“No one, not even me, is so obtuse that he doesn’t know when he’s doing wrong,” says Felonious Munk, writer and star of “Nothing to Lose (but Our Chains).” (Cade Martin/Cade Martin)

When a standup comedian starts talking about getting locked up, you instinctively brace for the punchline. So when Felonious Munk told his prison story to Billy Bungeroth, the director at Chicago's Second City comedy troupe began chuckling in anticipation.

Bungeroth soon noticed, however, that this was a true story, difficult to share. When Munk was done, Bungeroth said, "You should make that into a show."

He did. Munk transformed his experiences as a drug dealer, inmate and successful parolee into "Nothing to Lose (but Our Chains)," which starts Saturday at Woolly Mammoth Theatre. Plenty of jokes are in the final script, but the sobering reality of the first story Munk told comes through.

Munk, who grew up in Newport News, Va., as Dennis Banks, served six years of a 32-year sentence; he shot a man who had stolen his drug profits, and he carjacked a bystander's BMW. After he was paroled, he landed a six-figure job as a car salesman in Northern Virginia. When sales cratered during the 2008 recession, he reinvented himself as the stand-up comic Felonious Munk, best known for his appearances on Comedy Central's "The Nightly Show With Larry Wilmore" and in Woolly Mammoth's 2016 hit "Black Side of the Moon."

How could he tell that unlikely story in a two-hour stage play?

"I didn't want this to sound like my redemption story," he says. "I was able to change my life, but that doesn't change the fact that I caused harm to a lot of other people along the way, and they have a right to be angry about that. Just saying sorry doesn't cut it. I wanted to include those other perspectives."

The first line of the show is "Welcome to 'Nothing to Lose (but Our Chains).' As you all know, I'm Felonious Munk." The second line comes from Odinaka Ezeokoli in the role of Munk's conscience: "Arrogant! They don't all know that. And your name is Dennis." Ezeokoli is one of the four additional actors who play dozens of roles, many of them contradicting the author's version of events.

"Odinaka reminds us that no one, not even me, is so obtuse that he doesn't know when he's doing wrong," Munk says. "When we do the scene where I shot the guy who robbed me, we not only allow the robber to have his say but also the innocent bystander whose car I stole. It's not a hero's journey."

It's the journey of someone who spent his whole life wondering what might have happened if he hadn't been born to a 19-year-old single mother or if his mother had given him up for adoption to an upper-middle-class family when she had the chance.

"The idea we battled with," he says, "is how much of your life is fate; how much is your choice. . . . The statistics don't lie: The percentage of people in prison who were raised by single moms is very high. Maybe if my dad had stayed around, it would have different. Maybe if I'd had enough hugs as a kid, I would have been Barack Obama."

This month, the 45-year-old Munk is moving his wife and two children from Chicago to Brooklyn and then traveling to Washington. Meanwhile, he's working on a possible series for Comedy Central. "As much as I regret how things happened, I'm happy with where I am right now," he reflects, "so I wouldn't change what happened. But a lot of people that my life impacted might disagree."

If you go
Nothing to Lose (but Our Chains)

Woolly Mammoth Theatre, 641 D St. NW. 202-393-3939. woollymammoth.net.

Dates: Saturday through Dec. 31.

Tickets: $20-$69.