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Meet a Hamilton Star

From East Bay rapper to Broadway star, Daveed Diggs Shines in the Hit Musical Hamilton.


Chris Crisman Photography

Daveed Diggs’ voice is hoarse. Really hoarse. Like maybe we should postpone this interview hoarse.

To further fatigue the voice of Thomas Jefferson and the Marquis de Lafayette—the two characters Diggs plays in Hamilton, the hit Broadway musical about the nation’s first secretary of the treasury—would be a disservice to the evening’s sold-out performance. Diggs assures me that he’s taking the matinee off to rest. Still, for more than a year, the Oakland native never missed a show, and with eight performances a week that require him to deliver rap lyrics about the issues of the American Revolution—immigration, death, taxes, liberty, and of course, sex—such ailments are inevitable.

For Diggs, a Berkeley High grad who went on to pursue a theater degree at Brown University, rap has always been in the forefront. He recalls disembarking from the bus to Hebrew school—Diggs is the son of a Jewish mother and an African American father—to buy E-40 rap tapes on the street corner, and “spitting” rhymes with friends at Alameda Beach.

Later in life, he joined the New York City–based improvisational rap ensemble Freestyle Love Supreme along with Hamilton creator Lin-Manuel Miranda—a fortuitous friendship, to say the least.

Now 34, Diggs is an award-winning Broadway star who proudly inflects his roles with East Bay élan. A July 2015 review in The New York Times praised Diggs’ Thomas Jefferson, saying that the character “swaggers like The Time’s Morris Day, sings like Cab Calloway, and drawls like a Dirty South trap-rapper”—not too shabby for one of history’s most preeminent slave owners.

These kinds of artistic paradoxes—from the cast of minorities to the sheer audacity of a rap musical that fits in more than twice the words per minute of any other Broadway production—are the reasons Hamilton is expected to sweep the Tony Awards on June 12, before kicking off its national tour in San Francisco next March. Here, Diggs discusses big breaks, the speed of his in-character rhymes, and how to spot the coolest cat in the room.


by Joan Marcus

Q: You play two different characters. How do you make them different?

A: They are fundamentally different people. Lafayette is so young when we meet him, and he’s left everything to come fight the revolution. He’s incredibly idealistic and all heart. Jefferson is much more of a vicious character. He’s the older out-of-touch guy, even though he’s my age right now. He’s so privileged and has always been in a power position. Where Lafayette is always building things up, Jefferson is trying to tear them down. The fourth wall [the imaginary barrier between the actors and the audience] is really in play for Lafayette, but Jefferson is such a hound for attention: The first thing I do when I’m playing him is look out into the audience and wave and blow kisses. Lafayette stands a lot taller, straighter. Jefferson walks with a lot of confidence. I literally stole his walk from my grandfather.


Q: Based on Ron Chernow’s best-selling biography of Alexander Hamilton, the musical focuses on history, but the themes feel modern and fresh. What do you hope people take away from the story?

A: History is really about who’s telling the story. We’re used to learning about historical figures once they’ve been turned into statues or monuments. The thing about this show is that it turns those statues and monuments into real people who are flawed and passionate. The real takeaway is that history is about actual people. We can examine someone’s flaws and still appreciate his or her successes.


Q: Why do you think Hamilton connects so well with audiences—even the ones who haven’t seen the show and have only heard the cast recording?

A: It’s hard not to fall in love with these characters because you know we’re telling a true story. There’s somebody for everyone to root for, from [Hamilton’s wife] Eliza to Hercules Mulligan: Before this, who even knew who he was? He was a spy, pretending to be a tailor, making clothes for the British, and bringing back their secrets. But my entry point was the rapping—a purely musical interest. You probably hear a lot more complexity on the album than you would hear live. The production is so pristine.


by Joan Marcus

Q: Is the rapping in Hamilton in line with your personal rap style?

A: This stuff is slow for me. I’ve been a fast rapper all my life, and even though it’s very, very fast for a musical, the rapping is the easy part. Everything else is hard. I’m not a dancer, for example. Our choreographer, Andy [Blankenbuehler], surrounds me with the most incredible dancers in the world, who make me look a lot better than I am.


Q: What’s been the highlight of the ride so far?

A: Performing for the First Family at the White House. They’ve been so supportive of this show. You know, I’m really going to miss this president.


Q: Have you been thinking about life after Hamilton?

A: I think about it, yeah. I know it involves a lot of rap music.


Q: Are you still making your own music?

A: All the time. I’m in a really creative phase right now.


Q: How is it inspired by Hamilton?

A: I think the musical has inspired me to be a little more personal in my own writing. It’s made me want to put something out there that I can use as a history—music about things that I, Daveed Diggs, have lived through and personally believe in. There can be nothing else in the world like it.


Q: Hopefully, it brings you back to the Bay Area. Would you freestyle a little rap about Oakland?

A: It’s a little early in the day for that!


Q: Are either of your Hamilton characters Oaklandish?

A: I mean, I’m Oakland to the bone, so they must be on some level. I think there’s a lot of Oakland in Jefferson, actually. He reminds me of the people of my grandfather’s generation—real slick-talking, smooth, “never let them see you sweat” kind of men. The definition of swagger. In fact, the presentation of cool is a very Bay Area thing. If you’re in a room with one person from Oakland, that person is always going to be the coolest one there.


Q: You were a performer long before Hamilton. But would you say Hamilton has been your big break?

A: It’s totally changed my life. It’s given me access to artists and creators I never would have met before. But I’m not sure a “big break” exists because when you’re an artist, you just keep doing your thing and hope that it works out. At the end of the day, Hamilton is just a bunch of friends doing things they love together. This experience has sort of re-affirmed everything that I had hoped to be true about being a living, breathing, working artist: If you wholeheartedly pursue the things you love and believe in, things can actually work out. hamiltonbroadway.com.


East Bay to Broadway

Meet 5 local stars who made their way to Broadway as well!

Jason Hite // by Isaac James

Antioch native Jason Hite’s first taste of the theatrical glory came when he played the slick-talking slacker Kenickie in his high school production of Grease. Forays off-Broadway (most recently: Bare) and on the small screen (The Good Wife, Madam Secretary) ensued, and this year the 26-year-old is making his Broadway debut as Sean Bateman in the musical stage adaptation of Bret Easton Ellis’ American Psycho.

Alysha Umphress, an alum of the Lesher Center’s Young Rep program, delivers scene-stealing performances in such Broadway productions as On the Town and American Idiot (not to mention a role in the epically hilarious off-Broadway hit Silence! The Musical). This “brassy, sassy, dramatic mezzo,” as she’s been called, performed at the Diablo Regional Arts Association’s annual fundraising gala, On Broadway, last October.

Had his childhood obsession with baseball dictated his career, we may have never had the privilege of seeing Danville native Bryce Ryness turn on the cranky to play Miss Agatha Trunchbull, the dictatorial headmistress in the national tour of Matilda, the Musical. Before that, you may have spotted the married father of three in NBC’s Pan Pan Live! He is also one of the few people who knows what it’s like to sing back-up for The Who’s Roger Daltrey.

Courtesy of Alysha Umphress

A highly coveted phrase now describes Hayward native and fellow Freestyle Love Supreme rapper James Monroe Iglehart: Tony winner. He earned the Best Featured Actor award in 2014 for his role as the Genie in Aladdin. Needless to say, such impressive credentials are bound to open up a whole new world (sorry, we couldn’t resist). In March 2015, Iglehart starred in Tina Fey’s Netflix series Unbreakable Kimmy Schmidt as Coriolanus Burt, the bane of the Broadway hopeful Titus Andromedon’s existence.

Moraga’s Bryce Pinkham has played Monty Navarro, a low-on-the-totem-pole heir to a family fortune, in A Gentleman’s Guide to Love and Murder, which swiped the Tony Award for Best Musical in 2014. The Grammy- and Tony-nominated performer most recently starred as gay pediatrician Peter Patrone in the 2015 revival of Wendy Wasserman’s comedic exploration of feminism, The Heidi Chronicles.

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