Presented with the basic premise for what would later become the defiantly woke, Pulitzer Prize-winning, billion dollar-grossing Broadway smash hit Hamilton in 2013, rapper-actor Daveed Diggs reacted strongly to the material—just not in a good way.

“I said, ‘That’s a terrible idea,’” recalls Diggs. “If someone says to you, ‘Hey, here’s a rap musical about Alexander Hamilton,’ the elevator pitch of that show is not good!”

Realizing he’s implicitly shitting on Hamilton mastermind Lin-Manuel Miranda, the performer clarifies: “There was never any doubt that Lin could pull this off. Immediately upon hearing the music or reading the scenes, it becomes clear that it’s a wonderful idea. But if you ask me if I think this is a bad idea? I still think it’s a bad idea.”

Diggs, of course, went on to originate the production’s dual dead-white-guy role of Thomas Jefferson/Marquis de Lafayette, picking up a best actor Tony and a Grammy for his risk—all while firmly entrenching himself within America’s cultural consciousness thanks to his rapid-fire MC skills and Sideshow Bob-esque head of corkscrew curls.

Which is a pretty positive outcome for a guy who just a few years earlier had regularly slept on the 2 train—Manhattan’s Seventh Avenue express—during his starving actor days. He was scraping by on just $100 a week in unemployment benefits and getting rejected time and again during “soul-crushing, nonsense” auditions. “I didn’t have a job or an income source,” Diggs says. “I was going to these big cattle call auditions. I’d leave those things and go hang out with friends. I was young and invincible. Sleeping on the subway was fine.”

I didn’t have a job or an income source. I was young and invincible. Sleeping on the subway was fine.

But in 2016, after two years and somewhere in the neighborhood of 700 performances beneath Hamilton’s blinding cultural spotlight, the Oakland-born multi-hyphenate—who was recruited to run the 110 meter high-hurdles at Brown University but graduated with a degree in theater—decided it was time to branch out. “I knew it was time for me to go,” he says. So in recent months, Diggs has turned his attention to an almost mind-boggling array of eclectic projects.

“I wanted to keep working,” explains Diggs. “I didn’t know how long it would be before I worked again. And I was also aware that something had happened that had given me a visibility in this business that is pretty rare—especially for a person doing theater. I was confident in the people I had chosen to work with. But I was nervous: how do you not make the wrong decision? It’s such a fickle business.”

In addition to racking up character arcs on such shows as Netflix’s The Get Down (as the show’s narrator, a hip-hop superstar), Unbreakable Kimmy Schmidt (a university philosophy student and possible Kimmy paramour who, yes, busts a rhyme on camera during the show’s third season) and Black-ish (as Tracee Ellis Ross’ pompous, croissant-chomping hipster brother Johan), Diggs has also been touring with his experimental/underground noise-rap group Clipping.

On November 17, Diggs will mark his film debut with a supporting role as an English teacher alongside the likes of Julia Roberts and Owen Wilson in Lionsgate’s YA novel adaptation Wonder. “I was a teacher for many years before anyone knew who I was,” Diggs notes. “So it felt close to home. I still teach workshops and try to work in education whenever I can. I think teaching is one of the most important jobs you can do, so I jumped at the opportunity to portray a really great teacher.”

Then there’s his pivot to the other side of the camera with the new ABC sitcom The Mayor for which the 35-year-old serves as executive producer. After his recurring role on Blackish, and still relatively burnt out by his long Hamilton co-starring run, Diggs was reluctant to sign on for the “grind” of a multi-year commitment of a starring role but warmed to the idea of calling shots creatively (what’s more, he and his Clipping band mates Jonathan Snipes and William Hutson are creating the show’s original music). Debuting to generally positive reviews earlier this month, The Mayor (Tuesdays at 9:30 ET) follows an aspiring NorCal hip-hop artist (Brandon Michael Hall) who runs for political office to jump start sales of his mixtape—but unexpectedly wins the election.

“Setting it in Northern California means it would sound different than any other part of the country or even someplace as close as Los Angeles,” Diggs notes. “Because of where he is, [the main character] Courtney Rose will be more influenced by E-40, Mac Dre and Keak da Sneak than, say, Jay Z, Nas and Biggie. I was excited to work on a show that honors those distinctions and I think this specificity adds authentic to the character and the town.”

And as if his dance card weren’t yet already full enough, Diggs is set to star in TNT’s futuristic sci-fi series Snowpiercer as a prisoner barely surviving on a gigantic, fast-moving train that continuously circles the globe years after civilization has been wiped out by a post-apocalyptic ice age. “I don’t think any performer wants to be pigeonholed,” Diggs says with a shrug. “And I’m a sci-fi nut. It’s exciting. It’s one of the reasons I’m in this business: I’m not very good at doing the same thing every day!”