A Drink with Daveed Diggs

Daveed Diggs is drinking bourbon on the rocks—Woodford Reserve, to be exact—as we sit in a 1970s-chic booth at the popular East Los Angeles bar Blind Barber. The drink is one you might associate with a laid-back man’s man at ease and in the moment. And though the signifiers from a bygone era are fitting, they hardly sum up the person in front of me.

Diggs appears to be at home here but not because he subscribes to some rakish Rat Pack ideal. The 38-year-old Oakland native was raised to embrace a more complex sense of identity. That much is apparent when you meet him, with his omnipresent grin and abundant Afro of curls.

The performer, who came up in theater and landed Grammy and Tony awards for his work in the Broadway megahit Hamilton, is uniquely qualified to usher in a new future for depictions of masculinity. This May he’ll star in TNT’s Snowpiercer— a television adaptation of the 2013 sci-fi film from director Bong Joon Ho (whose latest movie, Parasite, made him the only person of color nominated for a 2020 best-director Oscar). Diggs co-wrote and starred in his own film—2018’s Blindspotting, earning him an Independent Spirit Award nomination for acting—but with the new gig he’s finally getting the opportunity to show his version of a mainstream leading man. For Diggs, this evolution comes with the responsibility to make good use of his growing platform.

“The value of black life has been displayed for us so much in the past few years, and it’s been pretty disheartening,” he says. “All the ways we thought we might have been valued turn out to be not true. And then we have people in power who are not disheartened by that and, in fact, are playing right into it. If you have an election coming up, it’s fucking stressful.”

His sense of innate human value likely came from his father, whom Diggs describes as having “never withheld a demonstration of love to anybody,” particularly not to him and his brother. Diggs told Esquire in 2016 that his dad “doesn’t necessarily identify as gay, but I’ve known my father’s boyfriends [throughout] my life.” As Diggs tells PLAYBOY, “We lived in dangerous places, but I never felt unsafe with my father around. Strength and emotion were not opposites. They were all in one man for me, and in one man without a heteronormative identity.”

Stemming from this, he’s adamant about remembering where he came from. “It’s an interesting thing to make art for a place that doesn’t exist,” Diggs says, speaking of an Oakland that’s nearly unrecognizable from the place where he grew up. “Oakland is changing so fast, and most of the people I grew up with live elsewhere. Even if they’re still in the Bay and still claim it, they live on the outskirts and come into Oakland to hang out sometimes.”

Set in his hometown, Blindspotting tackles themes of memory and loss—the latter due in this case to gentrification and displacement of natives. Although it’s set far, far away from Oakland, Snowpiercer grapples with similar themes: A failed global-warming experiment kills much of the planet, plunging it into ice and carving ever-deepening divisions between the haves and the have-nots.

The idea of using science fiction to confront real-world concerns has always interested Diggs, a self-proclaimed Star Trek fan. “Fucking climate change scares the shit out of me right now,” he says. “Snowpiercer barely seems like scifi at this point.”

If there’s another thread running through Diggs’s projects—which will soon include the Showtime limited series The Good Lord Bird, in which he plays Frederick Douglass—it’s that he wants to choose characters who continue to push our cultural conversation forward. (He’ll also put his spin on a beloved crustacean when he voices Sebastian in Disney’s remake of The Little Mermaid.) “I don’t like to play in worlds where stupidity is excused or justified or is part of the world,” Diggs says, emphasizing his preference for complex studies of human desires and conflicts.

That’s true even when they’re controversial. Take his recent turn in the off-Broadway play White Noise: In last year’s buzzy production from Pulitzer Prizewinning playwright Suzan-Lori Parks, his character has an encounter with the police and then asks his white friend to be his owner in order to feel safer in the world. It is dangerous territory for a play to explore, but Diggs loves working with black artists who have something to say about race and politics in America. Among those who earn his praise: Moonlight co-writer Tarell Alvin McCraney, poet Chinaka Hodge (“my favorite writer of words”), 2019 Pulitzer-winning playwright Jackie Sibblies Drury and Slave Play playwright (and Fall 2019 Playboy Interview subject) Jeremy O. Harris.

Diggs has learned a lot shooting Snowpiercer scenes alongside his Oscar-winning co-star Jennifer Connelly—lessons that will come in handy as he seeks to increase his impact outside of the New York theater scene that incubated his career.

“Music these days has become accessible to everybody, and that’s good, so I always want to keep making music,” he says. (In addition to his many acting projects, Diggs fronts the hip-hop group Clipping.) “That’s another reason it’s important to work in TV and film: Those are actually more accessible than theater in a lot of ways. Even if I’m sort of uncomfortable with them, I want to figure out ways to tell the important stories by those means.”

Talk of the future raises another question: Has his father’s evolved masculinity inspired Diggs to raise a family of his own? The artist says he “desperately” wants to have kids and explains how his creative choices will factor into the herculean task of fatherhood.

“Raising black kids in the world, I want them to be less afraid than I was,” he says. “I wonder, What the hell kind of place am I bringing a kid into, and is that okay? That’s stressful, and it also makes me want to keep making art that’s important and speaks to those things.”

He concludes the thought on a note that would surely make his father proud. “I want the world to be better for my children, whenever they get here.”