Conversations: Carole Montgomery
Comedian looks back on 45-year career and ahead to more 'Funny Women'
Carole Montgomery spent 20 years living on the West Coast, but she’s a New Yorker through and through. Fearlessly unafraid to call things as she sees them, she is funny, brash, kind, loud, thoughtful, ballsy, observant, profane, and caring.
“If I ever get off my ass, I’m going to finish my one-woman show,” Montgomery says at the start of an hour-long conversation that looked back on her 45-year career as a standup comedian. “I’m calling it ‘I Am My Father’s Son’ because I really am my father.”
Montgomery is the creator of Funny Women of a Certain Age, a showcase that started in 2017 as a chance to work with her friends and has since led to a ongoing tour and three specials on Showtime. The roster of comics, all over the age of 50, who have taken part in the shows includes Fran Drescher, Janeane Garafolo, Caroline Rhea, Marsha Warfield, Carol Leifer, Julia Scotti, and Leighann Lord.
Carole and I have known each other since 2010, when our son, Ben, joined the Broadway cast of “Billy Elliot.” Carole’s husband, Todd, is a musician (as is their son, Layne) and was working as one of the child wranglers on the show. We hit it off — at one point, Ben lived with the Montgomerys for a month while in school and on a break from the “Billy” tour — and have remained in touch over the years.
I decided to have a formal “Conversation” with Carole after she left the Meta apps, where she was a consistently funny presence, and joined an exodus of comics to Substack. Our hour-long talk has been edited for brevity and clarity.
Post-inauguration, a number of creative types like you have left the Meta apps and made the jump to places like Bluesky and Substack. One reason is Mark Zuckerberg is one of the numerous tech titans announcing fealty to the current administration. Why did you leave?
It’s not harming him at all, but it makes me feel better. And honestly, for me, social media is not really my demographic, except for possibly Facebook. They're not on TikTok. They're not on Instagram. It’s not going to hurt me as much as it will for a lot of people.
Where did you get the idea for “Funny Women of a Certain Age”?
I was doing a podcast with other, older female comics in the summer of 2017. We weren’t drinking, but we were all sitting around eating and talking and laughing our asses off. Afterward, I called Todd and told him I’d had the best time on this podcast, and said we should do a show where it’s just female comics who are friends and take it on the road. For the first time in my career, Todd said, “Wow. That’s a really good idea.”
Everyone in show business has brilliant ideas and they never go anywhere, but it stuck. We premiered at a mini-comedy festival in Brooklyn with Jeanine Garafolo and Judy Gold, and a young lady who was working at another theater came up to us afterward and said her boss would love the show. We did a showcase for him and then did shows at his theater once a month for six months. Then we did a big Hollywood showcase and got the deal from Showtime.
It was so fast — 18 months from that podcast to filming the first special. That shit doesn’t happen.
Who inspired you to become a comic?
My father. Most people blame their fathers for, you know, their emotional lives. I blame him for my career choice.
He was In the Korean War. When he got back, he wanted to be a performer. He was very loud. When my father walked into a room, he walked into a room. But he got married just like everybody in that generation, went to NYU, got his teaching degree, and from then on was a high school teacher. On the weekends and during the summers, when I was between 5 and 10, he was a bartender in the Catskill Mountains.
I would sit with him while he was setting up the bar at the club. The stand ups — Totie Fields, Jack Roy, (aka Rodney Dangerfield), and Jack Ross, the actor from “Car 54, Where Are You?” — would walk in and talk with my dad.
I’d watch these people do soundchecks, so I was always around it. So, shockingly, of course, I became a comedian.
When did you know this was what you were going to do?
I was doing summer stock at Playhouse on the Hill in Utica, N.Y. This was the summer of 1979. I was just out of an abusive relationship, and I didn’t know what I wanted. A friend mentioned that I should be a comedian and worked on five minutes with me for a Christmas in July party.
I did those five minutes and realized it was my calling. I got home — I was still living with my parents — and started taking a bus to Pips on Sheepshead Bay for open mic nights. And the rest, as they say, is history.
Comedy was so different than it is now. There was no Internet. The only way you could prove yourself was to be on stage. There was no TikTok or Reels or any of that. Basically, the rule was you stayed in New York until you got good enough, either by working the clubs or by doing shitty one-nighters. I did a lot of those before we moved to L.A.
Which comics influenced you?
Richard Pryor, George Carlin, and Lily Tomlin. Those are probably the top three. But Richard is the one I always go back to. Jonathan Soloman, a friend of mine who’s now a TV writer, and I went to see (“Richard Pryor: Live in Concert”) at a theater on 42nd Street in the late 1970s. and that movie changed my life. I was like, “Oh my God. This guy. He’s funny and fearless.”
Did you ever get to meet him?
It’s one of my favorite memories. I was a young comic at The Comedy Store. I was in the original room, not the main room. After my set, this very, very big man comes over to me. He was obviously someone’s bodyguard because he was all buffed and had guns, so I paid attention.
He says, “Excuse me, Mr. Pryor would like to speak with you.” And he brought me over to Richard, who was sitting next to Mitzi Shore (owner of The Comedy Store).
Richard leaned in. This is when he was very sick (Pryor had multiple sclerosis and was confined mostly to a wheelchair), but he leaned into me and said, “You’re very funny.” And I looked and Mitzi and said, “OK, I’m done.”
I ran out of there and started crying. I called Todd immediately on a pay phone, and he was like “What happened? What happened?” I couldn’t speak because I was so overwhelmed that my hero had seen me, and he thought I was good.
What’s funny is that it’s just a memory. There’s no photo of me with him. But I’ll never forget that day because I was so young in the game then.
When you were coming up in the business, male comics were the norm and women in the business were the exception. I’ve read and heard a number of tales about misogyny and the privilege of male comics, especially from the 1970s to the 1990s.
There weren’t a lot of women when I started. Now there are thousands of female comics, and usually there’s still only one woman on the bill — maybe. I don’t know what’s going to change it.
And the misogyny is still there. It will always be there. Right after the pandemic, in fact, there were no female comics on in all of the L.A. clubs on the weekends. I was like, “What are you doing? Did we go back to 1957?” Thankfully, people like Patton Oswalt, who’s very pro-women, got involved in it and called it out. But it definitely still exists.
When “Funny Women” started, I waited to see which of the misogyny boys — that’s what I call them — was going to bash the show. Maybe because they all know me, nobody from that group of guys had a bad to thing to say about it.
They all respect me. At the same time, they also know I’m not somebody to fuck with. Between the respect and the fact they didn’t want have their balls ripped off, I think I got better treatment than most.
One of my favorite Ben lines from the time when he stayed with you: “Dad, I think Carole has bigger balls than Todd.”
The running joke we have is that Todd gave me patience and I gave him balls. That’s what you do in a marriage. Give and take.
You’ve been married 40 years. How did the two of you get together?
There was a club on 33rd Street and 3rd Avenue that’s no longer there. It was a restaurant called Good Times, and they had a room in the back where they were doing comedy. I was doing a show there one night, and a fellow comic brought his cousin, Todd, to meet me.
It’s the only time I really acted like a girl. I was so flabbergasted by Todd that I went, “Oh wow. Great to meet you. Excuse me a second.” And then I went into the bathroom and took an hour to redo my makeup and comb my hair, which I never do. By the time I was done, Todd had left because he thought I didn’t like him.
We ended up meeting again a couple of months later and that was it. We’ve been together ever since.
Talking about your career arc, you made the move to Los Angeles in 1986 and stayed for 10 years. You also had your son, Layne, while in L.A. What was that period like?
L.A. was where I did all of my early television stuff, and after a while, I started doing sets at The Comedy Store. I was just a cute little blonde who tried to look like Kathy Rigby. I figured, I’m in Los Angeles, I must dye my hair blonde.
How long were you at The Comedy Store?
Probably 1990 to 1996. One of the great, nice things is my name is on the wall. I’m listed as one of the original Comedy Store comics. That’s pretty nice. I can send you a picture if you want. I’d have to find it, of course.
(Sighs) That could take a while.1
Ten years in Los Angeles, then 10 years in Vegas, working at The Riviera, Crazy Girls, and Midnight Fantasy. That life makes me want to ask you about “Hacks” (the Emmy Award-winning sitcom starring Jean Smart). I love the show, and it seems to capture Vegas well, but the worst parts to me are the standup routines. Why is that?
It's funny. No one has ever really been able to capture stand up as a character. With (“The Marvelous Mrs. Maisel”) it’s the same thing. Both of those characters are played by actresses who are great at playing a comedian. And I love both of them, especially Jean Smart. I just adore that woman.
But to the people who write the show, I don’t think the stand up is as important as the story between the characters. Carol Leifer, who was on my second special, is a writer on the show. And if anybody knows how to write standup, it’s Carol. Standup is the backdrop. I just don’t think it’s as important to them as the actual relationships.
In some respects, standup has become a form of “legacy media,” like print journalism or photography created in a darkroom.
That’s a good way of putting it.
We’ll probably have AI standup before too long. And it will probably be as funny as the standup routines on “Hacks.”
Oh, that’s coming, I’m sure.
In what other ways is the world of standup different now?
It’s always changing. And lucky for me, I'm not an old person that goes, “I'm gonna just stay the way I am.” So many comics say, “You know the way it used to be…” and I say, “Yeah I know,” and I keep moving. You have to bob and weave, and you have to change with the times.
One thing I always say is, “I’m a comedian. I want to get on stage. I want to tell my jokes. I don’t want to be a producer. I don’t want to be an editor. I don’t want to film my own sets. I don’t want to be on social media.” But if I have to do that to tell my jokes, I will.
Back in the day, it was about being on stage in a smoky room like you see in “Maisel,” when she was working on the strip shows. That’s what I did at Crazy Girls. I was the comic between the girls who didn’t have their clothes on. And that’s where standup works best, in a place that’s dark and dirty. I joke that I plan on being cremated, but I would like my tombstone to say, “I’m always in the fucking basement,” because every club is literally in a basement.
Well, you could say, “Cremate me and put me on a shelf because I’ve spent my entire lifetime in a hole.”
(Laughs) Exactly.
When you're building a new set, how do you do it? Do you script everything? Do you improv it?
I'm a very odd comedian. My comedy bestie, Leighann Lord, writes every day. I’m not that person. Sometimes it takes months for me to sit down and write new material. I have to have the urge. Something will happen and I’m like, “Oh, shit.” And then I start writing.
During the pandemic, I was like, “Our lives are over.” I literally did nothing for two months and gained like 800 pounds. And Todd, I love him to death for this, said at some point, “Carole, this is going to end. And if you want to get ahead of the curve you better start writing new material.” He helps me write a lot, and we started writing it together.
It was mostly pandemic stuff, but Todd was right because that’s when we ended up getting the third special (that aired in 2021), and my material was focused totally on what was happening at the moment. It's really about just trusting your gut and jumping in.
Republicans have co-opted the word “censorship” and weaponized it, even as they’re trying to censor everything in sight. The corporate response has been to scrub all overt references to anything that does not meet the Christopher Columbus round world version of history. As a comedian, how do you deal with all of this?
I do what I’ve always done. My little dick jokes. I’m not worried about “censorship,” but I know some comics who are.
What’s does the future hold? I don’t see you retiring anytime soon.
I’ve been writing and I have some new material. I’m also going back through some old writing and jokes and looking for ways to refresh some of that material again.
A lot of people want us to revive “The Golden Girls.” There's something there, but there’s so much going on in my brain, I’m not sure I have the bandwidth anymore. We’ve got dates already for 2026, and my agent's like, “Did you book the cast yet?” I haven’t booked the dates for September yet because my brain doesn’t want to do that anymore.
And when you reach a certain age, you don't know who's going to be still living or dead in a year.
That's very true. I don't know if I'm going to be alive in 2026. I don't know if the world is gonna be around in 2026.
In many respects, you have made this career because of and in spite of everything. How?
I don't take no for an answer. I never did. So many times, I was told, “You can't do this because you're a woman. You can’t say this because you're a woman, or you shouldn't do that because you're a woman.”
I'm like, “Watch me.” Most people run away from conflict. I run toward conflict like a moth to a flame. Which is probably why this whole administration is so infuriating to me. It's like, seriously? You're gonna tell me I can't do something? No way. I just keep my head down and keep going, you know?
She found the photo…
She's a pip! I'd have a hell of a good time in the audience, or at a high top.