Look, this workshop doesn't matter, if you happen to be here and you're available, of course we'd love to have you, but we're not showing it to anybody and it doesn't matter in the grand scheme of things, so don't worry about it.' But I didn't miss a single one. I just wanted to be around it and I was so sure that if they ever saw anybody else do it, they wouldn't ask me to come back."

Hamilton made its debut at The Public Theater on Jan. 20, 2015, and on Broadway soon after. Diggs was at virtually every performance until his last, 18 months later, on July 15 of the following year.

***

As the cast readied for Broadway, Diggs signed with a Hollywood manager, who took over his nightly allotment of tickets. She'd be trading them for favors, she told him: Anyone who was going to see Hamilton on one of Diggs' tickets would need to meet with him, too. "I thought it sounded like the ravings of a lunatic. Like, it's a play," says Diggs. "But her black-market ticket exchange is how I met Tina Fey and Kenya Barris and all these people who'd eventually give me jobs. And it was because she'd set these meetings for after the show, and people were so intoxicated by it. It was the craziest thing I'd ever seen."

Soon, Diggs had found his next act — or acts, as it were. He landed arcs on Fey's Unbreakable Kimmy Schmidt and Barris' Black-ish, and a greenlight for the Blindspotting screenplay that he and his childhood friend Rafael Casal had written a decade before but couldn't get off the ground. There was a flurry of film offers and endorsement deals, and even his experimental rap band Clipping, which, he says, "no one liked," got a bump.

"People were so overwhelmed by how fucking good Daveed was that they couldn't actually process how it happened without them knowing it," says Casal, who was there on Hamilton's opening night. "Because he wasn't just a rapper having a moment as an actor, and they could see that. And the shock that they weren't up on him made people swarm him." It was gratifying if a little confusing for Casal, who for years would watch as his best friend struggled to get traction, particularly as a rapper. They'd both send their music videos to local blogs and radio stations, and only Casal's, which was commercial in ways Diggs' wouldn't dare be, got picked up.

"People really didn't understand Daveed, and there was no big authority saying, 'This is it, guys.' No Kanye West being like, 'This is what music is now,' " his friend continues. "And it's interesting because we were doing this thing that's really popular now. Essentially Daveed was doing what Donald Glover was doing, five years before him, but Daveed didn't have Community. So, people would just go, 'Nah,' over and over and over again."

It didn't faze Diggs. He was never interested in courting mainstream acceptance, his collaborators say, always perfectly comfortable being "a little bit of the weirdo." In fact, even now, he insists he doesn't actually know how to make accessible art by himself. "Like, people saw an accessible value to the things that I can do," he says, "but that, for the most part, comes when other people put me in their things." Left to his own devices, Diggs says he'd be OK never doing Broadway again, content instead to fill his résumé with riskier plays on smaller stages, as he did in 2019 with White Noise. And anyone who thought he might ditch his avant-garde rap group once Hamilton hit doesn't fundamentally understand what makes Diggs tick as an artist.

"I remember all these people saying, 'Oh well, there goes your rapper. Guess the band's over.' But I never had any doubt," says Clipping's William Hutson, who's been tight with Diggs since grade school. "I was like, 'OK, Daveed got to rap on Broadway in a show called Hamilton, he didn't write one word of that show — and a rapper is not a guy who says words, it's a guy who writes words, and this is where he does that. Look, he's a great actor, but Daveed's someone who needs to be creative and he's not going to be satisfied just being on Snowpiercer or saying words out of cartoon mouths."

What Hutson didn't yet know is that at Diggs' first meeting with his manager, he handed her a copy of the latest Clipping album and asked that she listen to it before they discussed his career prospects. "I told her, 'You've only seen this other side of me, and this is actually the shit I'm going to keep doing and you have to be OK with that, too,' " says Diggs. "And then I said, 'I want you to tell me how I'm going to make money, but I want you to tell me how I'm going to make money and not how somebody else is going to make money because then I have to become somebody else and I'm just not very good at that.' " Nor, it was clear, was he interested.

***

When Diggs and I connect again a few weeks later, he's exhausted. Daveed Diggs, the celebrity, has never been more in demand, but the real guy is at a point now where he'd slow down if he could. Instead, he's playing catch-up on all the things he agreed to in that post-Hamilton period when everything was new and exciting and how could he not say yes? And, for the most part, he's pleased with the choices he's made. "I wanted to have all of these experiences," he tells me, "but now I've had a lot of them and I'm beginning to understand — and this is a COVID-ism — the actual cost of doing these things."

His partner had been gone for the past three months, working on a film in Australia, where he couldn't visit even if he wanted to. She was back for a few days, and then gone again; and soon he's off, too, back to Vancouver, where he'll be making a third season of Snowpiercer. So, he's trying to be more aware of the cost of what he says yes to, because the payment doesn't always make up for it, especially now that he doesn't have the same financial burdens. The other thing about having choice, he's learning, is that his choices now mean something. (For the record, he would have passed on the "Puppy for Hanukkah" opportunity, had it not been for his Clipping bandmates, says Hutson: "Jonathan [Snipes] and I were like, 'We could use the money. We're not touring this year, our band is sitting at home, so let's do some dumb sellout shit.' ")

The decision to play Sebastian the Crab in Disney's live remake of The Little Mermaid felt considerably more fraught. But after agonizing over it, Diggs signed on, joining a star-studded cast that includes Halle Bailey (as Ariel), Melissa McCarthy (Ursula) and Javier Bardem (King Triton). Miranda's on board, too, writing new lyrics for the film, which Disney has every intention of making a gargantuan hit. But even now, having "worked harder on this voice gig for an animated crab than almost any other role," immersing himself in research trips and dialect lessons, Diggs is still uneasy with his involvement.

"I was never gunning to be in these Disney remakes and, if I'm being honest, Sebastian comes with a lot of responsibility. For a lot of folks my age who are from the Caribbean, Sebastian was the first time they'd really seen themselves in American film, and I'm not Caribbean, so …" he pauses there, acknowledging that his team will probably scream at him for even talking about this, and then continues: "We'll see if people crucify me for it."

Diggs has never been blasé about the power of representation. He got to yes on The Little Mermaid in large part because of the bold casting of Bailey, a young Black star, as Ariel. He worked with Disney's Pixar, too, as one of its "cultural consultants" on Soul, the studio's first film with a Black protagonist, to make sure it was reflective. And now he's busy fighting his own battle on Snowpiercer. The show, like the Bong Joon Ho film, is a meditation on class, but once Diggs was cast in the lead role, he felt strongly that it should be one on race, too. As he reflected on the already aired first season, he recognized how little it had been. "Nobody was planning to make a show that was touching on race because they weren't necessarily planning to have a Black protagonist. But then they got stuck with me," he jokes, though he's quite serious about the matter. "So even though I know it wasn't, some things feel like a deliberate ignorance of race and that's not useful because I'm still onscreen. You can't not deal with it."

He has every intention of dealing with it on the TV reboot of Blindspotting, which he and Casal are writing now for Starz. The film, which premiered to raves in 2018, had been a decade or so in the making and, he's said, was heavily influenced by the 2009 death of Oscar Grant, who was fatally shot by police in a train station a few blocks from Diggs' former Oakland home. In addition to writing and producing, Diggs starred as a formerly incarcerated man who's trying to get through the final days of his parole when he witnesses the police killing of a young Black man. Diggs won't have an onscreen presence in the TV iteration, but has every intention of exploring the same timely themes.

"We said all the time when we were doing press [for the movie] that we wished it was a period piece," says Diggs, who found himself spiraling last spring, as yet another unarmed Black man was killed at the hands of police. He wrote a lot of "really angry music" during that time, he says, much of it in response to the expectation that he say something about George Floyd's death. Media outlets were eager for his thoughts and his fans and friends wanted to hear that he was OK. He wasn't, and he didn't have anything new to say. "I was like, 'See my whole career, see everything I've ever made, nothing has changed in the light of this particular Black death.' "

Three weeks later, on Juneteenth, he put out the song "Chapter 319" with Clipping. One particularly fiery lyric — "Donald Trump is a white supremacist, full stop/If you vote for him again, you're a white supremacist, full stop" — helped to give the band its first viral hit. By fall, the trio had released its fourth album, a strikingly timely if still niche horror-rap offering titled "Visions of Bodies Being Burned." Simply getting his messy emotions down on paper was cathartic for Diggs, as he suspected it would be. Music has always had a way of transcending him; it's one of the reasons he'd give up everything else in his career to keep making it, even if it doesn't feed the persona of that other Daveed Diggs, the one born six years ago.

This story first appeared in the Jan. 27 issue of The Hollywood Reporter magazine. Click here to subscribe.