Humor and tenacity pay off for 'woman-of-a-certain-age' standup comic Carole Montgomery

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SOUTH EGREMONT — On Tuesday, Netflix released Amy Schumer's latest standup special, "Amy Schumer Growing." The 37-year-old actress, author and comedian has undoubtedly influenced many up-and-coming female comics with her raunchy humor; her casual, courageous feminism; and her substantial fame, a triumph in a comedy sphere historically dominated by men.

But a group of veteran female comedians will also be making statements in the stream scene this week, perhaps inspiring older generations of comics in turn. Premiering at 9 p.m. Saturday on Showtime, "Funny Women of a Certain Age" features Fran Drescher, Luenell, Vanessa Hollingshead, Lynne Koplitz, Kerri Louise and Carole Montgomery delivering 10-minute standup sets interspersed with stories about the difficulties women face in the comedy business. The night before, Montgomery will bring the stage show that spawned the TV special to The Barn at The Egremont Village Inn. Joined by one of her series' regulars, Leighann Lord, and Jenny Rubin, Montgomery promises a night of standup comedy that will contain different material than the special and will appeal to members of both sexes.

"I think people get afraid when they hear 'all-female show.' They're like, 'Oh, they're going to talk about hating men ... and it's not like that. It's that funny, smart humor," Montgomery told The Eagle during a telephone interview.

The TV special won't shy away from the sexism Montgomery and other women have had to face as female comedians, though. Montgomery provided an example of prejudice she encountered early on in her career, when she was a headlining comic traveling about 40 weeks per year. One day, her manager informed her that a show six months later had to be canceled. The venue had just hosted a female comedian.

"I just remember that the club owner called my manager and said, 'She bombed, so I'm canceling all the women on the calendar,'" Montgomery recalled. "I lost work because some other woman didn't do well, so he just assumed that all women must suck."

A lack of all-female comedy lineups motivated Montgomery to create "Funny Women of a Certain Age." The idea for the show emerged after a podcast appearance with three other older female comedians.

"We just had the best time, and I thought to myself, 'You know, we never get to hang out and do stuff like that,' because they only, always, put one woman on a show," the 60-year-old Montgomery said.

The comic resolved to bring her funny female friends together onstage. She initially made a list of more than 100 female comedians over 50 who were consistently working, if not well-recognized. Then, she lowered that age to 40, adding about 150 more names. Originally called "Women of a Certain Age Comedy," the show debuted in 2017, touting a rotating cast of female comedians who weren't afraid to touch on subjects that were normally considered taboo for, uh, women of a certain age. A monthly residency at the Kraine Theater in Manhattan helped boost the series' profile. Soon, the show had TV suitors. Montgomery ultimately went with Showtime because the channel had given the comedian her first big break: a special just a few months after her son's birth 27 years ago.

"I'm very big about loyalty," said Montgomery, who has appeared on "The Oprah Winfrey Show" and "Politically Incorrect" with Bill Maher, among others.

The forthcoming Showtime program was filmed in Brooklyn, where Montgomery grew up. During her youth, she watched "I Love Lucy" with her family at dinner. Lucille Ball's pioneering work in the sitcom ingrained in Montgomery the belief that she could be considered funny.

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"If Lucy could do it, I could do it," Montgomery recalled thinking.

She compares Drescher, "The Nanny" star whom Montgomery landed to headline the special, to Ball.

"She's an icon. In fact, I say that in the special. She's my generation's Lucy," Montgomery said.

In her own act, Montgomery strives to mirror Richard Pryor's honesty. Early on in her career, that meant talking about life as a single woman in New York City, trying to find a boyfriend. Later on, her marriage and child came into play.

"I married a musician, ladies, how great is that?" Montgomery said during a set several years ago. "Yeah, and my son's a musician, too. So, you know what that means? I'll be working the rest of my f------ life, that's what that means."

Now, Montgomery is talking about aging, about wanting to be a grandmother. Her jokes come from her head, a different approach than Lord's.

"I always laugh at her because she's such a brilliant writer. She actually has handwritten notebooks of all of her jokes, which blows me away. You can say to her, 'I want you to do a bit about cats and then going to the hospital and then running.' She'll go, 'Hold on. Let me figure it out.' And she'll have jokes," Montgomery said.

Montgomery is excited to be performing with Rubin. The Barn proprietor/manager typically produces the South Egremont venue's comedy nights, which often include female performers with impressive resumes. Montgomery's own decades-long run in comedy stems from both her humor and tenacity.

"When people tell me I can't do something, it riles me up," she said. "That's what gives me the power to keep going because my entire career's been: 'Oh, you're a woman. You shouldn't talk that way.' Or, 'You're married. You shouldn't talk that way.' Or, 'You're a mom. You shouldn't talk that way.' And, every time somebody told me I couldn't do something, I was like, 'OK, now watch.'"

Benjamin Cassidy can be reached at bcassidy@berkshireeagle.com, at @bybencassidy on Twitter and 413-496-6251.


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