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The Bravery of Being Yourself: Daveed Diggs on “Wonder” and “The Mayor”

“When I was in preschool, we were supposed to do a performance for the parents, and I didn’t want to do it,” said Daveed Diggs during his acceptance speech upon winning the 2016 Tony Award for Best Featured Actor in a Musical. “My mom talked to the teacher, she came back and said, ‘You don’t have to do [the performance], but you have to do something.’ I said, ‘I want to do a gymnastics routine with my dad.’ A couple days later, my dad showed up with me in matching rainbow tights and we did this gymnastics routine in front of the parents at the preschool. The important thing about that story is that my mom gave me permission to do something that everyone else wasn’t doing, and my dad supported me and made it possible.”

Thank goodness Diggs’ parents empowered his individuality as a child. His tireless charisma and tour de force musical abilities have made him one of the brightest modern talents on stage and screen. He earned a Tony and a Grammy for his dual performance as Thomas Jefferson and the Marquis de Lafayette in the original cast of Lin-Manuel Miranda’s Broadway sensation, “Hamilton.” Since then, he’s landed scene-stealing roles on TV shows such as “Black-ish” and “The Get Down,” while serving as executive producer of ABC’s “The Mayor,” a new comedy about a young hip-hop artist who is elected mayor of Fort Grey, California. Diggs’ own career in hip-hop and rap has also continued to flourish, both as a solo artist and in various groups. Now the beloved performer is making his feature film debut in “Wonder,” Stephen Chbosky’s endearing adaptation of R.J. Palacio’s book about a young boy, Auggie (an unrecognizable Jacob Tremblay), whose facial differences have made it challenging for him to find friends in fifth grade. As the boy’s supportive teacher, Mr. Browne, Diggs gets to fleetingly share the screen with a certain well-known Wookiee. Needless to say, the Force is strong with this movie.

Diggs recently spoke with about his approach to teaching, how experimentation with the form is essential to his music and why his memory of performing for the Obamas still brings him to tears.

The infectious energy that you brought to the role of Mr. Browne is the sort of quality that gets students engaged in the classroom. 

I was trying to mimic some of the great teachers that I’ve had in the past, and I also taught middle school for a while. Stephen and I talked a lot about the kind of energy that we wanted Mr. Browne to exude. From my own experience and from my mentors, I was able to find the energy that sustains the attention of a young person. Teaching is really about energy management. I always relate teaching to doing a rap show, which is also about understanding where the energy of your audience is and figuring out where it needs to go in order to tell the story you need to tell. 

How were you able to deal with the problem of bullying as an educator?

In my experience, it was certainly tricky. You have to immediately protect the victims of bullying and they have to feel safe to still participate in the classroom environment. Whatever kind of bullying it is has to get stopped immediately and you have to figure out how to continue to prevent it, which has become much more difficult these days. The bullying can continue when the students are not in each others’ presence. Social media would’ve destroyed me as a kid, but the kids today seem so much better equipped to deal with it because they’ve grown up in this environment. You also have to figure out the root causes of the bullying because the victims probably aren’t the only people who are struggling. There’s some reason why the other party has chosen to bully them. 

That’s a tough thing to navigate, especially if you’re in a situation where you’re not with the kids all day or you’re seeing them for only a couple periods. You don’t know what’s happening at home and you can’t always just call the parents. I have so much respect for teachers. Not only do they have the lessons that they have to get through—both the state-mandated lessons and the topics that they personally think are important to teach—they also have to monitor the well-being of their students and try to help guide them, for the time that they have them, to be good people. It’s an incredibly difficult job that is incredibly underpaid.

“Wonder” reminds us that the bullies are often the most insecure people of all.

At its core, the film is about the bravery that it takes to just show up and be yourself. That’s why I got so emotional when I watched it because it immediately transports you back to when you were a kid. We develop a whole series of ways to not feel things so that we can go about our day, but when you’re young, you haven’t really built those up or fine-tuned them as much. So every day, you are left with the choice of, “Am I going to show up and do a bunch of safe things, or am I going to show up and be the person that I actually am?” It is such a brave thing to do, and you are quickly reminded of that when you watch Auggie interact with the world. It opened me up to all the rest of the film’s emotions, and I was a wreck when I watched it.

You’ve mentioned how the child actors were so supportive of one another, particularly between takes while shooting a fight scene in the school hallway. Do you feel that the younger generations have the potential to be more open-minded than their predecessors?

There is so much information out there, and the great thing about the information age is the opportunity that it presents for empathy. We get to experience so many different kinds of people if we look for them. You can watch videos about or even have conversations with people in Africa and other countries that you couldn’t before. Kids are so versatile at navigating the tools of this age. If you've had a cell phone since you were four years old, this stuff is second-nature to you. Earlier this year, I was sitting in a laundromat and saw a little girl looking for her favorite videos on YouTube. She couldn’t speak yet, and didn’t know how to type the words in, but she knew how to go into the search history and find the complicated URL that she was looking for. It blew my mind. Kids can find anything. It’s so easy for them.

I love how your hip-hop/rap group, Clipping, has been tirelessly experimenting with the form in its innovative tracks. 

Hip-hop is an art form that was birthed from the idea of sampling, which really happened in a vacuum. When you’re not being taught how to play an instrument, you can go through your parents’ record collection and figure out a new way to utilize portions of their music. In that sense, hip-hop has always been about experimenting with the form. My producers in Clipping, Jonathan Snipes and Bill Hutson, and I are fairly academic in the way that we think about things. We have a ton of conversations about our musical structure and what we are referencing based on that. We discuss what the lyrics will reference and whether there will be formal restraints on them, though there are always thematic constraints on the lyrics regardless. That’s the way I grew up making music, and it bleeds into everything I do. 

My favorite aspect of most projects is the structural part of it. I love how “Wonder” doesn’t throw away the perspective switches that happen in the book. It’s such a literary thing to do and such an impressive thing about the novel. Stephen’s insistence to view the same events from multiple perspectives is one of the big reasons why I was onboard with the project. I thought it was so cool how he honored the literary structure of the piece, which is difficult to do onscreen. Once you know the structure of a thing, the fun lies in how you can play with it. We think of Clipping as simply a rap group, but we never stop experimenting. I’m always making choices that are outside the parameters of the work.

Experimental scores are in vogue now, particularly in the realm of horror films. What has it been like to compose the score for your show, “The Mayor”?

The two guys I work with in Clipping are both pretty accomplished in the film score world. Jonathan and Bill both did the score for “Room 237,” the documentary about “The Shining,” and Jonathan has done a bunch of horror film scores, so he comes out of that tradition. Getting to work with them on “The Mayor” was so great because, between the three of us, we have a vast regional understanding of how hip-hop works. A lot of the fun for us is thinking about the form of what music sounds like in northern California, which is where we’re from. We take those formal elements and try fitting them around what a particular episode is about. We’re also creating new theme songs for each episode. For the Halloween show, we had a friend scratch one of those old records that contained spooky sound effects. In place of a familiar vocal sample like someone from the Bay Area going, “Bwahwahwah,” we had me laughing, “Bwahahaha,” Vincent Price-style, and looped the sound. It’s just another opportunity for us to play with form.

The premise of “The Mayor” has become an increasingly topical one in an era where entertainers such as Lin-Manuel Miranda and John Oliver have proven to be better educators than our news media and more honest than our politicians.

“The Mayor” really came about after its creator and show-runner, Jeremy Bronson, received a voicemail from his father saying that he was voting for Trump purely out of frustration with the political system. It hurts even more listening to it a year later, and it inspired Jeremy to tell the story of a political outsider who could actually motivate people to create change in their communities. You can do so much by getting involved with local government. Our democracy feels broken particularly on a national level, but when you look locally, you find people like Michael Tubbs, the young mayor of Stockton, California. He just started an initiative partnering with Facebook and a lot of other tech industries in Silicon Valley, where there is lots of money to go around, to produce a $500-a-month stipend, restriction-free, for residents of his town. He created it to see what kind of business it would bring and what it would free up citizens to do as artists or educators or new parents. Perhaps it could allow one parent to work while the other stays at home to take care of their kid. 

Tubbs is 26 years old and is thinking about things in a different way, which is what you would hope for from an outsider. Trump got elected because people were sick of seeing things done in the same way. Unfortunately, the side that won, in this case, also disliked progress in terms of racism and sexism, and were likely sick of seeing people of color all over the place. Our show is about outsider politics on a local level and in many ways, its goal is the same as that of “Wonder”—to promote kindness and empathy.

I can only imagine how thrilling it must’ve been to perform songs from “Hamilton” for the Obamas at the White House.

It was unbelievable, but in fact, the most incredible part of the day occurred before we performed. We spent hours with inner city kids doing workshops where we helped them create “Hamilton”-style retellings of other historic events, and then they got to perform those for the President and First Lady too. Having that kind of access to the White House was ludicrous. I don’t think we’ll ever have a First Family like them representing us again. They were so open to everybody, and they made their house, which is so historic, open to all of us scrappy revolutionaries. You had young people, mostly of color, running around the White House while working with kids all day. It was incredible. I’ll never forget when Chris Jackson sang “One Last Time,” while standing under the portrait of his character, George Washington, as Barack Obama—in his last term—watched from the front row. I still get teary-eyed thinking about it.

Matt Fagerholm

Matt Fagerholm is the former Literary Editor at and is a member of the Chicago Film Critics Association. 

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