Jon Michael Hill sits in a third-floor conference room inside Steppenwolf Theatre’s sprawling Lincoln Park building, meticulously studying the script for his role in the world-premiere play “Leroy and Lucy.” He’s too engrossed to notice someone entering the room.
Glenn Davis, co-artistic director of Steppenwolf and a close friend of Hill’s, said that the Tony Award-nominated actor’s deep level of preparation has always been a key piece in the pre-production process.
“He is a hard worker,” said Davis. “He’s very diligent. He never wants to be caught unprepared. He always wants to feel like if something is thrown at him on the spot that he can handle it.”
Hill is studying for his upcoming role in “Leroy and Lucy,” which playwright Ngozi Anyanwu based on the life of Delta blues legend Robert Leroy Johnson. According to the myth, Johnson — whose professional recording career only spanned seven months — made a deal with the devil to trade his soul in exchange for becoming a blues legend.
A large part of the myth surrounding Johnson is how quickly he mastered his craft. This somewhat parallels the career of Hill, 39, who joined Steppenwolf’s ensemble while still a theater major at the University of Illinois Champaign-Urbana.
“Outside of the original members,” said Davis, “he’s the youngest person to be invited into the company.”
Hill recalls not fully understanding the magnitude of that moment. “When I auditioned for the first play here, I had heard about Steppenwolf, but I had never seen anything here,” said the Waukegan native, who started doing theater in elementary school. Just before his senior year of college in 2006, he landed a role in “The Unmentionables,” directed by Anna D. Shapiro (who later won a Tony for directing “August: Osage County”).
By the end of his senior year of college, he had been asked to join Steppenwolf’s ensemble, a fast turn of events for someone who treated his first audition there just as he would any other.
“I think that helped, not having the idea of this big giant looming over me when I first walked in the building. But once I joined, I knew it was going to be a huge shift in my life,” said Hill, having now put down the script in the conference room. “Having an artistic home for a young actor just getting out of school is just unheard of. You can’t ask for a better situation.”
The next career turn came two years later, in 2008, when Steppenwolf ensemble member and powerhouse Chicago playwright Tracy Letts cast Hill in a lead role in his play “Superior Donuts.” That show, about a former 1960s radical who runs an Uptown doughnut shop with the help of his young assistant, transferred from Steppenwolf to Broadway.
“Tracy [Letts] was like, ‘Look, there’s a million ways these things fall apart,’” said Hill, “So I tempered my expectations. But then, a year later, sure enough, we were on Broadway, and then television casting directors came and saw that show.”
Hill’s performance on Broadway earned the young actor a Tony nomination. And the TV casting directors were from ABC. They took Hill to lunch and said they wanted him to be in an upcoming pilot. At the time, Hill didn’t believe them.
But the very first TV show he auditioned for was “Detroit 1-8-7,” a drama about the Detroit Police Department’s homicide unit. “We went through the whole pilot deal, where you go to LA and you audition for the executives. And you sign a deal before you get the job, with all the paperwork — seven years of your life — and somehow, it all worked out.”
Hill landed the role and found himself working with actor Michael Imperioli (“The Sopranos,” “Goodfellas,” “White Lotus”).
“Man, it was — it was special,” said Hill. “I didn’t know anything about television, so I just sat there on set and watched Michael Imperioli and how he was with everybody. He was like my mentor, and I sort of modeled my on-set behavior after him. He had such a good zen tone in a very chaotic business. And that show was nuts.”
Asked if his quick rise to Broadway and television success is typical for young actors, Hill only laughed and said humbly that “every actor has their own journey.”
A year after “Detroit 1-8-7,” Hill was cast in the CBS hit show “Elementary” (2012–2019), where he appeared in 153 episodes over seven seasons.
Hill says even with his past success, he is still hungry, but he manages his expectations, which has become harder as he’s gotten older.
“I never really used to have expectations when I was young,” he said. “So everything that was happening, I sort of took it as it came and was very grateful. But I wasn’t disappointed often, because I didn’t expect things to happen. And I think maybe the older you get, the harder that gets.”
Last spring, Hill landed the lead role in Brandon Jacobs-Jenkins’ world premiere play “Purpose,” a family drama about a prominent Black political dynasty. That show, critically acclaimed in its Chicago premiere this past spring, is now headed to Broadway.
Speaking of expectations, does Hill see “Leroy and Lucy” as his chance — should he accompany the show, as is likely — to win the Tony that he was so close to winning early in his career?
“I can’t think like that, not at all,” he laughed. “Denzel [Washington] is on Broadway, Jake Gyllenhaal is on Broadway — there’s a slew of other incredible actors that are going to be doing roles. I’m gonna go and try to do what we did here, which was bring the New York audience an exceptional, challenging, hopefully transformative work that gets people to leave the theater asking questions. I want to make them feel something.”
But before Hill heads to New York, he must conquer the part of Leroy, which requires him to play music onstage. For weeks, Hill has been learning to play harmonica and brushing up on his guitar skills.
“Robert Johnson’s style is unlike anybody’s,” said Hill. “It sounds like two people playing guitar. To be able to replicate that technique is a challenge.”
The show’s director, Awoye Timpo, describes Hill as “very focused, super intentional about everything that he does.” She says he also has a silly side. “Every now and again, he will bust out a great dance move or a silly voice or something. He’s very playful, actually,” said Timpo.
Given Johnson’s roots in the Mississippi Delta, the Steppenwolf role also requires dialect coaching.
“I feel like he is being stretched in all kinds of directions,” said Timpo. “But he has such a mastery of his own craft and his own work process that I think he’s just delighted and excited to explore every possible crevice of this play and of this character.”
Observing Hill on set, Timpo is impressed by his ability to embody a character. “He goes on a very deep dive to submerge himself into the world, and he doesn’t want to leave any corner or any little place where there’s possibility for creation,” she said. “He doesn’t want to leave that unexplored, which is what makes him such a great actor.”