A really funny woman of a certain age: Meet Carole Montgomery

“You’re Too Old For That” is a regular series that explores inspiring activities being pursued by those over 50 years old who feel you’re never too old to do what lights you up.

The 93-year-old woman in the red leather jacket couldn’t stop laughing. Flanked by other women “of a certain age,” she was stunning and, like most of the other people in the theater, howling. On stage, Carole Montgomery, 68, was doing what she’d done since she was seven years old, when she first performed at a talent show in the Catskills. She was making everyone in the room laugh.

“Comedy is the big unifier. It really is,” Montgomery said.

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Montgomery’s comedy is fearless. She’s brash, loud and profane but she’s also kind and thoughtful. Physical on stage, Montgomery uses subtle but engaging facial expressions the way Harpo Marx (an early influence) did, and her delivery is almost musical, rehearsing the beats and rhythms of a joke until they land.

Montgomery was in Delray Beach to do a few shows. She still travels from her home in New York for work. She’s still a road dog, still grinding. The audience in Delray Beach may skew decades older than Montgomery, but that’s part of what she loves. She plays for everyone. A 75-year-old woman told her after one show, “I haven’t laughed this hard in such a long time.”

This philosophy drove Montgomery to create Funny Women of a Certain Age, a stand-up showcase that brought her national recognition at 60. The show spotlights older female comedians, most with decades of stand-up behind them. The show began in New York City clubs before Montgomery sold it to Showtime in 2019. The first special featured Fran Drescher (only her second televised stand-up), along with Luenell, Lynne Koplitz, Kerri Louise, and Vanessa Hollingshead. It became Showtime’s highest-rated comedy special ever. At the time, Montgomery didn’t have an agent and didn’t have a manager.

“Yeah, I was pretty proud of that one,” she said.

“It’s not often that someone sustains in show business for 47 years straight. And a woman, no less,” says Vicky Kuperman, a fellow comedian and close friend who met Montgomery in 2012 when they both volunteered for Hurricane Sandy relief. “Carole is a walking history book. Carole is a living legend.”

The setback becomes the setup

Montgomery never had a backup plan.

“All I knew was that I wanted to do this, and I was going to do it no matter what,” she said. “I didn’t realize it was going to take a good 45 years for me to have success.”

She was 21 and working in the tech department at a summer stock theater when a fellow crew member told her she was really funny and should do stand-up. Back then, she said, “nobody even knew what a comedian was.”

Nevertheless, she started performing at Pips in Brooklyn, a legendary now shuttered club, where David Brenner, Andrew Dice Clay, Joan Rivers and many other comedy legends once graced the stage. Growing up in Brooklyn, Montgomery carries the same chip-on-the-shoulder attitude that Brooklyn’s native kids are known for. But she also grew up in a home filled with stories and laughter. Her father bartended in the Catskills during the summers. He was funny and loud and told great stories, Montgomery says.

“He loved to crack up a room,” she remembers.

He introduced his daughter to the Marx Brothers and Abbott and Costello. Montgomery’s mother had Gracie Allen timing: quiet until she said something that floored everyone. Beyond her parents, Montgomery found inspiration in the greats. She saw Richard Pryor: Live in Concert at a theater in Times Square in the late 1970s.

“That movie changed my life,” she said. “This guy, he’s funny and fearless.” She also admired Lily Tomlin’s solo work and George Carlin.

For years, Montgomery waitressed and performed at comedy clubs at night. She recorded late-night talk show sets on VHS tapes, studied the comics, and analyzed their rhythms. She also sat in the back at clubs and watched. Fellow comedian Peter Spellos gave her a regular weekend spot at his club, Who’s on First, in Manhattan.

“I was just trying to become who I was going to become,” she says.

The industry, notorious for being tough on women, didn’t give her much of a break. Working and being a mom is hard in any industry. But for comics the road dog life made it impossible to be a presence at home. When her son turned four, Montgomery wanted a more convenient working life. She was touring a lot. And she would look back at her little boy before heading out and he would always fall out in tears when she left home.

“I wanted a job where I could do comedy but also stay home,” she said.

That’s when a residency in Vegas came calling. For ten years, Montgomery starred on the Vegas Strip, made a living and raised her son.

When she and her husband decided to move back to New York. The comedy scene had completely changed and she was told, “We don’t know you.”

The Internet changed everything …

So she started over. At 48.

Nonetheless, she says, had she stayed in Vegas, she never would have created Funny Women. This setback became a setup for her.

Carole Montgomery during her Vegas residency; photo courtesy of Montgomery

“That, (Funny Women) to me, is my legacy,” she said.

Fellow comedian and friend Kuperman watched Montgomery’s journey up close.

“What would most people do in their late 50s?” she says. “Carole re-assessed, re-invented, and tried again. This time, she chose something personal, something relatable, and something that would lift others up. She didn’t just succeed; she cemented a legacy.”

The ‘funny women bump’: a legacy takes shape

The idea for Funny Women came to Montgomery in 2015, after recording a podcast with female comics. They swapped war stories about the road and the industry’s misogyny, cracking each other up. Walking home, Montgomery called her husband.

“There should be a show with older female comics. We’re all really great. We just haven’t been offered the success that other comics are,” she said.

The show first premiered at a mini-comedy festival in Brooklyn with Janeane Garofalo and Judy Gold. The show landed a six-year residency at a club on the Lower East Side. It was noticed and a bidding war between cable networks broke out. Showtime won. Montgomery, then 59, chose the network because they’d given her her first big break in 1992, when “Comedy Club Network” named her one of the year’s top up-and-coming comics.

Montgomery calls what she’s built “the funny women bump,” a platform that helped launch Luenell to an HBO special and gave Fran Drescher space to prove her stand-up was legit. Since that first Showtime special in 2019, Montgomery produced two more: More Funny Women of a Certain Age in 2020, featuring Caroline Rhea, Carol Leifer, Tammy Pescatelli, Julia Scotti, and Thea Vidale. Then Even More Funny Women of a Certain Agein 2021, featuring Teri Hatcher, Wendy Liebman, Leighann Lord, Monique Marvez and Marsha Warfield.

“I really just wanted to get more eyeballs on older women,” she says. “When I look back at it now, I’m like, ‘oh shit. I did that.'”

“I’m 68 now,” she says. “My ambition is different.”

And comedy is no joke these days.

“Everyone is uneasy. Comedy becomes a life raft for people,” she says. “They just want to go away and not think about anything for an hour.”

Kuperman calls Montgomery her “3am friend” — the kind you can call with a shovel and no questions asked. “I hope Carole and I meet at diners from now until eternity,” she says. “Always separate checks, of course.”

Montgomery shows up. And when she does, women in red leather jackets laugh until they cry.