I watched an amazing fight yesterday between these kids across the street from my house." Daveed Diggs puts down his fork so he can use his hands to punctuate the beats of this story about the scuffle he saw in his neighborhood while walking Soccer, the dog he shares with his girlfriend. "I clearly got there right after round one. Kids were celebrating, pointing, and telling jokes about the other kid on the ground, who was like, 'You didn't even hit me! You ready for round two?'"

Diggs told me he was shy when I sat down to lunch with him and the poet Rafael Casal, his friend and long-time collaborator, but his knack for warm and engaging storytelling instantly turns him into an unavoidably dynamic presence. It's not hard to understand why he was nominated for a Tony Award for his performance as Marquis de Lafayette and Thomas Jefferson in the Broadway juggernaut Hamilton. The 34-year-old Diggs is just as compelling and energetic to watch as he is to listen to, even when describing a schoolyard fight.

"Both camps had a conference about it, and then they were like, 'OK, we're gonna do this, let's have a second round.' The fight was literally the worst sort of slap boxing." Diggs laughs. "The kid who lost round one was slapped in the face but clearly ready to keep going, but everyone else broke it up. It was so cool—everyone else was like 'No, you're done, you're done.' It was the most organized schoolyard fight I've ever seen."

Meredith Jenks

The former middle school teacher is used to being on a different side of playground politics. After graduating from Brown University, Diggs returned to his native Oakland, California, to teach poetry and acting classes, and he developed a popular rap curriculum for seventh-grade students in the Bay Area. "It was cool," he says. "I got to teach these rap classes in tandem with the curriculum that was happening anyway." Diggs saw the effects immediately.

"The awesome and equally tragic thing is that all of those kids are old enough to form complicated opinions about things, and nobody cares what they have to say," he says. "It was nice to give them a place to read something they had written and the audience—the rest of the class—wasn't allowed to leave."

Meredith Jenks

Diggs knows a thing or two about hoping to sustain an audience's attention. He graduated from Brown with a degree in theater, and his hip-hop group, Clipping, signed to Sub Pop before he gained national attention for helping to bring rap to Broadway. Even though he loved teaching, he gave up the job in 2012 when he started to get more opportunities as a performer. It was a sacrifice; Diggs only wanted to do the job if his whole head was in it, and he didn't want to disappoint the kids by being yet another burned-out teacher just there for the paycheck. Still, he sits up straighter and talks emphatically when describing his time as a teacher, and clearly loved being part of his student's lives.

"The reason you write something that is exciting and visceral is to force people to hear what you have to say, especially if you're in any kind of marginalized community where people don't want to listen," he says, flashing his infectious smile. "You have to come up with tricks to make them listen."

Meredith Jenks

Diggs has certainly applied some of those tricks to his own career. The prolific musician spent most of his 20s bouncing around jobs between Los Angeles and the Bay Area: teaching and performing with Clipping. When it came to acting, he was frequently disappointed by the specifications of the casting calls when it came to race and gender, which made the already frustrating process of going out for auditions a source of disillusionment. "On one of the last auditions I did for a commercial, there was a room full of people like me," he says. "To walk into a casting room full of people who look like you is a crazy thing. What is the thing that necessitates all of us having the exact same shade of skin and having the same hair? What about this deodorant commercial needs that? [It was] like the light-skinned, big-haired section of Costco. I don't even think I stayed for the audition."

Based on his experiences with Hollywood typecasting, he certainly never dreamed he would end up portraying a U.S. president on Broadway. Even though he's crucial to the DNA of his role in Hamilton—Diggs worked on the musical in its genesis, flying to New York to participate in early readings of the show—he wasn't at all confident that he would get the part once a full production was mounted. "I just assumed I was a placeholder," he says. "I loved doing it so much that I was just going to do it every time I could." It was a team effort to get him to the stage—his mom even helped him fight for the role. "I was talking to my mom the other day about buying tickets to see my girlfriend in Trinidad," he says. "She laughed and said, 'Remember when you could only fly when I had frequent flyer miles from my business trips on Southwest? And that was literally the only way you went anywhere?' The producers flew me out sometimes, but several of my trips to do workshops for Hamilton were on my own dime—or on my mom's frequent flyer miles." Diggs laughs, remembering his personal investment in Hamilton's earliest days. "There were times when they said, 'You really don't have to be at this one,'" he says, "and I was like, 'Damn if I'm gonna let you see someone else play this role!'"

Meredith Jenks

Once you see him on the stage, it's hard to imagine anyone else playing the dual role of Marquis de Lafayette and the stunningly flashy Thomas Jefferson. Diggs is incredible as both characters—the former a French expat coming to the aide of the American revolutionaries, brandishing his rapid-fire verses as his ammunition; the latter, a genteel Southern gentleman who acts as a philosophical foe to Lin-Manuel Miranda's Alexander Hamilton. The show is, of course, a smash hit and the hottest ticket on Broadway. It earned its principal cast and creative team a Grammy for Best Musical Theater Album earlier this year, and it's up for a record 16 Tony Awards—with Diggs himself nominated for Best Featured Actor in a Musical. It's not a stretch to claim that Diggs is a standout among an ensemble cast—even if six of his fellow actors are also nominated for Tonys this year.

"I was like, 'Damn if I'm gonna let you see someone else play this role!'"

Recently, he had a chance to see what that looked like when he saw his own understudy perform. "I saw the show without me in it, and it blew my mind," Diggs says of being in the audience as opposed to on stage. "It was so good! I'm excited to see other people's take on it."

Casal always knew Diggs would land the part. "Who the fuck else is going to do the fast rapping part?"

Meredith Jenks

Diggs' signature rap style might have been a surprise to the rest of the world—one can't not be impressed that he spits 19 words in three seconds during the song "Guns and Ships," setting a definite record for Broadway rapping—but it's an extension of his progression as an artist. "I was so excited after opening night," Casal says. "And Diggs just told me he wasn't doing anything differently from what we've been doing for years."

Oakland takes up prime real estate in Diggs' heart, and he credits the Bay Area for giving him the freedom to develop his artistic sensibilities. "There was something about that environment that was really conducive to being an artist," he says, thoughtfully. "The lifestyle in the Bay Area is tough to beat—it was relatively cheap, great food, lots of outdoor space and art space, and ways to be inspired at the time. It was a beacon to artists who had been frustrated somewhere else—you could get the things that you needed pretty easily. I think it's important that your work is in conversation with artists in your community. It's nice to come from a place where I actually had and have a community of artists who call each other on the phone and make something new."

He's worried that won't always be the case. "Neither of my parents live in Oakland anymore," he says. "They both got priced out. The tide is changing very quickly. I worry about the sustainability of a viable arts scene there, because it's getting really hard to get the things that you need now."

That might explain why he's slowly bringing his friends to New York in order to continue working with them. "He literally moved to New York because I wasn't responding to him," Diggs laughs as he gestures toward Casal. The two have an easy language together, punctuated by laughter and finishing each other's stories. It's not about keeping it real—Diggs is buoyed by his friendships, and the history they share is an integral part of who he is at his core.

"Remember that time we played a show in Sacramento, and then we got a call to help with a documentary for our friend's production company?" Diggs says to Casal. "Our drummer had no idea. We were doing a show, and then we got the call, and said we're going to Los Angeles right now." Casal, laughing, chimes in. "There's no time to drop you off!" Did they kind of kidnap their drummer? "Yeah!" Diggs says excitedly. "The photoshoot was at 9 a.m., and it was 2 a.m. when we got the call. We drove down, and then drove back the same night." To Casal, it was a no-brainer. "You do it for friends," he says. "If they ask for something, you go above and beyond."

"This is the dude I want to be—the most charismatic person in the room, always."

Despite the all-consuming role of playing two revolutionary historical figures in Hamilton, Diggs is still focusing on creating something new in his off hours. With Casal, he's developing a play that wrestles with the concept of masculinity. "Everybody's definition of masculinity develops in very specific ways," he says. "I've always wanted to be my father. He doesn't necessarily identify as gay, but I've known my father's boyfriends [throughout] my life, and he's my role model for maleness. This is the dude I want to be—the most charismatic person in the room, always."

Diggs is also deeply considering the unique pressures of masculinity. "It's a construct, but there's a ton of pressure at all times," he says. "Part of masculinity is this idea that you can protect somebody, this idea of keeping the people close to you safe. It gets very tricky." Even though he's been putting these messages in his music for years, they seem to be more accessible to his audience lately. "I don't know if it's the world changing, if my position in the world changing, or both."

As his professional world swiftly changes, Diggs holds his friends closer and pushes forward. "When people who know and believe in each other get together to make a thing they feel powerfully about, those are the best things," he says. "We end up loving those things. Those are the things that last."

Meredith Jenks

Look One (lead image): Suit by Hermes and T-Shirt by Dior; shoes by Common Projects.

Look Two: Suit and shoes by Burberry Prorsum; shirt by Hugo Boss.

Look Three: Sweater by Saint Laurent; jeans by ACNE; shoes by Tommy Hilfiger; belt and watch by Hermes.

Look Four: Jacket and shirt by Dsquared2; pants by Herbler; shoes by Tom Ford.

Look Five: Coat by Hardy Aimes; sweater by Gucci via Mr. Porter; jeans by Burberry; shirt by Dior; shoes by Church's.

Photographer: Meredith Jenks

Stylist: Christopher Kim

Groomer: Janice Kinjo

Special Thanks: The Westin New York at Times Square