On Sunday, Oct. 28, Ann Randolph will perform her one-woman show Loveland at the Katharine Cornell Theatre. The show, like all her shows, is based on real life.

“The tale came out of traveling back and forth from Loveland, Ohio to Los Angeles,” Ms. Randolph said. “My dad was dying and my mother had a stroke and then took up drinking for the first time in her life.”

If this sounds like subject matter one usually runs in the opposite direction from, consider this.

“The show is hilarious,” Ms. Randolph added. “It’s already too hard, might as well have a good time.”

For Ms. Randolph, a stand up comedian and former member of the Groundlings, a Los Angeles-based sketch comedy group where Will Ferrell also got his start, comedy is not an escape from the darker subjects of life. Rather it is the conduit, a way to dig even deeper.

“Comedy sneaks up on you. You’re laughing, laughing, then crying,” she said.

Ms. Randolph began creating her autobiographical one-woman shows soon after college. Following graduation, she traveled to Alaska hoping to build up an arts nest egg of sorts by working in the fishing and canning industry. This was in the late 1980s when Alaska was a Shangri-la for college kids and recent graduates. Tales of earning $20,000 in just a few months circulated throughout the fraternity pub rooms and college bars in most of the lower 48 states.

Soon after she arrived in Alaska, though, the Exxon Valdez ran aground and she got a job “making $2,000 a week cleaning oily rocks.” Then she went to work on an Exxon research vessel.

“I spent the next nine months out at sea on a small research vessel with 14 men with eighth-grade educations. I was the only woman, and we only made it to port once a month. No phones, no mail — only 24 hours of porno films shown in the galley.”

For most this would have been a nightmare. For Ms. Randolph it became material for her first one-woman show.

Another show, Squeeze Box, which was produced by Mel Brooks and Ann Bancroft and for which a movie is in the works, was also based on real life.

When Ms. Randolph was in college she didn’t live in a dorm, an apartment or commute to school from her parent’s house. She saved money on rent by living at the Athens State Mental Hospital. In exchange for a free cot to sleep on, Ms. Randolph took the patients on small road trips and performed plays for them.

— Ann Randolph.

Combining this experience with a later one where she worked at a women’s homeless shelter, Ms. Randolph wrote Squeeze Box which, among other awards, won the best solo show in Los Angeles in 2002.

To get at the humor of these not normally knee-slapping subjects, at least not on the surface, Ms. Randolph creates alter-egos. For Loveland she plays 12 characters and the central character, herself, you could say, is “emotionally true in what I think but wouldn’t express.”

In other words, the character is her free-wheeling id, saying things the more civilized Ann would never say out loud.

“This character is out of control sexually,” added Ms. Randolph.

Loveland was first produced in San Francisco in 2009.

“It was like writing a piece of music that was way too hard to perform,” she said. “The characters were originally caricatures.”

After one of the early performances, a student of her’s approached her after the show. “It was so cool to see my teacher fail,” the student said to her.

“To go on after that was tough,” Ms. Randolph said. “But by the time the critics came, it was cooking. It just took a while to trust it was in my body.”

The show heads to the Arena Stage in DC in 2014 and then to New York city.

To see the result of Ms. Randolph’s many years of hard work, one only needs to buy a ticket for Sunday’s show. To learn how to apply her technique to one’s own life and material, Ms. Randolph will also be offering a Write Your Life workshop held on Saturday and Sunday.

“Whenever I perform, I build in a workshop,” she said. “I’m a community person and it’s too lonely just doing the show.”

In fact, it was her skills in teaching a workshop that brought Ms. Randolph to the Vineyard. Catherine DeGrandpre, who lives in Chilmark and teaches math at the regional high school, took one of Ms. Randolph’s workshops at Kripalu in the Berkshires and immediately afterward asked if she would come to the Vineyard.

The workshop is not just for those whose ultimate goal is to actually perform a piece, Ms. Randolph said.

“We all want someone to hear us,” she said. “There’s something to sharing your deeper story that I think is healing.”

Ms. Randolph also makes sure there is time after each performance.

“There is a raw openness after the show,” she said. “Seventy per cent usually stay. People want to tell me their story. So I create mini-workshops after the show.”

Loveland will be performed for one night only, Oct. 28, beginning at 7:30 p.m. at the Katharine Cornell Theatre in Vineyard Haven. Her workshop will take place on Saturday, Oct. 27, from 10 a.m. to 6 p.m., and Sunday, Oct. 28, from 10 a.m. to 1 p.m. Visit brownpapertickets.com.