On a recent Wednesday evening, Chris Fleming was dressed in a vintage tank top loaned to him by his girlfriend’s mother, waiting to feel the sting of his own mother’s purse on his cheek — all part of the insanity of “Gayle,” Fleming’s Web series featuring power-walking, ultra-competitive suburban housewife Gayle Waters-Waters and the family and friends she terrorizes on a regular basis. But this was rehearsal for “Gayle Live,” a theatrical adaptation of the series, which recently wrapped up its second season. This weekend’s two-night run at the Davis Square Theatre is the next step in a family affair that has captured the attention of comedian Margaret Cho and a dedicated following.
When Fleming, 26, a former Boston comic, first thought of adapting his stand-up character Gayle for video, he knew he wanted to balance her hyper-absurdity with a realistic setting and cast of characters. He began by casting his mother, Nancy, as neighbor and couscous-loving rival Bonnie. “She’s funny,” Fleming says. “I imagine [the show] happening in Stow, in my town where I grew up.” In fact, Gayle’s house, in the series, is shot partly at his parents’ house in Stow and partly in the apartment he and his girlfriend, Melissa Strype, share in Los Angeles.
Some parents might be hesitant to step in front of the camera, let alone to be cast opposite their son in drag. “Well, you know what, then I feel bad for them if they would say no to something like this,” Nancy Fleming says. “You see your adult child in a different way.” She says she and her husband, Joe, have encouraged Chris since he started signing his kindergarten papers as “Chris the Comedian.” And she says she’s not afraid of being part of a live show, even though she has no professional experience. “It’s just such good fun,” she says. “And it’s so silly.”
The rest of the cast is filled mostly with Fleming’s family and friends. “I think working with everyday people is the funniest,” he says. “You have the best results, at least for this.”
Strype directs and co-writes the episodes and plays Gayle’s daughter, Terry Gross Waters-Waters. Bruce Burgwinkle, father of a childhood friend, plays himself, and becomes a sex object for Gayle and the neighborhood women to lust over. The one professional in the regular cast is local comedian and actress Jessie Baade, who plays Gayle’s not-so-bright friend Linda. Gayle’s suffering husband, Dave, is an uncredited pair of legs in khaki pants.
Fleming and Strype travel back to Boston from LA to film sequences with the Boston-based crew in and around Stow. They have to work quickly, which helps create some of the informal feeling of the series. “We give them a couple of lines,” says Strype, “and they’ll be doing their daily tasks somewhere else in the house, and we just say can you come here real quick, stand there, we’ll film these.”
Gayle Waters-Waters has evolved considerably from her first incarnation in Fleming’s stand-up. He realized Gayle had to be softened from the woman who would dislocate her shoulder to take all her groceries into the house in one trip and hide in the hall closet to menace Dave for choosing the wrong fleece pullover. And in the last few episodes, she has warmed up a bit, even fighting an enormous egret to help Dave save face in a bird-watching competition. “There’s more vulnerability,” Fleming says. “You can’t just keep going through that same door, snorting Kashi jokes. She needs to become a real person, and she’s basically an extension of me now.”
‘There’s more vulnerability [to Gayle, above]. You can’t just keep going through that same door, snorting Kashi jokes. She needs to become a real person, and she’s basically an extension of me now.’
“Gayle” has been winning fans and recognition steadily since it debuted in April of last year. Fleming gained high-profile support in February when comedian Margaret Cho found the series. “I was on tour at the time, and my touring group and I, we just started watching obsessively and tweeting at him,” she says. Cho calls Gayle “one of the best characters of all time,” and appeared in the April 7 season 2 finale as Yo-Yo Ma. “Everybody I’ve introduced it to goes really crazy for it and thinks it’s just genius,” Cho says.
Fleming says he is sometimes recognized as Gayle when he’s out in public. Baade was recognized as Linda in March by a group of high school students in Oswego, N.Y. “These kids memorize it,” she says. “They recognized me because they watch it again and again and again.” In August, Nancy found a bunch of strange kids screaming on her front doorstep and thought they might have been her son’s friends. “Then I realize that they’re screaming ‘Bonnie!’ ” she says. They turned out to be six recent high school graduates who had come on a pilgrimage from Connecticut to find the home of Gayle.
Now, while Fleming and Strype contemplate funding for a third season of the show, they have decided to take it on the road. They originally planned two shows at the Davis Square Theatre, but when those sold out quickly, they added a third, which also sold out. They then added a late Friday show for which some tickets were available this week. Fleming says they are now pondering doing a version of the show on a Midwestern tour.
At Davis Square, he is looking forward to seeing more of the actual faces tied to the online “likes” and stats. “When you load these things on YouTube, it’s kind of a quiet, lonely process,” Fleming says. “I’ll sleep easier at night actually being able to see living, breathing people enjoying Gayle Waters-Waters.”