For more than 40 years, Caroline Hirsch’s name has been synonymous with comedy in New York City. Beginning in 1981, when she opened a small club bearing her first name in Manhattan’s Chelsea neighborhood, comedy’s greatest performed on — and in some cases, made their bones on — her stages: Dave Chappelle, Jerry Seinfeld, David Letterman, Jon Stewart, Gilbert Gottfried, Jay Leno, Kevin Hart, Bill Burr, Paul Reubens and Michael Che, among many others.

In 2004, Hirsch and her partner in business and life, Andrew Fox, decided to expand the Caroline’s brand beyond the walls of the club (which had since moved to Midtown Manhattan). The New York Comedy Festival debuted in November of that year, spanning approximately 15 shows over five days. On Nov. 7 the festival kicks off its 20th season which will feature more than 300 shows over 11 days, including its annual Stand Up for Heroes benefit — now in its 17th year — where Bruce Springsteen, Jim Gaffigan, Seinfeld, Stewart and other comics and musicians have raised a total of $84 million for wounded and ill military veterans. There’s also The Eras Tour: Taylor Swift Comedy Show and Dance Party.

“Twenty years is a long time to be in business, especially in New York City,” says Hirsch — who, along with Fox, spoke to Billboard about how the festival and comedy have evolved over that time.

How has the festival evolved over the last 20 years?

Caroline Hirsch: Most noticeably is the depth and length of the festival. We started out with 10 big shows and three or four headliner shows. Now, the festival is 11 days, with over 300 shows and 22 headliners. And I would attribute a big part of that to the fact that comedy is more of a staple in our lives today.

Andrew Fox: When we started, so few comics playing theaters. New York has such great theaters — Carnegie Hall, the Beacon Theater and Madison Square Garden. For comics, these are bucket list shows.

Hirsch: Before 2006, the only person who played Madison Square Garden was Andrew “Dice” Clay, and that was because of his relationship with Howard Stern. In 2006, we put Dane Cook into Madison Square Garden for two nights. We sold 38,000 tickets. Since then we’ve put Kevin Hart, Bill Burr and Trevor Noah at the Garden.

Fox:  When we played Dane there, it really changed the way people looked at the comedy business. When we look back at that, from our humble beginnings. It was a game changer for us, agents and managers in the industry.

Hirsch: Now Carnegie Hall is considered a steppingstone to the Garden or other arenas. A lot of comedians we worked with at Caroline’s wanted to play bigger venues. The festival enabled us to do that. And we continue the tradition started at the club of building talent. Zarna Garg started with one night at Carolines, and at this year’s festival, we’re presenting her at Town Hall on the last day of the festival.

You closed your club in at the end of 2022 because your landlord wanted a significant rent increase. Do you have any plans to reopen it in another location?  

Hirsch: The festival is about moving beyond the four walls of Caroline’s and doing comedy in a bigger way. The only way we’re thinking of Caroline’s right now is as a bigger event.  

Fox: People are always coming to us with different ideas for events and branding opportunities, and we listen. Consumers trust us if they’re not familiar with a particular performer.

Caroline, you recently wrote an op-ed in the New York Daily News about comedy being more important than ever given today’s political climate. Can you talk a bit more on that?

Hirsch: Comedy is important for society, and it has become a central part of our conversation today as you saw with some of the stuff that came out of the political rallies. Joe Rogan’s podcast had a lot of influence during the presidential campaign, and I’m curious to see what Bill Maher’s play is. Bill’s in the center, and he calls it right on. I think hearing what he has to say will bring relief to some people.

You’ve also said that it has the power to bring people from different backgrounds, political and cultural perspectives together.

Hirsch: Ideally, comedy is about taking information that may be controversial or polarizing and making it more palatable in a communal setting where everyone comes together to laugh and let off steam. We live in a country where 50% percent of people are pissed off, and 50% are happy. How do we bring those two sides together? By making them laugh. Laughing is a healing process. It soothes the soul.

Andrew, in another conversation, you said that stand-up tours are hotter and more important then ever for comics’ careers.

Fox: People are getting their comedy in all different forms today, including social media and streaming and podcasts, but there’s nothing like the live experience of sitting in an audience, on a date or with friends.

Hirsch: It used to be that everybody wanted a sitcom. Now they want to tour. And for comedy fans, it’s like going to see a band. People want that first-hand experience, and they’ve wanted it more since Covid.

How has stand-up comedy changed since the festival started?

Hirsch: It’s a lot smarter, much more political. It used to be very left-leaning, but now it’s more balanced. There’s a right-leaning side to it now. Women play a much bigger role in comedy now, too. Also, the number of headliners has increased. In the early days, I had maybe 18 headliners. Today, there must be a hundred comics that can headline. I think Caroline’s had a lot to do with that growth. We also played a role in the media’s increased interest in comedy. In the early ‘80s, no one covered comedy. I had to convince people to cover it at the [New York] Daily News, Page Six and on the Howard Stern show.

Is there one particular show at the festival I should not miss if I want to see comedy’s next headliners?

Hirsch: New York’s Funniest. Every year we survey the canvas, so to speak, and select 10 promising comics to participate. Some major comedians have come out of it — Nate Bargatze and Michael Che won in different years. It continues to grow year after year, and it’s a way for comedians who aren’t know to get known and to get agents and managers. The night Michael Che won, he got an agent and a manager at the bar at Caroline’s.