In her one woman show The Big Boot, writer Jenny Allen takes a candid look at the cancer diagnosis that turned her life upside down and sent her on a soul-searching journey through complex internal landscapes. Rather than wallow in maudlin bathos, the play combines wit, humor and insight to frame the illness in a humane context audiences can relate to.

Ms. Allen, a respected journalist with frequent contributions to Esquire, The New York Times, The New Yorker and Good Housekeeping, divides her time between New York and West Tisbury with her husband, illustrator and writer Jules Feiffer (the two collaborated on the book The Long Chalkboard in 2006). Her warmth, humor and sprightly personality belie the physical and emotional challenges that followed her 2005 diagnosis of ovarian and endometrial cancer.

The play, she says, is “about the effect this diagnosis and treatment had on my life, my kids, my family, the mayhem this causes inside you and how that affects everyone around you. It’s having to absorb the shock of it, the bitterness about having doctors not having been able to diagnose this sooner, the psychic pain of having a disease that’s serious and grave. It’s losing my sense of humor, being frightened, and that fear translating to a fair amount of anger at doctors and my predicament, and the attempt to regain the pleasure of life and a sense of equilibrium.”

Last summer Ms. Allen performed an early version of the show at the Vineyard Playhouse. Unbeknownst to her, Pulitzer Prize-winning director James Lapine and his wife, writer/filmmaker Sarah Kernochan were in the audience. After the show Mr. Lapine approached Ms. Allen to discuss working together to further develop the production.

“It seemed amazing to me he had taken interest in this,” says Ms. Allen. “I could hardly breathe, it was so exciting.”

Over the next year, Mr. Lapine encouraged Ms. Allen to take the emotional risks necessary to make the show a richer, bolder work of art. The process included readings at the New York Theater Workshop (the organization that nurtured RENT through its early stages) and a recent performance of the expanded show at The Hopkins Center at Dartmouth College. Through his sensitive direction, assisted by associate director Darren Katz, the show has evolved into a powerful and moving narrative that takes the audience for a ride through the fog of war that surrounds a cancer diagnosis and the subsequent medical treatment.

“People ask me if I’m in remission,” Ms. Allen says. “I don’t think that comes up for another couple of years for me. Life still hangs in the balance for me and probably always will. It’s a very terrible disease. It’s not like you’re ever really out of the woods, but you’re less in the woods after five years go by.”

While cancer might seem like a grim topic for a play, Ms. Allen uses wit and humor to keep the show lively.

“It’s very funny,” she says. “It’s a little harrowing but even the harrowing stuff, there’s humor in it. I hope the audience finds it funny and moving and has a good time. It’s not a lecture, it’s not a reading, it’s not a lesson. It’s hopefully a little work of art. I hope they take real pleasure in it. Even though the subject matter might be considered difficult, I hope it’s enjoyable on that meaningful level.”

As a writer, Ms. Allen says she was compelled to process the trying experience through the lens of artistic expression.

“If you’re a writer, you have to write these things down, or else they’re lost,” she says. “I have to have tried to shape this, otherwise it’s a chaotic series of events that happened to me. I would be very unhappy if I hadn’t’ done this.”

Ms. Allen is unflinching in her account of the illness, even when it involves taking a clear-eyed look at herself through the treatment process.

“You want to be careful not to tidy it up too much,” she says. “You don’t always want to make yourself the good guy, and the doctors are all bad guys. I wasn’t always so nice, and sometimes there were doctors who were nice who I thought were not being nice. I wasn’t always gracious about it. I was in a lot of pain, which made me very angry. It’s been hard but important to cop to that. I wanted to get to the bottom of why I reacted in certain ways. I felt bereft and fearful, and therefore angry. Why did I feel that way instead of going down on my knees and saying, ‘Thank you for the chance to be alive every day’? It took a long time to get there.”

Ms. Allen and Mr. Feiffer will celebrate their 25th wedding anniversary this fall. She is close to her stepdaughter Kate Feiffer and deeply devoted to her daughters Halley (a 23-year-old actress with film credits in You Can Count On Me and The Squid and the Whale) and Julie (13). In the show Ms. Allen describes aspects of her tribulations she withheld from her family out of stoicism and a desire to shield them from the painful details of the treatment.

“It may be more than they want to hear,” she says of the medical details. “There are some very scary images that they didn’t need in their heads at the time.”

In performing the show alone on a stage, Ms. Allen takes on the triple challenge of writing, acting and recounting her own intimate life story. She praises director James Lapine for guiding her through the process.

“I would not have had the courage to go as deeply into this without being nudged,” she says. “It was like having a great editor. He was more like a co-conceiver of it. He had a perfect ear if things got too sudsy or self pitying or analytical or too detailed.”

Ms. Allen is generous with praise for those who helped her along the journey through cancer, from her stepdaughter Kate Feiffer (who she describes as “an incredibly kind person”) and playhouse director M.J. Munafo to fellow actress Brooke Adams, who encouraged her to see the project through when self-doubt began to creep in. She feels a special affinity for the audience during the performance.

“The performing is exhilarating for me,” she says. “I love talking to an audience. It’s like your taking this trip together. They become this incredibly powerful presence.”

“This piece is like one huge personal essay,” she adds. “It’s like a dream come true. It’s a great, great feeling.”

I Got Sick Then I Got Better, also called The Big Boot, is a new solo performance written and performed by Jenny Allen, directed by James Lapine, for two nights only as the final Monday Night Special in the Vineyard Playhouse season.

Curtain will be at 7 p.m. on Sunday, August 24 and Monday, August 25. Reserved seating; all tickets are $25 and include a reception following the show. Partial proceeds will benefit the Martha’s Vineyard Cancer Support Group.