Jessie A. Gilbert spends her days handling legal matters involving estate planning, probate, family law and taxes in the Greenwich office of Cummings & Lockwood. She's known as a serious attorney and a subject matter expert who has authored several articles for legal publications.
She's also been known as a queen, an evil nurse and a ditzy nun, to name just a few of her alter egos. For the past 25 years, Gilbert has been participating in local theater throughout Fairfield County on a regular basis as a creative outlet for her artistic side.
"The fun thing is playing people who aren't like me," Gilbert said. That would include the character Jeri Neal from "The Dixie Swim Club," the flighty and eccentric nun Gilbert played in May for the theater group Curtain Call of Stamford.
"I'll do drama or comedy, but not musicals because I can't sing," she said. "Sometimes I'll see clients in the audience and I think, 'What was I just doing?'"
But her performances are always well-received by clients and other theater-goers, and Gilbert has enjoyed these volunteer roles for two decades. She was active in theater in high school and at Hamilton College during her undergraduate days. "I was thinking of making it a career, but then I realized I needed to eat so I went to law school [at Case Western Reserve University] instead," Gilbert said.
Living in Fairfield County where there are several local theaters, she got the itch to return to stage and auditioned and earned a spot in Neil Simon's "Rumors" after seeing a casting call in a local newspaper. Since then, Gilbert has averaged about two shows per year. She has been most active with Curtain Call, Town Players of New Canaan, and Westport Community Theatre.
"It's this hobby you can only do when someone else says you can do it," Gilbert said. Even though local theater is a group of volunteers, participants must go through intense auditions to earn their roles. They can't simply show up and receive a part.
Earning a role means approximately six weeks of rehearsals every night and weekends followed by three consecutive weekends of performances. "You have to say goodbye to your friends and family for a while," Gilbert noted. "I have to fit it in around my practice, and I don't have much personal time when I'm preparing for a show."
With her busy practice, she can't always audition for all the plays she's like to. So when she commits to auditioning for a certain role and doesn't get it, the rejection stings. "That's the toughest part, even in community theater," she said. "You get a call from the director [with bad news] and it feels like getting jilted."
Back in 2005, Gilbert had just experienced such a rejection when she received a separate call out of nowhere. A theater group was producing "The Lion in Winter" by James Goldman, which reveals the personal and political conflicts of Henry II of England, his wife Eleanor, their children and guests during Christmastime in the 12th century.
Apparently, the woman who was chosen to play Queen Eleanor was removed from the cast for failing to learn her lines, the only time Gilbert has heard of that happening in community theater.
"I was asked at the last minute to come into the leading role, and I had only three weeks to learn it" over the Christmas holiday, Gilbert recalled. "I couldn't say no because it was such a great part."
The experience was a rush after pouring so much emotion and time into her role, and then she felt the jarring reality that hits after a production concludes.
"You do this play and after the show people are standing and applauding you," she said. "Then you go back to work and you're dealing with a lawyer in an adversarial setting and you want to say, 'You can't talk to me like that. I'm Queen Eleanor!'"
Right now, Gilbert is between shows and eyeing some possible opportunities in September. She enjoys the diverse mix of people in community theater where the local wealthy resident plays a minor role next to the young local bookstore clerk who is the lead.
Some of Gilbert's other roles have been Nurse Ratched in "One Flew Over the Cuckoo's Nest" and various roles in "The Laramie Project," among just a few of her nearly 30 show credits.
"Everybody is in this for the love of theater and that's the great equalizer," she said. "When you're working with other people, you're only as good as the others on the stage. Community theater is very collegial, and the social aspect of it is really nice."•