In 1961, during a snowstorm, Dick Gregory received a personal request from Hugh Hefner to perform at Chicago’s Playboy Club. Until then, the African American comedian had worked mostly at small clubs with predominantly black audiences where he was being paid an average of five dollars per night. His performance at the Playboy Club launched Gregory onto the national comedy scene, and, within the year, he was selling out nightclubs and making regular television appearances.

This pivotal winter night in Chicago is a key moment in Turn Me Loose, Gretchen Law’s new play about Gregory’s life and career, directed by John Gould. Scandal star and Emmy winner Joe Morton stars as the famed comedian as he takes the Playboy Club stage with a hint of nervousness, starring out at his new, predominantly white audience that evening in Chicago.

Every night as Morton heads to the Westside Theatre, where the show is running through July 3, the actor prepares to inhabit the mind and body of the historic funnyman and activist. Morton has a ritual of sorts: He puts Gregory’s cufflinks on, then his watch and wedding band as he works through the script. “I’m preparing my body for what I’m going to put it through for an hour and half,” says Morton. He performs Turn Me Loose alongside John Carlin, but much of the play feels like a one-man show.

Law’s play blends Gregory’s real-life stand-up with more intimate moments backstage; we see the performer and the man behind the comedian—a civil rights activist, a father and husband and a man passionate about health, politics and humanity.

Performing Turn Me Loose is exhausting, says Morton. It’s 90 minutes filled with tears, joy, laughter and a lot of history—the good, the bad and the ugly of it. Though much of it takes place in the ’60s, the show feels eerily relevant today. “I think one of the beauties of the play, and strangely one of the odd ironies of the play, is that here is a man who is talking about many of the things that we’re facing today, thirty years ago,” says Morton. “Everything from racial politics, to nutrition, to corporate greed…the Trumps of the world, how the rich people of the world are affecting the disproportionate.”

“They’re still happening today,” continues the actor, “which says a lot about what we need and how we need to heal ourselves as Americans.” In a recent interview, President Obama called Gregory one of his two favorite comics ever; the other was Richard Pryor who himself said, “Dick Gregory was the greatest and the first.” At 84-years-old, Gregory continues to be a prevalent rights activist and an important voice in the equality movement.

Like much of Gregory’s work, Morton sees Turn Me Loose as a call-to-action. “It’s asking the audience to take a look inside themselves to figure out who they are and what they can do,” he says. “No one is asking them to be activists 24/7…[but what is] the smallest thing that you can do? How much service can you give to your fellow human beings in the smallest possible way?” Morton says this is what ultimately makes the play so relevant, along with preserving Gregory’s meaningful legacy.

It was also one of the reasons Grammy winner John Legend became attached as a producer. “People like Dick Gregory, Paul Robeson, Harry Belafonte and Nina Simone show me what the definition of an artist is,” said Legend when he first announced his involvement. “It isn’t just to make art but to speak truth to what’s happening, speak beauty into the world, speak love into the world and also get involved.”

In preparation for the role, Morton read Gregory’s biography, watched countless YouTube clips of his stand-up comedy and listened to a lot of his recorded performances. He was also able to speak with Gregory on the phone. “We spoke for about two hours,” recalls Morton. “We ended up talking about our fathers, and the way we grew up and those kinds of things. I just really wanted to just hear his voice. I wanted to hear his attitudes about things; and I just wanted to let him talk—talk to me about anything he wanted to, it didn’t much matter.” The two also met in person twice, briefly.

Gregory is set to attend the official opening night May 19, which Morton predicts will be both “elating and terrifying at the same time.” “My fear,” he says, “is that at some point during the show—since I spend a lot of time dealing with the audience directly—I know I’m going to end up looking him straight in the face, and I have to figure out what to do about that.”

The Scandal star says one of the most satisfying things about returning to the stage is this first-hand interaction with the audience, something he doesn’t get from television acting. “The audience’s response is immediate...Especially if there are black people in the audience you’ll hear a lot of ‘Mm hmm,’ and that’s important,” he explains. “That carries me. That buoys me all the way through the play.”

Turn Me Loose officially opens May 19 and is scheduled to play through July 3 at the Westside Theatre Off-Broadway. Click here for more information and to purchase tickets.

Olivia Clement is a news and features writer at Playbill.com, specializing in the wonderful and expansive world of Off-Broadway. Follow her on Twitter @oliviaclement_.