'Lady Randy' onstage at Shakespeare & Company

It was Goldie Hawn who so succinctly summed up the three options for actresses: They can play a babe, a district attorney or "Driving Miss Daisy." Local theater artist Anne Undeland was not happy facing those last two archetypes.

"I'm an actress over 50 and I got so depressed by the relative dearth of good roles for women my age," says Undeland. "In the theatrical canon, we play mothers and grandmothers. Women my age are not allowed to have the full spectrum of romance and tragedy and adventure and sex and motherhood. I decided that I could keep complaining or do something about it."

Undeland picked up her pen and became a playwright. Her first full-length work is "Lady Randy," a portrait of Winston Churchill's mother, who was known for much of her life as Lady Randolph. Undeland performs the lead in WAM Theatre's world premiere production, which opens Saturday and runs through May 5 at Shakespeare & Company in Lenox, Mass.

"Researching her life, I thought my god, you can't make this stuff up," says Undeland. "I fell headlong in love with this woman, who's deeply flawed and vauntingly ambitious."

Born in Brooklyn and raised in New York and Paris, the former Jennie Jerome was a talented pianist and prolific playwright who had works performed on London's West End. At age 20, she married Lord Randolph Churchill, son of the seventh Duke of Marlborough. The couple had two sons; the first, Winston, was born in 1874 just eight months after their marriage. After Lord Randolph died in 1895 at age 45, she went on to marry twice more, both times to men more than 20 years her junior.

It's the marriages and love affairs that have dominated the historical picture of Lady Randolph.

"Historians refer to her as loose or a harlot. Had she been a man, this behavior would have been admirable or not remarked on at all," says...