How Caroline Hirsch Turned a Cabaret Into New York’s Hottest Comedy Club

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In ELLE.com’s monthly series Office Hours, we ask people in powerful positions to take us through their first jobs, worst jobs, and everything in between. This month we spoke with Caroline Hirsch, the woman behind the legendary comedy club Carolines on Broadway in Times Square. Originally a cabaret, Carolines pivoted to comedy after Hirsch witnessed the rise of observational humor in the ’80s. Even though she’s known for discovering talent like Jerry Seinfeld and Billy Crystal, Hirsch doesn’t consider herself funny. “No, not stage funny, no,” she says. Outside of the comedy genre, she’s taken up other pursuits, including developing a documentary about the history of anti-semitism, based on the book A Convenient Hatred: The History of Antisemitism. Ahead of the New York Comedy Festival, where 200 comedians—including John Mulaney, Hannah Berner, and Jenny Slate—will perform at over 100 shows around the city, Hirsch discussed how she got her start in comedy and what she’s learned along the way.

My first job

One of my first jobs was a market rep at Gimbels in the central buying office. Every day, I would go out in the market and see what was new and what was trending. There was a sales person there who would call me up and go, “I have this new top and it’s selling out everywhere—you should really come over, see it, and place an order for it.” I was the person that collected the product for all the out-of-town buyers. I went on shopping sprees in California, Italy…Italy was a big place for scarves—there were a lot of orders there. I remember one popular item at the time was this Ells Belles shirt at 1407 Broadway. It was a jersey knit top with a beautiful print that came in many different colors. That was a very, very hot item.

How I fell in love with comedy

Like a lot of comedians in the ’80s, I was influenced by George Carlin. Back then, observational humor was a whole new genre of comedy that had originally started with him—talking about things that are common to all of us: things we experience during the day; everyday things that we all laugh at because it happens to us.

Why I decided to open a comedy club

When Gimbels went out of business, I didn’t have a job, so I took some time off. Then some friends of mine approached me to help them open up a cabaret, so I invested some money and we opened this club and they called it Carolines. It was on 26th Street and 8th Avenue, and it had about 110 seats. After about a year, something just wasn’t clicking. But we were all big fans of comedy. I loved The Late Show with David Letterman, and Jay Leno was on all the time, so I said, “Why don’t we hire Jay Leno?” After he came into the club, he went on Letterman and said he was at Carolines in New York City. That put us nationally on the map. When word got out that he was there, then we hired Jerry Seinfeld, then Garry Shandling. We kickstarted Billy Crystal’s career. Larry David had a Sunday night show where he would perform all the SNL sketches that never got greenlit.

My work philosophy

I did everything by the seat of my pants. I created a PR movement; I went out and hustled reporters to come to the club. When I committed myself to [Carolines], I wanted it to work, and I knew we were onto something because the people we were hiring were very exciting. I wanted to get the word out, and I wanted to elevate comedy to the right rung on the ladder as an art form, because it was not appreciated at the time. Nobody realized the potential of Larry David, Jerry Seinfeld, and all of the great comedians.

Best career advice I’ve ever received

When I worked in retail, a big-time merchandise manager said to me, “When a salesman calls and wants to show you something, always have respect and see what they’re selling, because you never know when that’ll be the greatest item around that will fly out of the stores.”

The biggest lesson I learned starting my own business

I know what works. I know what people want, because I sat in a room and I watched peoples’ reactions, and what’s good is good. After 40 years of watching people onstage, I’m in tune to feel what people want.

On what makes someone funny

Usually, comedians have big personalities to begin with, but it’s how they look at a subject and how they think about it and how they define it that makes it funny. Taking certain stereotypes we all know and talking about it in a certain way. It’s that community of laughter that makes it funny.

My advice for aspiring entrepreneurs

I’ve always been kind to people. I never say to anybody, “You’re not funny,” because that’s just not true. If a person wants to be a stand-up comedian, they need a lot of practice, and they need good material. I learned early on to be open to everything around me, never say “no,” and just listen. Also, you have to have tenacity. You have to really have a conviction for what you’re doing. And as long as you have the conviction, even if it doesn’t turn out [well], your intentions are all good. You’re there and you’ll figure it out. Maybe you’ll have to turn something around a little bit so it works, like I did when the cabaret wasn’t working, but I turned it into something that I thought might work, and it did work. After we started to sell out a number of shows, we knew that we were onto something. Whatever it is, stay with it, work hard at it, and devote everything to it. Give it a try!

What I love most about my job

Looking back and seeing how successful everybody that I worked with has become. When I watch TV and I see everybody and we all kind of grew up together, we all worked together, and where everybody’s come to right now. I had a TV show on A&E from ’90 to ’96 called Caroline’s Comedy Hour, and Michael Patrick King was one of my first writers on the show—him and Jon Stewart—and it was so much fun to see Michael, way before he was a producer, taking control. Judd [Apatow] also did Caroline’s Comedy Hour in 1990. He was in high school at the time, and he went around interviewing comedians. He lied to get into the club! He snuck in, and I caught him.

My favorite memory at Carolines

The first time Paul Reubens performed [at Carolines], I remember Andy Warhol coming in with a whole group of people. He was wearing pajamas. I will never forget that. He was way ahead of that trend.

Why comedy is so critical right now

A lot of independent venues in the United States closed down when COVID struck, so it’s important that we go out and support all of the smaller venues. That’s where people get their starts, that’s the real creative process where people get seen, and where they get popular, and where they sell out when they become popular. Carolines’ mission is to keep developing new people. Comedy is important because it makes people feel good.

This interview has been edited and condensed.

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