Jo Firestone Channeled Her Inner Old Lady to Teach Comedy to Seniors

In February 2020, about three weeks before New York City locked down, Jo Firestone decided to start teaching stand-up comedy to senior citizens. What at first seemed like terrible timing ended up being a blessing in disguise. Now, Firestone and her elderly students are the subject of the new documentary special Good Timing, which premieres Friday, Oct. 15 on Peacock.

“I had some downtime,” the 33-year-old stand-up comedian and former Tonight Show writer explains when I ask how her career took this unexpected turn. “I was not working at the time and I didn’t see any career opportunities in the future. And so I was like, ‘Well, I might as well spend my time doing something instead of sitting around.’” Comparing herself to a squirrel who tries to save enough food for winter, she says that despite recurring roles on critically acclaimed series like Shrill, “I was worried there were no more acorns.”

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The prospect of making a special with her elderly students was a lot more appealing than trying to write and perform her own hour of stand-up during a time when getting on stage was becoming increasingly difficult. “If you were like, ‘Go write a special alone and come back in three months and it should be good and you haven’t bounced it off of anyone,’ I’d be like, this is going to be really bad,” she says.

Instead, she offered up her services teaching a comedy workshop at the Greenwich House Senior Center. “So now I’m technically an employee of New York City—I think it’s called the Department of the Aging?” she says. “When I originally signed up to do this, it was a 13-week commitment and now it’s been like two years and there’s no sign of it stopping.”

The class quickly moved onto Zoom, meeting every Monday morning at 10 a.m. without exception. When Firestone realized she might be able to turn their lessons into a special, which culminates in a 2 p.m. performance for friends and family, they gathered in person once again. It was during “that six-week window where it felt safe,” she says—basically between the first vaccine wave and Delta—and everyone agreed to go maskless except for one 76-year-old woman who wore three masks taped to her face.

“I’ve always really enjoyed how a lot of senior citizens are less self-conscious than people my age or younger,” Firestone says of her free-wheeling students, who are not shy about using the most intimate details of their lives as material. She didn’t quite realize how “nasty and raunchy” their jokes would be. “Some of them don’t even curse, but they’ll talk about getting an erection,” she says.

The documentary special is full of both intentional and unintentional humor in ways Firestone never could have predicted. She recalls one moment when she and the class were riding a party bus to their big show and she urged them to “pump each other up.” One 88-year-old student started singing “John Jacob Jingleheimer Schmidt” at the top of her lungs and everyone else joined in. “I never would’ve thought of that. I never would have told anyone to do that,” Firestone says. “And that’s the most beautiful thing that we could’ve ever hoped for.”

When we meet each of the students in the special, only one declines to share her age. Tequila Minsky is a “New York famous” photojournalist who currently has blue highlights in her dyed black hair—more punk rock than old lady. Her material includes a rant about whether it’s more efficient to kill the cockroaches in her apartment with a sponge or her hand. She now imagines the “horror” of getting Combat traps as fan mail from viewers who watch the special.

After taking the class, Minsky says she has a lot more “respect” for comedians who can do a whole set of funny jokes. She plans to keep trying to make people laugh for the rest of her life, but doesn’t see comedy as a second career. “You know how when you’re a kid or you have a regular job and Monday’s coming and you don’t really want it coming because it’s Monday?” she tells me. “This is not how it is having this class on Monday morning. You laugh for 45 minutes! Just imagine, you start your week by laughing for 45 minutes. Then it’s downhill from there.”

Minsky previously appeared in Firestone’s 2020 Adult Swim special Rate the Cookie, which, like Good Timing, was directed by former Nightly Show field producer Julie Miller. For Rate the Cookie, Firestone stationed herself outside of a grocery store in the middle of winter and handed out free cookies before offering strangers a choice between $50 cash and her real phone number so they could become friends.

“I guess I did want more people to take the friendship,” Firestone admits now. “I guess if I had the choice, I would’ve kept my money and gained friends.”

Firestone grew up in St. Louis not realizing that “comedy could be a job,” an outlook she blames partly on the fact that her family didn’t have cable TV. “There was definitely some genetic sadness,” she says of her early years. Whenever she did get a chance to watch comedy, she would laugh and feel OK. At first, that was her only real goal, to feel “better for the moment.” But once she did start trying to make people laugh professionally, her ambitions were always much larger than what reality allowed.

“I was really just so ambitious about what I wanted to do and had no way to execute that,” she continues, recalling the time she wanted to put on a big Christmas spectacular show featuring dozens of Liza Minnelli impersonators. Firestone tried to find a company that would sponsor the show and the only bite she got was from an obscure potato chip company. “And the way they sponsored me was they gave me 14 boxes of expired potato chips,” she recalls. “I had so many expired chips and I had spent way more money than I had. And nobody came to the show.”

Asked to describe what her comedy was like at the beginning, Firestone offers up five adjectives: “Sloppy, chaotic, under-prepared, undercooked, raw.” But if there’s one word that’s used most often to describe Firestone’s brand of humor it’s “awkward.”

“I think a lot of those words like ‘awkward,’ ‘quirky,’ it is what it is,” she says with a sigh. “You don’t want to call someone a loser or something so you’re like, ‘They’re awkward!’ But I’m not trying to be awkward. I’m trying to be socially normal and smooth, but it comes out in a different way.”

Instead of a “big break,” Firestone says her comedy career has been more a “soft landing” that began when she was hired as a writer on The Tonight Show just after the 2016 election. “They told me right before I got on an airplane going home for Thanksgiving and the airplane was pretty good,” she recalls. “And then I was like, ‘Oh no, this is a mistake.’”

Firestone was not eager to enter the late-night TV scene at “that really weird time” when all anyone was talking about was the newly elected Donald Trump. But she ended up getting thrust into that world, even playing characters on screen like Melania Trump’s body double, Kellyanne Conway, and most memorably, Education Secretary Betsy DeVos.

“One day, they were just like, ‘You’re going to do Betsy DeVos,” she says. “And I was like, ‘What? I don’t even have an impression!’ And they’re like, ‘You’ll figure it out.’” Firestone remembers being rushed into hair and makeup before she’d really had a chance to think about what she was going to do, but when she got in front of the audience, instincts kicked in and she made them laugh. “It was definitely nerve-wracking,” she says. “It felt like a chicken, no-head kind of thing.”

The show business job that has been more her speed over the past few years has been on the beloved Adult Swim project Joe Pera Talks With You. Firestone and the show’s mysterious creator and star Joe Pera first connected after they both performed stand-up at the same show in New York and the audience didn’t like either one of them. “That was a nice bonding moment,” she says.

Joe Pera Talks With You, which is set to return for its third season next month, could certainly be described as “awkward” or “quirky” but it is so much more than that. With his uniquely calm and deliberate musings about life in the upper Midwest, Pera has created a viewing experience that is almost meditative. The laughs come more at disbelief that he was able to get the show on television at all.

As for her co-star, who never seems to break character even when appearing “as himself” on The Late Show with Stephen Colbert or elsewhere, Firestone is a bit evasive when describing what he’s “really” like behind the scenes.

“I would say there are differences, for sure,” she says, citing the fact that he’s not actually a choir teacher and does own a credit card. “But I think it’s probably a fair representation. I don’t think it’s that far from who he is.”

In addition to writing and producing the show, Firestone plays the title character’s love interest Sarah, whom Pera describes in one episode as “like an old woman was made into a young woman, in the best possible way.”

When she first came to that line in the script her initial reaction was, “Huh?” Then she admitted, “I guess I see it.”

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