Her third “Funny Women of a Certain Age” comedy showcase premiered Nov. 24, 2021, on Showtime
Above: Carole Montgomery (left), with Luenell, Lynne Koplitz, Fran Drescher, Vanessa Hollingshead and Kerri Louise in 2019 at the first taping of Funny Women of a Certain Age at The Bell House in Brooklyn, NY.
The first time Carole Montgomery reached out to me, it wasn’t even about her or one of her showcases, but rather about trying to promote one of her peers. Back in 2014, Montgomery wanted me to know about Rhonda Shear and her attempts to revive Up All Night, the old late-night staple Shear had hosted on TV for USA in the early 1990s. Montgomery didn’t work on Up All Night then or way back then. It wasn’t even one of her many TV credits from the 1980s comedy boom. She just helped Shear because it’s in her nature to nurture. Perhaps why she branded herself as “National Mom.”
Here are some clips of Montgomery performing on shows during the 2000s, including Comics Unleashed, Nick at Nite’s Search for the Funniest Mom in America, and Politically Incorrect with Bill Maher.
Her second Showtime showcase, More Funny Women of a Certain Age, premiered on Showtime on March 14, 2020, featuring Caroline Rhea, Carol Leifer, Tammy Pescatelli, Thea Vidale, Montgomery and Julia Scotti.
Last night, the third showcase premiered on Showtime. Even More Funny Women of a Certain Age is fronted by actress Teri Hatcher, along with Montgomery, Wendy Liebman, Monique Marvez, Leighann Lord and Marsha Warfield.
You can listen to my podcast with Montgomery here:
Here is an edited and slightly condensed transcript of my conversation with Carole Montgomery!
Sean L. McCarthy: Congratulations on not your first not your second but your third Showtime special, Even More Funny Women of a Certain Age, and I guess now we’ve finally determined what that certain age is.
Carole Montgomery: Have we really?
Spoiler alert. You do, in the opening to the third special, say the certain age is 50.
Yes, it’s always started as women, female comics over the age of 50. But you know, it’s interesting, because when I was first doing this back in the day when it was just a live show. I was writing down all of my friends that were over 50, and then a bunch of my friends who were in their 40s were like, ‘How come we’re not on that?’ And I was like, ‘You’re too young!’ So I do have some women over 40. Because really, the whole reason for Women of a Certain Age was basically, you know, ageism for women started at 15. So, it is women over 50. But there have been women in their 40s that have done the show, too, because that’s also an age where nobody looks at you.
Inside Amy Schumer came out with a sketch called last effable day back in 2015. I don’t know if you remember that or if that hit a certain pocket for you. Where she was meeting up with Julia, Louis-Dreyfus and Tina Fey and Patricia Arquette and they were kind of dealing with the same subject. Did you feel like that handled it well?
What’s funny about that is that after I came up with the idea, everyone told me about that sketch. So then I did see it and I loved it. I thought it was really on point. What they’re dealing with, as opposed to what I’m trying to do, they were dealing with the fact that as a woman of a certain age you’re being invisible and not being effable anymore. And women of a certain age is showing people that’s part of it. Of course, we’re all very, you know, still effable for lack of a better word, but that wasn’t what this was about. The reason I came up with the idea was, there were so many women in comedy who are older who are just amazing comedians, and nobody’s ever heard of them, and I wanted to make a place for women to be able to come out and have a chance to say what they want to say. And what’s funny about the audience is, everyone just assumes that it’s an older female audience and it’s not. But you saw the crowd was mixed. Because where it was shot, especially in Brooklyn, there were a lot of people in their 20s and 30s. So you know, I love the sketch. I think it’s very funny, but I’m trying to give us more work because I think in general, once you reach a certain age regardless of whether or not you’re a female or male, the work isn’t there any more.
And as you jokingly remind us in the third showcase, everybody’s effable. But women in comedy do tend to become invisible.
Right, right. I really hope that you know, just like I after the first special came out, it seemed there were more roles for older women. Like Grace & Frankie, and Schitt’s Creek, and Hacks. And I feel personally responsible. I’m like, you’re welcome America! Because Hollywood is missing a huge market. First of all, let’s just talk relationships male-female. In every relationship the husband, basically, whatever the wife wants to do is what’s gonna happen. Do you know what I mean? So, we’re the ones that have the money because if we’re gonna go out to a show or watch a movie or something, nine out of 10 times a husband is like, whatever she wants to do. So we’re the ones controlling the purse-string, why are you not marketing to us? And now we do have our third special. It’s huge! It’s like yeah, I mean, this is the market you know, and all of those specials that I mentioned that had older female leads, are huge hits, so get with the program, Hollywood.
And now the lead from your first showcase is president of SAG-AFTRA!
You remember the Colbert Bump? I do really feel like there’s a Funny Women of a Certain Age Bump. Because all of my major stars of the show have gone on to do more stuff. Not that they couldn’t have done it without me, but it didn’t hurt.
During the comedy boom of the 1980s, you managed to have pretty much every TV credit a comedian could’ve wanted.
Pretty much. What’s interesting about that is, I remember this because my husband wanted to have children, like almost immediately when we got married in 1984. And I was like no, I have my career, my career. By the early 90s, I had done everything. And I said to my husband, ‘Well, I’m not gonna get back on any of this.’ This is how different it is in the business. I knew that I’d get back on every one of those shows, but I knew it was going to be a year because that was the rotation. So I said to my husband, let me get pregnant now. So my son was born in February of ‘92. But then I’m back on TV like two months later. So that’s what it was like back then, anything, like even club work, you were in a rotation and you kept coming back to it. It’s not like that now, because I don’t even know if there’s a road anymore because it’s, you know what I mean? Like everyone wants the next new TikTok star to be the headliner. But they have no material. They just dance and then some music happens and they’ve got 4 million views. OK, that’s what you want? OK. No problem.
Take me back to 1984 when you got married, and you told your husband that you have this career, what was your career looking like in 1984?
Well, I started stand-up in 1979 which means I’ve been doing stand-up for 42 years. Ugh. Like I like to say on stage I could have killed two people by now and be out of jail, but that’s OK. I was a young comic. Comics talk about, you don’t need even hit your stride until you’ve been doing it 10 years, so I’d only been doing stand-up five years maybe. But his mom is a Broadway conductor and one of the first people to buy Ms. magazine, so he was perfectly fine with having a wife that was gonna be going out late at night and you know, he’s a musician, so he’s in the business, too. So I would never have been with anybody that would have been like, ‘What do you mean going out till two o’clock and you’re gonna be hanging out with guys at at bar?’ I would never have married that guy. I think I dated him in high school. So we got married in 84. The unwritten rule of comedy was that once you had done everything you could in New York, which was, you know, basically doing the one-nighters and being a regular at one of the major clubs, you went to LA. You just, that’s what you did. That was the rule. That’s where you went next to get your sitcom. That was the unwritten rule. That never happened. But that’s OK. I’m not bitter at all.
Maybe you needed to be bitter if you wanted to have a sitcom. Because that’s how Roseanne got hers.
I know. I was always, look on the bright side of life. That’s not helped me. So anyway! Yeah. So I want to say, I think we left in…because this is how I do everything in life. So my son was born in ‘92. My niece is I think four years older than him. So I want to say in 1988, maybe we went to LA. And that’s when I started to do all the TV and stuff. When I talk about my past now. And I think of that girl. Age really does help you when you’re in a business like this because it’s such a brutal business. You know, when I talk about like, I wish I could go back to my young self, and say don’t take any of it personally. Because it’s not personal at all. It’s, you know, are you the right type? Do you look the right type? Is the producer sleeping with the comic’s mother? There’s so many different things. So I look back at that time. I was a regular at The Improv. I was a regular at The Comedy Store. I was a regular at The Laugh Factory. I was doing all of that, you know, running around doing spots, doing the brick-wall TV shows and everything.
When I got pregnant, I was told that I would ruin my career if I had a child. I was told, ‘What are you doing? Who’s gonna book you?’ I worked pregnant up until my seventh month, on the road. Chuckle Huts. Funny Bones. All of them, while I was pregnant. I had my son. I went back on the road. I think he was six weeks old. I took him with me and, then just continued to do stand up. The big change in my life in my career, I was a Road Dog, where I was on the road three weeks every month. And when I would leave because I’m in Los Angeles, and I had to go back to the Midwest and the East. I would wake my little boy baby up and he was two or three years old, he would sob. he would be like ‘Don’t leave me Mama!’ To this day he still knows how to get me to feel guilty. I was in Las Vegas at the Riviera comedy club and I was getting, you know, kinda especially the old road comics, we would take pictures with us to put up. I was putting everything away and I’m getting my hotel room where it feels like home. And I remember saying to myself, you know, God wouldn’t be good if I just didn’t have to do the road but I could still do comedy? And the next day I got a phone call from the entertainment director at Riviera saying that the comic who was next door, working in the burlesque show, she was gonna be out for the summer and did I want to replace her? And that turned into you know, the 10 year run in Las Vegas.
And that was also a time when Las Vegas changed. I’m a certain age, too, so the first time I visited Las Vegas, in 1993, I remember that’s just when it started to change from the Rat Pack and Sin City and a place adults went to becoming family-friendly. Of course, it didn’t take too long for it to shift again to the “Whatever happens in Vegas, stays in Vegas” mantra. What was it like performing there during this transition?
I totally forgot about that. I’m glad you brought it up. That it became family-friendly for like a minute? Because I remember, this is before I was actually working and living there, The MGM Grand decided they were going to change the theme of the hotel to The Wizard of Oz. But there was a statue of Dorothy and the characters right out front. They had childcare. By the time I got there, to live there, it had already started to change. My son was four when we moved there. So ‘96. By the way, I always love telling the story about Vegas. The entertainment director of the Riviera when I got my gig was Steve Schirripa.
When I hear The Riv, I think of Steve Schirripa.
Exactly. And he’s like my guardian angel, you know, we’re still close friends to this day. He’s always looked out for me. So when he called me and said, ‘Do you want to do this for the summertime?’ I said of course, because it was great money and you stay home, but I said I have to bring my kid. That summer, before I actually signed a contract and stayed there. We lived at the Riviera, me and my son lived in our hotel and every morning we’d go have breakfast in the cafeteria, and then I’d bring him to the pool, and because he was four years old, he thought this is great! It was a wonderful time. But there was no childcare anymore in the hotels because it had already changed. So I found the one preschool that had childcare til midnight. It was like a preschool but then because so many people worked at night and they have kids. So on Saturday night, because we had three shows, I had a friend of mine watch my kid, because I couldn’t get to them. If I didn’t show up at 12 o’clock, they’d put them out on the street!
When did you feel like you had hit a certain age as a woman in comedy? Was it after leaving Las Vegas?
That’s a really great question. So we stayed in Vegas for 10 years. So at this point Layne is 14, so I was 48. We wanted to move back to New York City because my son was got accepted to a really great private school here in the city. And, that shows you how bad the schools had gotten in Vegas that I’d rather have him go to school in New York City, because they had great schools up until they changed superintendents and it started to get bad again. Anyway, so we ended up coming back to New York, so I’m 48 years old. And this was so bizarre to me, Sean. I’d been a road comic up until I left Vegas. Working constantly, the same clubs, same two dozen rooms. And all of a sudden I come back to New York, and I’m not considered a national headliner anymore. That’s when the tide started to change for road comics like myself. Because in 2006, the Internet was happening. There were all of these other ways to do comedy and so all of a sudden, I wasn’t getting the work anymore. Mixture of the Internet happening and also my age, so that’s around 48. When I first got back here, I started to see the writing on the wall, so I started preparing myself. Because I wasn’t gonna stop doing stand-up. There’s nothing else I can do. I’ve tried. I really have I have no other skills than comedy. So I started to develop solo shows. I started to direct. I started to teach. I didn’t come up with the idea for Funny Women until I was 57. So it’s a type of thing where I’m like, OK, I had to start juggling some of these things. Otherwise, I’m not gonna have a career.
So you just said it took you almost a decade after you came back to New York before you figured out what the next iteration of your career was. Who was telling you that your resume didn’t mean anything? Bookers? Agents? Managers? Casting people? All of them?
All of them. ‘They said, You’re not a national headliner anymore.’ And most of my credits were still major, major credits. Yeah, it was all of it. It was the bookers. It was the people who were booking me, it was the agents and the managers. I just couldn’t understand. I was like, What are you talking about? I was starring in two different Las Vegas revues, and I had dozens of credits before that, and you’re telling me that no one’s gonna come see me. My husband figured it out because he’s one of those numbers people. Just at Crazy Girls alone, which was the first show I did in Vegas. I was probably seen by 5 million people, because we were doing 13 shows a week for five years. And you’re telling me all of a sudden no. It was mind boggling.
Because now you go on a show like America’s Got Talent. And the prize for that is they send you back to Vegas.
Exactly, exactly. So it’s a totally different time now to be a comedian.
How did you not quit, in that period between 48 and 57?
Well, I’m a stubborn, stubborn person. I didn’t quit. There were a couple times that I was like, I don’t know if I could do this anymore. And I think every comic who’s been doing it a long time says that. There was a tiny blip in, I want to say five years ago, where I worked behind the scenes and I was working as an agent for a touring company, because my husband’s mother had had a stroke. And the office was a block and a half from my apartment. And I figured out that because I couldn’t go on the road. My husband works on Broadway and he was in the middle of rehearsals for the opening of School of Rock. So this is how long ago this was because he was there for the entire run. So he was gone all day. So I couldn’t go on the road, because if something happened, there’s no way he could leave. So I was like, You know what, I’ll take this job. God forbid there’s a problem, I can get right out. So I did do that for about six months. And one of the reasons I’m really glad I did this. I’m glad I worked on the other side, because it really prepared me. I learned so much about the business on the other side. It was really great. I learned so much about it, but I realized I was like if I’m working this hard for other people. Why don’t I just do this for myself? And that’s when I went back to stand-up full time.
Funny Women of a Certain Age started as a live monthly show, right? And when when did you start doing that?
OK, so I was doing a podcast. And we had the best time. It was all other comedians and we just had the best time. We were laughing and telling war stories and stuff and I was coming home from the podcast and I called my husband. I said, I know so many women my age and older that are still in the business, still pounding the pavement. This should be a show.
I knew it was something when he went, this is a really good idea. So I started talking about it. Do you remember the Cinderblock Festival, that was a couple years ago, It was in Brooklyn. So Coree Spencer and I, she was the woman who created that festival, we’re talking online and I said I’m doing the show and she said, ‘Why don’t you premiere it here?’ Because I hadn’t done it yet. I had not even done a live version of this. I just had the idea. She said Judy Gold and Janeane Garofalo were going to be part of the festival and they’re older comics, so then I added myself, Rhonda Handsome. As a joke we had a millennial host it. We did the show and it sold out and everybody loved it. Everyone’s like, this is a great idea. And then somebody who was working at the festival said, Oh, I work at the Kraine Theater. I think my boss would love the show and she hooked me up with him. We did a we did a show in December of 2017. And he offered me a residency. He said I’ll give you a monthly residency. And we’re starting our fifth year next year.
So it started the residency in 2017. And then the first Showtime special came about by 2019. So were the gears already in your head in terms of how to turn this into something or circumstances just made it possible.
You know what? As somebody who has been in business a long time, you know that everything takes forever, right? This did not. That it happened so fast was mind blowing to me. So we did the showcase in December. A gentlemen named Dave Goldberg from Killer Bunny, he did the shows for Gotham Comedy Live. His was a production company that ran those shows. We had met years ago because I’d helped him produce a comedian named Shang Forbes. I was supervising producer on Shang’s special. That’s how we became friends. Dave’s like my kid brother. You know what I mean? Just from the moment we met, we’ve been friends. And whenever I had an idea for anything, I always go hey, I’ve got this idea and he would check it out. And even when I was working as the agent, we’d throw ideas back and forth. I come up with this idea. And I said to him, I said hey, I think you should come see the show. And he came to the show and he said this should be a TV show. So we do a showcase at the Kraine in February. So Dave already liked it before he even saw the show. He said this is this is absolutely a TV show. We met with Showtime. They liked the idea. But you know Showtime doesn’t do a lot of comedy, the way Netflix does. They basically do like maybe six, maybe eight specials a year. So there was no room for us. So when we did the showcase in February, everybody was there. HBO, Showtime, Lifetime, we had CNN there, they were think about doing documentary. Amazon was there and everything.
I did not tell the ladies that this was a showcase, because you don’t want to tell comedians that you know, a lot of stuff is on the line. Veronica Mosey, Leighann Lord and Vanessa Hollingshead. And it was all industry and there happened to be I want to say I don’t know what which network they were from, but there were three women in the front row who young girls, and Vanessa just blew the house off. I mean, she just went after them and just it was it was a magical moment because the Kraine is a tiny tiny theater. And you could just hear the laughter reverberating. It was an amazing night. And Showtime was there and pretty much, Showtime was interested. Amazon was interested. I’m sure there were other people. I can’t remember. I just remember at one point, Amazon was thinking of possibly putting this on as like a sister show to Mrs. Maisel. In the end, when we had all of these different offers, I said look, Showtime gave me my first break. When cable was new, HBO had the young comedians and so Showtime wanted to do something like that. So they had the comedy club network. So the comedy club network basically went to different clubs all over the country. They shot it and it was a series and then every year in the clubs and then at the end of every year they have the All Stars, so I ended up being on Showtime’s The Comedy Club Network All Stars 6, and that’s the one that Don Rickles hosted. Somewhere I have a picture of me and Rickles that I cannot find. Someday I’ll post it. So I said I want to go with the network that gave me my first break. And that’s why we ended up with Showtime. They got the show from day one. From day one. They let us do whatever we want. It’s kind of really awesome.
And you’ve done it three years in a row. So does this mean that you’re already hard at work on next year’s special? Or have you not thought about this as something you do every year for the rest of your life? I mean, who knows what Showtime will be like next year, even.
Of course, I would love to do this every year. You know, I think that the longer we do this, there’s even more comics that become eligible. I would love to. I mean, sure, absolutely. You know, but ratings have a lot to do with it. What the world is, you know, I would love to do this where we shoot six of them in a week, so we have them. Because we did the first special in 2019. And then we shot the second special that same year. The first special aired in March, filmed the second in October in 2019. Then the pandemic hit and nobody knew what was going on. So I keep going, well if we put a bunch of them in the can and if God forbid, somebody eats a bat. We have some more content for because, remember during the pandemic, everything was shut down. Nobody had content. So I keep pushing for it. I mean, I will tell you my wish list of course, you know, I mean, if I could get Lily Tomlin, then I’d be done. Like alright, I’m done. I can quit now! I met Lily Tomlin. I would love to have her do one of them or even Betty White, but you know, she’s gonna be 100 soon.
That’s precisely when to get Betty White!
I would love to and I do think you know, every time we do one of these shows, everyone is so great in the audience. They’re so happy to see these women who’ve been around, some of them people know, some of them don’t know. But these are all great comics. You know what I mean, Sean? When you go to a comedy club now, sometimes these newer comics, they’re like, so what do I want to talk about now? OK, no. These women, they came up. You introduce them. They do their job, and they get off. There’s no fat to the joke. Everybody just kills and the audience keeps laughing. Why not have more of that? Why not?
Marsha Warfield also did you a great service in shouting out your branding as “National Mom.” So, in that spirit, at this certain age, do you get more out of promoting other comedians, then your own career? Does that mom aspect carry over because not only are you giving these women a platform, but you are remembering to give yourself a 12-minute set, so that’s good on ya. But then also you mentioned Shang, but you’ve also worked with other comedians on their specials or on their one-person shows. So at this age, do you really get more rise out of the maternal aspect of helping other comedians?
Well, what’s funny about that, it’s interesting that you mentioned the thing about me being in every show, and honestly, that’s not me, that’s Showtime. They said this is your show, and you need to be the thread or whatever we call it. Which is to me, it’s like OK, you know, I mean, because I have no ego about this show, you know what I mean? Like, so I could have easily not on the show, but they were like we want, you’re the face of the show. So that’s why I’m on it. And the material you say? That was brand new stuff. I wrote that during the pandemic because I don’t remember my act. I had done my act in over a year so I sat down with my husband who writes for me, and Vanessa Hollingshead and a bunch of other comics and I said, we have to write me a new act. And I had to do these all of these on Zoom. It was like it was a 20-year-old comic again, Sean. I went to every crappy bar show in the city.
But to get back to your question, I love helping people. Probably early on in my career, it was a detriment. But I’ll run into comics that I don’t even remember when I was a road comic, who’ll tell me, ‘You let me sleep on the floor. Because the booker wouldn’t give the opening act a hotel’ and, you know, I’m like, well, that’s not going to work. You’ll have to sleep on the floor with me, you know? I don’t know how not to help somebody. So I do love performing. I’m having a lot of fun now because I never considered myself a writer. So the fact that I sat down and went OK, I don’t remember my act. We have to write 10 new minutes for television, and it worked as well as it did on the special is thrilling for me.
But to see these other women shine brings me more joy than anything because yeah, you’re probably right. It’s the maternal thing. My son’s grown now, you know, he sees a grown man, you know, he doesn’t need me as much. So I like that. You know, and I was watching. When we go into the editing. I watched the shows. The one thing that didn’t like about the Irvine Improv and they were wonderful, but there was no place like in the Bell House you could be backstage and go through a hallway and sneak in and watch. There was no place for me to do that. So I never got a chance to actually see the women. I heard them because I was standing in the back listening. So to watch these women, and every single show this has happened. They shine, like wow, look at that. Because they know that because I’ve said to them, you do whatever you want. There’s no judgment. Do whatever you feel is your funniest and they all came through so that’s amazing.
So I’m doing the taping, right? The audience was amazing. And I’m not one of these comments who go, I kill all the time — I’m having the set of my life. The set. I mean, everything is just hitting and nailing and applause breaks. All of a sudden I look to the right of me and I see my director, she’s waving her hands frantically, and in my head. I’m thinking to myself like because you know as comics will tell you this, how we we think and we’re doing our act but we’re also thinking, and in my head I’m doing my act. And I remember thinking to myself, she shouldn’t be over there. She should be in the sound booth in the back. I’m having this amazing set and I see her out of the corner of my eye, and finally I just stop and I go, ‘What do you want?!’ and she goes, there’s a light, it blew out behind you. We have to stop the tape. Nobody’s hearing this. The audience is like what’s going on? And I said, What? Now I said come out and she’s a director, she’s not used to being on camera, so I give her the mic. She goes the light blew out. We have to stop taping. We have to redo it. So I go OK, and I look at the audience I said listen, this is a TV taping. So you know this happens. I say so we’re going to start from here. And then we’re going to do it again. And then she goes, ‘No, you have to start from the beginning.’ So now I’m like… after a few choice curse words — the audience is hysterical laughing because I’m like at this point, I am cursing like a sailor Are you effing? Are you just? And she’s just standing there like, wide-eyed because she doesn’t want to be there, and I know. So I said OK, and I explained to the audience that here’s what happens. It’s a TV taping. We’re gonna redo this, but you have to act as if you’ve never heard this before. This is all adrenaline because if I had had a moment to think about it, I would have said somebody get me a razor because I’m going to go slit my wrists now. Do you know what I mean? That’s gonna be a whole other series. But it was so mind-boggling and I went, give me a second. You have to give me a minute because I have to. Just in my head this was like I don’t remember any of act! I don’t remember a thing! And that’s why I said give me a minute and I just I went OK, hold on a second. Let me just take a moment and see. And I took a moment. The audience saw me take the moment, which I think is why it ends up being the set you see. And I did. I took my moment and started as if nothing had happened. And they could not have been kinder. They laughed more the second time. It was amazing.
I guess this is when I should tell you that I forgot to hit record. So we’re going to have to start this from the beginning?
Oh I will!
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