Award-winning writer and performer Ann Randolph brings her spin on life’s little challenges to the Vineyard with her solo show, Loveland. Ms. Randolph takes the audience along on a cross-country flight described as both hilarious and deeply human. She will offer two shows at the Katharine Cornell Theatre in Vineyard Haven, one this Saturday beginning at 7:30 p.m. and another performance next Saturday, July 13, at the same time.

In an interview from the Berkshires where she is teaching a writing workshop, Ms. Randolph provided some insight as to where she gets her material. In a nutshell, she said she draws on her life experience and then allows herself to unleash the unspeakable. The main character in Loveland, Frannie Potts, she explained, is an exaggerated version of all those things typically hidden within us.

“I created Frannie Potts as a sort of alter ego,” she said. “She’s not politically correct.”

Ms. Randolph comes from a small town, Loveland, Ohio, and her play of the same name sprang from the trips she made back and forth from Los Angeles while her father was dying. Her mother had a stroke and took up drinking. Luckily, Ms. Randolph said, her family is supportive of her work.

“You know those privacy curtains they have in hospital rooms? Well, I’d pull the curtain back and forth and perform the play for my dad,” Ms. Randolph said. Audience members have often told her they think they see part of her father in the play. “They [her parents] definitely had a sense of humor when I was growing up, but they did not let me major in theatre. They provided emotional support but I think they worried that I’d be destitute.”

She managed to sidestep dorm life during college by sleeping on a cot in a state mental hospital. “I heard they would allow up to six students to live there for free,” Ms. Randolph explained. “And I didn’t have a car and they let me drive the state van. I just had to drive some of the residents around. I had read King of Hearts and I thought that was where all the geniuses lived.”

She wrote and performed plays for the patients in the mental hospital.

After college, she read a newspaper advertisement that claimed you could earn $20,000 cleaning fish in Alaska so she bought a one-way ticket hoping to earn enough to move to New York and continue working on her plays. The ad wasn’t exactly legitimate, but she did eventually earn the $20,000 she needed to move to New York city.

“I squatted in a gold miner’s cabin for awhile,” Ms. Randolph said. “Eventually I lied and told them I was a college instructor.”

Her penchant for free room and board continued there. She put an ad in the New York Times offering tutoring or companionship in exchange for free room and board. “I ended up living in a penthouse with this 90-year old Jewish man who just wanted someone to talk to,” she said.

Ms. Randolph eventually took a job in a women’s homeless shelter writing plays when she wasn’t working. She said she didn’t mean to stay at the job long, but it stretched to nearly 10 years. It was that experience that birthed her award-winning, one-woman play Squeeze Box. As often as she could, Ms. Randolph would save up enough money to rent a place to perform her play off-Broadway. One night Mel Brooks and Anne Bancroft came to see it. She connected with the couple and worked with them for a year and a half whittling Squeeze Box down to 80 minutes from its original two and a half hours.

“From that point on, I’ve been on the road doing what I love,” she said.

Ms. Randolph describes Loveland as an hysterically funny play about death with some sex thrown in. She said it isn’t a stretch for her to pull off playing a dozen characters, even a sex scene, by herself. Ms. Randolph honed her comedic skills over the years doing improv with people like Will Ferrell and Cheri Oteri. She culls her characters from people she’s met throughout her life, impersonating them with ease, flowing in and out of characters during a performance.

“It’s easy for me to find the funny in the most horrific experiences,” she says. “It comes naturally to me. Then, I can switch right into teacher mode after my performance. People usually want to stick around and talk after the show so I offer a mini-workshop after the performance.”

Ms. Randolph said she finds it a bit isolating traveling and performing, so she adds teaching into the mix by offering writing workshops wherever she’s performing. “I love to see people share something they’ve been holding onto, to watch them just let it go,” she said. “I get blown away by what happens at the workshops.”

While Ms. Randolph is performing on the Vineyard, her down time will be spent facilitating a four-day workshop, Write Your Life, at Island Co-Housing in West Tisbury beginning Sunday, July 7 at noon. She will lead writing exercises, group discussion, improvisation and other means to teach participants the skills they need to transform their own stories into memoir, whether it be through performance or writing. Essentially, she said, she gives them permission to share things they’ve never shared before.

She is coming to the Vineyard through an invitation from one of her students, Catherine DeGrandpre, who teaches math at the regional high school. Ms. Randolph said she is excited to both perform and teach this coming week. She visited with students at the high school when she was on the Island last year, she said. 
“It’s the Vineyard,” she said. “It’s so cool.”

For more information on the performance and the workshop, visit For tickets or to sign up for the writing workshop, go to