Daveed Diggs shares his journey to ‘Hamilton’ and Broadway, plus what it means to be an artist

Written by Danielle Chiriguayo, produced by Angie Perrin

Daveed Diggs portrays Federick Douglassin Showtime’s “The Good Lord Bird.” Photo by William Gray/SHOWTIME.

Six years ago, actor Daveed Diggs went from being a substitute English teacher in middle schools to starring on Broadway in the critically acclaimed musical “Hamilton.” 

Diggs played a dual role in the Broadway sensation, appearing as both Thomas Jefferson and Marquis de Lafayette. That won him both a Tony and a Grammy award. From there, the job offers rolled in. 

Today, he has roles on ABC’s “Black-ish” and “Mixed-ish,” and TNT’s “Snowpiercer.” His 2018 film “Blindspotting” — which he co-wrote, produced, and starred in — has been adapted into a TV series on Starz that debuts next month. 

KCRW talked with Diggs about his life before “Hamilton,” acclimating to  Broadway, and the balancing act between being creative and fulfilling personal needs.. 

An early career as an educator 

Diggs first started performing on stage in the seventh grade, something he continued at Berkeley High School. But surprisingly, he never took part in a musical until “Hamilton.” 

“There were plays in the fall, and then in the spring, it was musicals. But I was always running track in the spring. So I had to do the plays in the fall and then run in the spring. …. I didn't really like singing in front of people.”

Part of that hesitation stemmed from never being exposed to musicals growing up in the Bay Area. “It wasn't really part of my imagination, you know? I don't think I even ever saw a show on Broadway until I was doing workshops for ‘Hamilton.’” 

After graduating from Brown University in 2004, Diggs says he went back home to Oakland, where he worked in arts education and performed on stage. He also developed spoken word-based curriculums for local students. All while writing his own rap songs.

Diggs says he’s stayed just as busy now as in the early days of his career.

“Very little in terms of how we live our lives has changed. But just so many more people watch us do it now. But the hustle feels almost exactly the same. I'm sitting in my recording studio right now. When we finish this, I have songs that are due. And yeah, and then I'll wake up early in the morning and be on set with ‘Snowpiercer.’”

From the small stage to The Great White Way

While workshopping “Hamilton,” Diggs says he was on tour with “Word Becomes Flesh,” a choreopoem by Marc Bamuthi Joseph, as well as his band Clipping. 

“I just assumed they'd replace me by the time they went to Broadway, because they had all a lot of seasoned Broadway veterans who were friends of theirs, but then that didn't happen.”

He says navigating through the brand new world of Broadway was different than what he was accustomed to.  

“It's its own ecosystem. And it is beautiful in a lot of ways [with] a lot of the hardest working, most talented artists I've ever been around. But it also is so blind to the outside world. It thinks that way more people care about it than do.”

But Diggs says working on “Hamilton” felt similar to his earlier projects. That’s due in part to working alongside people he considered friends.

“I was in Freestyle Love Supreme. Those are all my friends. And so it was just making stuff with my friends, which is the same thing I’ve always done. ... And we like to make art projects together. And ‘Hamilton,’ at the end of the day, felt like one of those.”

He adds, “It was super weird that so many people wanted to see it. … It's sort of the dream of what you always think when you're making stuff with your friends. Like, ‘It'd be crazy if anyone ever was gonna see this, but they probably won’t.’”

The 10-year journey to “Blindspotting”

Alongside longtime friend and collaborator Rafael Casal, Diggs started writing Blindspotting a decade ago. At the time, Jess and Keith Calder approached Casal after watching videos of his poetry on YouTube.

“That was sort of this 10-year journey of us learning how to write a movie, thinking we had a draft that was a good idea, and trying to figure out how to shoot, attaching directors to it, and going on scouts up in the bay, and then [having] the funding fall apart. ... It took 10 years to write that movie, in part because it was hard to get produced. But also because it took us that long to learn how to write a good movie.”

Being a creative while making the bills

Diggs says the unknown part of the creative process calls to him. But oftentimes, he says that as an artist, he has to recognize the balancing act that comes with pursuing creative projects and fulfilling his own needs.

“Just because something is commercial doesn't mean it's not creative. … If  a check presents itself and you need the check, you should take the check,” Diggs says. “I would take the check and then use that money to not stress for the next few weeks. You can make better art. It's really hard to make good things when you're stressed out.”

Diggs says as an artist, finding oneself can be tricky, but a necessary part of growing as a performer. 

“There’s a balance and the whole hustle is trying to find that balance, and understanding that it keeps changing as you get older and your values keep shifting, and just allowing yourself to be a person whose needs and wants and values change over time.”

Connecting to a role

Portraying historical figures wasn’t initially in the cards for Diggs. Not only were they roles he wasn’t particularly interested in, but after one fateful audition where he was told he was “too contemporary” for a role, Diggs didn’t see them as a viable option. 

That changed through the course of his career, thanks to shows like “Hamilton." And in 2020, Diggs portrayed Federick Douglass in the Showtime miniseries “The Good Lord Bird.” 

He says the role was an opportunity to dive into autobiographies and learn as much as he could about Douglass. The more he learned, the more he found similarities between the historical figure and himself. 

“The thing that stuck out to me was that here's a brilliant man who is … creatively mining his past in order to rally people around this idea of emancipation, and for financial gain,” Diggs says.

He adds, “That was the thing I could all of a sudden really relate to: having a very, very public persona and the trickiness of navigating that and the value of that — how much good he can do as this very public person and how at odds that can be sometimes with what he wants to do.“