Comedian Chris Fleming is a human hyperbole machine. “Every Cambridge vegan is polyamorous,” he says with casual authority, leaning over a booth at Veggie Galaxy as we meet up for lunch in Central Square a few weeks ago.
It’s the kind of nonsense that Fleming has become famous for spewing in Gayle, his YouTube series about the white upper-class trials and tribulations of mother, wife, and overly competitive neighbor Gayle Waters-Waters. Other quirky analogies organically work their way into our chat; he drops “shaking like a Chihuahua at a parade” and “struggling like a spider crawling up a toilet bowl” in his steam-of-consciousness conversation. Glancing through his four years of YouTube videos, there isn’t a single car rant or episode of Gayle that escapes his detailed nonsense.
“I guess it’s just how I write — I think if you have enough time on your hands you can come up with anything,” he says of his super-detailed brand of comedy. His long red locks, the other part of his signature look, stay in place with a “sea salt spray” from Amazon Prime he has handy in his coat pocket (“Just puff it up so you’ve got the full-on show pony tower right here,” he says, demonstrating in the middle of the restaurant). Paired together, his quips and ‘do create the essence of Gayle Waters-Waters, his ginger and overt female alter-ego.
But Mrs. Waters-Waters hasn’t seen any new adventures in suburbia in more than a year. Fleming has shifted towards focusing on stand-up — at least for now — stopping in his native Massachusetts to perform at The Wilbur on Thursday (March 9). And while there won’t be any sort of Gayle Live components that some of his previous live performances have had, it’s hard to push Gayle, the series and the character, out of anyone’s consciousness when she is the most accurate satire of Massachusetts living to date.
Comedians who imitate Boston culture usually tend towards cheap shots at Southie accents, the Red Sox, and Dunkin’ Donuts (ahem, Casey Affleck), but Fleming represents Massachusetts through Gayle in the authentic way that only someone who’s lived here their whole life can. And of course, with the exception of his last few years spent in Los Angeles, Fleming has spent the majority of his days in the Bay State.
Fleming grew up in Stow and didn’t move out of Massachusetts until he was 18 when he attended Skidmore College in Saratoga Springs. While working on Gayle, he would return home to Massachusetts to film every episode.
“That is kind of my love song to Massachusetts,” he says of his YouTube series. Cue Gayle’s dilemmas of navigating Trader Joes and keeping up with the neighbors in the “new d” (Gayle’s slang for new housing development).
“I love central Massachusetts so much; the fear, the excitement, the tension, the anxiety, I just love it,” Fleming says. “Did you ever see The Witch? That is the best representation of growing up in Massachusetts I have ever seen. Just the cold November woods, and you don’t know what’s in those woods… and the fear of the devil. And Matchbox 20 playing around the clock with a little Dave Matthews sprinkled in.”
The fact that Massachusetts carries its initial conservative roots with it remains an endless source of inspiration for the comedian.
“Massachusetts is progressive in a way that you’re not going to go to a party and still have ‘Call Me Maybe’ on the playlist,” he adds. “We don’t really allot ourselves that much time for happiness. It’s Puritan.”
He details his formative years in Massachusetts while munching on a grilled cheese sandwich just one T stop away from where Gayle Waters-Waters was conceived in Harvard Square. Between the ages of 17 and 22, Fleming would hit up The Comedy Studio, owned by Rick Jenkins, to flesh out his standup skills.
“It’s this place that kind of encourages experimental comedy,” Fleming says. “The impetus is more on authentic voice than it is on — [creepy voice] ey, are we dating? — the traditional shitty club humor. The crowds were always willing to get wacky and go with you on bizarre shit. That’s where I started developing the character Gayle in my standup there — those 10 minute chunks. It’s just an amazing training ground.”
During his quasi-break from Gayle, Fleming has delved into making some “bullshit music,” like his profession “I’m Afraid To Talk To Men”, and even touched upon the comedic taboo subject of politics. But for Fleming, his impersonations of people in the political arena usually boil down to the art of imitation he learned in theater school.
“Those for me are just character studies,” he quips. “I like the way Gary Johnson talks. I was like ‘Who is this sexual deviant?’ I just like that he was clearly a deviant. People were like ‘Oh you should have mentioned Aleppo.’ I don’t care about the Aleppo thing, I just figured that his vibe was one of a guy who was going to invite you to a threesome at a Kia dealership. And Betsy DeVos, same thing, it’s comical to me because that whole video was just so clear that she was so sinisterly wealthy and the fact that she has no business doing that job, but it’s always more for me about the character.”
He proceeds to mime his Gary Johnson “I’m a mess” line and head-tilt flawlessly.
Since those fateful days developing Gayle on Massachusetts Avenue, Fleming has been able to quit his job as a SAT tutor and focus solely on his comedy for the past four years. “With these new tours and everything, the little videos I make, I’m kind of experimenting,” he says. “Gayle took everything out of me and my loved ones. My girlfriend, my family — everyone was just dripping with sweat. If I were to do something else, obviously I would need a crew, it would need to be legit. I couldn’t make something like that again without the proper backing.”
While he marinates on what kind of character his YouTube series will focus on next, his North American tour, dubbed “SHOWPIG”, boasts Fleming’s lesser-known area of study in college: Dance.
“There’s a big modern dance aspect in this new show where we just kind of Kate Bush dance, inspired by this time my dad accidentally told my soccer coach he loved him on the phone. It’s about the ‘Dante’s Inferno’ he then inhabited, and there’s this very erotic Kate Bush modern dance that goes along with it,” he says. “I’ll be talking about the polyamorous community — I have a song about that — I’ll be talking about how I think the height of privilege is thinking people care what you thought about La La Land. I’m more confident for this particular show than I have been for any of the Gayle shows.”
His most recent Massachusetts gig was to a sold-out crowd at The Regent Theater in Arlington last August. Ironically, he’s never been to The Wilbur, the theater he’s close to selling out (“I’ve seen courtroom sketches of it,” he says). Filling the theater is an exciting next step for Fleming, who skyrocketed his career by nailing his punch lines in front of a camera — not a live audience. And while YouTube is how most people were introduced to his off-brand comedy, performing live still a highlight for the Stow escapee.
“It’s lonely. You don’t hear the laughs when you’re doing it by yourself and you’re focusing the camera on your bichon who’s sitting on a chair,” he says. “There’s nothing like live performances for me. I love it.”