Carole Montgomery is a funny woman of a certain age, which is why her new Showtime stand-up showcase is so important to her. At age 47, comedian Montgomery moved back home to New York City in 2006 with high hopes of a third act for her stand-up career. She had almost three decades of experience under her belt. From the smoky Brooklyn rooms of the early 1980s with Andrew Dice Clay to years of working the road, she climbed the ranks during comedy’s big boom.
Coming off an enviable decade-long stint in Las Vegas, Montgomery’s plans were slowed down by a world she barely recognized. The profitable heyday was no more.
In its place were bringer shows, YouTube stars, and an industry that favored youth. Those sweet, lucrative gigs were a thing of the past. For the next decade, she searched for her place and tried to stay relevant in this new, oversaturated market.
Carole talked to Laughspin’s Vicky Kuperman about how she overcame ageism and sexism to come out on top. Her brainchild, Funny Women of a Certain Age, premieres Saturday, March 23. It will be the first time six female comedians over 50 performed on a TV stand-up special together. The taping, done in January at The Bell House in the comedian’s native Brooklyn, represented a personal victory for a woman who simply refused to give up. When Montgomery, at the age of 60, stepped on stage to the sound of thunderous applause of a sold-out house, in the borough where she was born and raised, she did more than just come home. She arrived.
We had lunch at this diner almost exactly two years ago, almost exactly to the date, before you even thought of this idea.
Probably. And we were both talking about how we were not ever going to be doing stand-up because we both hated it so much.
What would you have told someone then about stand-up versus now?
I’d still tell them not to be a comedian. I’d still tell them not to. A lot of people have asked me why I brought it to Showtime—because there was a lot of interest in the show. Showtime gave me my break 27 years ago. So if you stay, and you work really hard, maybe you’ll get another break in 27 years from the first time you got one.
And what did it mean for you to shoot the special at The Bell House?
I wanted to go back to Brooklyn because I wanted to honor my parents. I wanted to go back to Brooklyn because that’s where I’m from. I was born in King’s Highway Hospital—or Coney Island Hospital. It was really important. Even though The Bell House isn’t where I grew up, I know that my parents would have been very proud that I brought it back there.
What is Funny Women of a Certain Age?
It’s a show about funny women who happen to be over the age of 50. Some of them you’ll know, you will have heard their name. But it’s also about women you’ve never heard of. Because there’s so many women in this business who are these great comics who work cruise ships, corporate gigs. They do theaters, who, nobody knows who they are because for whatever reason they never got a TV special or TV spot. When I came up with the idea I originally wanted it to just be 50 and over, and I had about 100 women. Then I decided, I have friends in their 40s, and I said, you know, I want to open it up to my friends. Once I opened it up to over 40, it became 250 people. There’s a lot of women. There’s a lot of content for a series.
There is. Do you think that women over 40, 50, 60 have way funnier things to say about their life experience and pain?
Oh, absolutely. But that’s what comedy’s about anyway. Comedy’s always about pain. It’s always about your experience. Richard Pryor—his first concert film where he talks about his heart attack, and he acts out his heart attack, is some of the most funny, brutal comedy you’re ever going to see. That’s what comedy is. You have to live your life. Not that young comics aren’t funny. There’s a lot of young comics who are funny. And it’s not just women—men, too—there’s something about living a life. I remember when I got passed at Catch A Rising Star, and I had just met my husband, who was my boyfriend. I’d do my late night spot and I’d run home to be with my boyfriend. And all the guys were like, “You know, you gotta hang out, you gotta hang out.” I thought, you know what, I want to live a life so I actually have something to talk about.
Speaking of living a life, you’ve lived a lifetime in comedy. 40 years now you’ve been hitting the stage?
Yes, I have. 40 years. I didn’t know what a comedian was then. The only person I knew was Johnny Carson. Sometime in the Fall of ‘79, I started going to Pips in Sheepshead Bay in Brooklyn. Joan Rivers used to go there, and David Brenner. I started with Richard Jeni and Andrew Silverstein—who became Andrew Dice Clay. But he started as Andrew Silverstein. Andrew Silverstein is one of the best impressionists you’ll ever see. His Jerry Lewis—he does an amazing Jerry Lewis. He was doing a take-off on Fonzi, and he became Dice. And Richard Jeni was one of the worst comics I’d ever seen. He was horrible, just horrible. Years later I walk into Catch A Rising Star, and I was one of the new comics there, and I heard someone killing in the room. I peak in and it was Richard Jeni. Which is something I always talk about: stage time, stage time, stage time. He was determined to be good because he knew he was shitty.
Your career over 40 years has an interesting trajectory with twists and turns. You became a club comic and then moved to Los Angeles. It seems like, for even women back in the day, you could live off this. Did being a woman really hinder you back then?
You were one of how many?
Maybe 10, maybe 15. They had audition nights. You would wait on line. I would sit there since 8:00 a.m. at Catch A Rising Star and wait until they gave you a number. I was on line with Margaret Smith, Rita Rudner. We would sit there and wait all day to get our ticket to go on stage.
So then you started working the road all over the country. You worked every week?
I was working at least two or three weeks per month. Good money. The going rate for headlining a Tuesday-Saturday was anywhere from $1,750 to $2,000 to $2,500—plus airfare, plus hotel. None of this, “We’ll give you $500 and you have to turn off the lights when you’re done.” You made good money.
And then Las Vegas happened.
This is the only time that The Secret has ever worked for me. I had been on the road and Layne (my son) was three- or four-years-old. Every time I had to go, I would wake him up to kiss him goodbye and he’d cry, “Mommy don’t leave me. Don’t leave me.” I’d go to The Riviera in Vegas, at the comedy club. I’d carry pictures and whatever hotel I was working, I’d make it like my home, with pictures of my family. And whatever hotel I was working, I was putting away my shit and said, “I would love a gig where I could be home and didn’t have to worry about leaving.” And the next fucking day I get a phone call, “Hey listen, the girl in the burlesque show, she had a heart attack and they need a replacement. I told her you would do it.” That week I did 27 shows. This was Crazy Girls. They would do their first dance number. I’d come in and say, “Hey everyone. Welcome to Crazy Girls,” and I’d do a couple of jokes. Then midway, I’d do a 10-minute spot. And that’s it.
And on this 10-minute spot, you were able to buy a house and support a family?
Yes. That happened. They offered me the gig. The girl was recuperating and they said, “Will you stay for the summer?” I said, “Absolutely, but my son has to live with me.” So I lived in The Riviera for two months. At the end of the summer, they decided they wanted me to stay on. They gave me a three-year contract. That turned into five years at Crazy Girls. Our son was about to go to junior high. We did not end well, and they didn’t want to pay me my contract. They wanted me to leave. I ended up leaving. I said let’s stay until June when he graduates elementary school. Somewhere in those few months, I got offered Midnight Fantasy. I said, if we stay, we’re staying for three years. I wanted him to have his friends. Once I took that contract, we were going to stay until the end of middle school.
Did you ever miss doing long headlining sets?
No. They were paying me a lot of money for 10 minutes. I would probably still be there working those shows if I didn’t have Layne. The money was great for doing 10 minutes.
When you moved back to New York, what kind of industry did you come back to? How did it change?
13 years ago, I came back to New York. So I was 47. I was shocked at the fact that there was still only one woman on a show. It was the same. How did we not move forward? I was shocked. I had had a feeling. I was putting out feelers. All the clubs I ever did were either closed or taken over. I remember going back to the Pittsburgh Funny Bone, which is no longer there. I used to make $2,000. By the time I came back, it was a $1,000. It’s the only industry I’ve ever seen where you don’t get a raise.
What do you think of bringers?
I think they’re horrible. Horrible. Nobody makes money except the people running the bringer shows. You’re taking advantage of young people. [Producers] say, “I’m doing a service.” The service is, you’re servicing yourself and you’re making money. Go to bar shows. Go to open mics. Make your own stuff. If you sit around waiting for the phone to ring—this business is brutal. I remember when I did the Oprah Winfrey show, Layne was three-years-old. So this was the biggest thing that had ever happened to me since Showtime All-Stars. I’m at the gym and all of a sudden, there’s me and Oprah ‘coming up tomorrow.’ Next day, I watch it. It’s great. I go over to the phone, pick it up, look at my husband, and I said, “It’s still working.” That was ‘95. She was at the height of her career. Didn’t change a thing for me.
You’re a producer now. How did you come up with Funny Women of a Certain Age? This was two years ago, right? Summer of 2017?
I was doing a podcast with three other female comics who are older. It was so fun. And I thought: I want to do a show with my friends. I started thinking of everybody I knew. I thought, Oh my god, there are so many great women and we never get to be with each other. When we did the interviews and interstitials with the women for the Showtime special, we’re all asked, “How many times are you the only woman on the show?” Everyone answers, “Always. I’m always the only woman on the show.” And there’s a different dynamic when women work together. If you play it right, the way I did, it’s a feeling of love and support. There’s no bullshit backstage at all. 10 minutes before I’m supposed to go on, I look in the mirror and say, “I really don’t like my hair.” Vanessa [Hollingshead] and Kerri [Louise], out of nowhere, started hairspraying me. A guy wouldn’t do that. They wanted me to do well. We had a monitor in the back. Everyone was watching each other’s sets. Everyone was happy that everyone else was doing well.
The media makes it seem like women are always against each other—and we are competitive. This business is competitive to begin with. It has nothing to do with being a woman. It has to do with being a comic. Every comic, whether a guy or girl, will be at an open mic at the beginning of their career, will see someone and go, “I’m better than that.” That’s how comics think. It has nothing to do with being a woman. I’ve always wanted to help someone else. Why wouldn’t I?
How did this go from an idea to a Showtime special in a year-and-a-half?
We premiered at The Cinder Block Comedy Festival. The Kraine Theater offered me a residency. We did a show in December 2017. My production partner, Dave Goldberg, came to see it and said, “This is a show.” We did a showcase for TV producers in February 2018. Amazon, Hulu, Netflix, Showtime, TruTV. Everyone was there. We did the show. It was an amazing show. Veronica Mosey, Leighann Lord, and Vanessa Hollingshead. She destroyed. I didn’t tell the girls the industry was there. Everyone was interested. We went with Showtime because of my history with them.
We did a road gig together once, and you gave me some great advice about what not to do in a comedy condo.
When Vicky and I were in a comedy condo—and by the way, it was one of the best comedy condos I’ve ever been in—
So you open the fridge in a comedy condo. You open up the fridge door. They have the row of condiments. Three or four jars of ketchup, three or four jars of mustard, and three or four jars of mayonnaise. You are not to eat the mayonnaise.
Because comics put their dicks in it.
Funny Women of a Certain Age, starring Carole Montgomery, Fran Drescher, Luenell, Lynne Koplitz, Kerrie Louise, and Vanessa Hollingshead, premieres on Showtime this Saturday, March 23rd at 9:00 p.m. ET/PT.