A man of many talents: Award-winning actor Jeremy Piven takes on stand-up comedy

From the time he was a child, Jeremy Piven’s parents, Byrne and Joyce Piven, assured him he was enough.

The “Entourage” actor, who grew up in Evanston, recalled his mother telling him: “Don’t doubt yourself; don’t get in your own way; you’re enough.”

“As a kid that is incredibly empowering,” said the three-time Emmy Award-winner, whose acting career spans nearly 40 years.

Piven continues to heed his mom’s advice, which served him well eight years ago when he embarked on a second career as a stand-up comedian. In fact, stand-up brings him back to Chicago Friday, June 6, for a headlining gig at The Vic Theatre as part of his U.S., Canada and Australia comedy tour.

A performer since the age of 8, Piven’s first acting coaches were his actor/director/educator parents, who in the early 1970s founded the Piven Theatre Workshop, an Evanston theater company and training center whose students included Jeremy and his sister Shira, John and Joan Cusack, Aidan Quinn and Lili Taylor, among others.

“We were so incredibly lucky and we had no idea,” he said. “I thought every kid in the world was onstage with their family having fun, making people laugh.”

The Second City veteran and lifelong improviser always had an interest in stand-up, which he calls “the mixed martial art of comedy.”

“Every project I’ve done as an actor I always pitched ideas and jokes. Sometimes they’re welcomed with open arms and sometimes they’re not,” said Piven, who, in addition to “Entourage,” starred in the PBS series “Mr. Selfridge” and co-starred on “Ellen” and “The Larry Sanders Show,” among others.

In 2017, when the stand-up opportunity arose, he took it. In a sense, he had been preparing for it all his life. As his Shakespeare-quoting mom said: “the readiness is all.” Piven proves the point.

“All those years prepare you so you might have a chance to be ready in the moment to address something that’s coming your way,” he said. “The harder you work, the easier it seems.”

As he prepared for his second career, a fellow comedian told him doing stand-up would make him a better actor. Piven was skeptical, but the comedian was right.

“Acting is a momentum sport,” he continued. “In between jobs you’re sitting idle … I was doing stand-up, I was performing my bits, improvising. Then I went back to acting.”

“Stand-up made me a better actor because I had no rust on me by the time I went back to the set,” he explained.

In comedy, as in acting, there’s no subject he won’t address, no role Piven won’t consider.

“My mother had this great rule growing up: You can say whatever you want as long as it’s funny,” recalled Piven, who routinely ran lines with his mom, including some of the more vulgar dialogue uttered by his most famous character, “Entourage’s” foulmouthed superagent Ari Gold.

Piven’s parents taught him to never judge the characters he plays.

“You play them fully,” he said. “You invest as much integrity as you can because no one is the devil in their own story.”

Piven continues to balance stand-up and acting. He has several feature films in the works, including the psychological thriller “Past Life” and a horror thriller titled “I am Your Driver.” in which he plays the titular role.

But the role he’s most proud of is that of Harold, a Jewish tap dancer recruited to perform for Adolph Hitler in 1930s Berlin in “The Performance.” Adapted from Arthur Miller’s short story and directed by Shira Piven, the project was suggested by Joyce Piven, who died in January at age 94. Fifteen years ago, she mentioned Miller’s story to him and remarked he’d be perfect for the lead. He subsequently spent 15 years learning to tap dance.

“It was no small thing she handed me,” said Piven, praising both his mom and his sister for what he described as a labor of love that represents “the best work of my life.”

“It’s part of our legacy, this film,” he said.

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Jeremy Piven: Live Stand-up Tour

When: 7:30 p.m. Friday, June 6

Where: The Vic Theatre, 3145 N. Sheffield Ave., Chicago, jamusa.com/venues/the-vic

Tickets: $47.89-$79.78