Writer and performer Ann Randolph has lived an amazing life. In college, rather than paying to live in a dorm, she lived in the schizophrenic unit of a state mental hospital in exchange for writing plays with patients. She worked the graveyard shift at a homeless shelter for minimum wage for 10 years. And she once lived on a boat in Alaska for a year with 14 men from Louisiana with whom, at first, she appeared to have nothing in common.

A writer from a young age, Randolph joined The Groundlings, an improv and sketch comedy theater in Los Angeles, after college. “I was very interested in creating outrageous characters,” she says, but her personal style evolved into “combining comedy and the human condition.” Drawing from her own life, she began writing and performing solo shows. “Whatever I’m struggling with I create a show around it,” she says, adding, “I find writing is very healing, very powerful.”

She wrote Squeeze Box about her time working at the homeless shelter and performed it in “a crappy theater” she rented in L.A. “That’s when Mel Brooks kind of discovered me,” she says. “He and his wife [Anne Bancroft] showed up.” One of the characters Randolph played was a prostitute addicted to crack, a character inspired by someone she met at the homeless shelter. “Anne Bancroft loved that character,” she says. “She wanted to make [the show] into a movie and play her on Broadway.” Brooks and Bancroft whisked Randolph away to New York City where they produced Squeeze Box off Broadway in 2004. “It was a big shift for me,” says Randolph, who went on to tour with the show.

Bancroft passed away in 2005 before they were able to adapt Squeeze Box into a film. Then Randolph’s own father and mother died. “So,” Randolph says matter-of-factly, “the next show was a comedy about death.” Titled Loveland, she performed it at Arena Stage in Washington, D.C., in 2014. A theater critic for the Washington Post called it “inappropriate in all the right ways,” which struck Randolph as the perfect title for her next show.

“I’ve been told I’ve been inappropriate my whole life so I just love that title,” she says. “I believe that there’s room for appropriateness and inappropriateness, and it can be done in an illuminating and hilarious way.” Most important to her is what is true. “If we can’t speak our truth we can’t be authentic in our lives,” she says.

Virginia Organizing has invited Randolph to perform Inappropriate in All the Right Ways as the headliner for its Night of Comedy and Storytelling for Racial and Social Justice, an event that will include Susan Bro (mother of Heather Heyer), former 5th District Representative Tom Perriello and local hip-hop group Sons of Ichibei.

Randolph’s show is a “story about resiliency” that chronicles her life “as a creator,” she says. At one point in the production, she invites willing audience members to share their stories. “How incredibly cathartic it can be to speak something you’ve been holding on to for a long time,” Randolph says.

The show also raises the question “Can we see ourselves in another?” and illustrates the camaraderie Randolph found in people different from herself. “You may start out thinking you’re different,” she says, “and in the end you’ll see where you’re united rather than divided. It comes from listening to people’s stories and dropping judgment and preconceived ideas.”

What’s one thing she believes helps people listen? Humor. “Sometimes when we hear someone’s strong point of view in a preaching voice we tune out. But if there’s humor there we’re more receptive and open,” she says.