Comedian Brian Regan has spent years touring the country doing stand-up and made quite a name for himself: he appeared on The Late Show with David Letterman 28 times and has been featured on The Tonight Show with Jimmy Fallon and Comedians in Cars Getting Coffee, Jerry Seinfeld’s popular web series. In September 2015, he performed at Radio City Music Hall in the first live broadcast of a stand-up special in Comedy Central history; that same month, Vanity Fair called him “the funniest stand-up alive.”

This month, Regan will appear in Sarasota at Van Wezel Performing Arts Hall. We caught up with him to find out how he writes a joke, his thoughts on Florida and the best heckle he’s ever gotten.

You grew up in South Florida; have you been to Sarasota?

[When I was first starting out] I traveled throughout Florida and played Sarasota a number of times, so I’m very familiar with the area. Of course, when the election was contested [in 2000], I used to joke that I was going around the country doing my apology tour—“Sorry about our state! We’re just doing our best to get things right.”

Do you have jokes that work in certain parts of the country and not in others?

Well, when I do the joke about "What’s with all the stupid people in New York?," it doesn’t work in New York. [Laughs] Just kidding!

I think television and the Internet have homogenized our country to a degree, but not completely. There are different [viewpoints] in different areas, but the jokes travel pretty well. I’ve recently been venturing into topics that are a departure from things I used to do, like jokes about gun control. I don’t go super far in that direction, but I like to touch on things. When I bring up that topic in certain cities, it definitely gets a different response than in others. But that’s what’s cool about our country.

Walk us through your creative process. How do you approach writing a joke?

I’ll see or read or experience something, and then my brain says, “Wow, that could be a bit or a joke.” Once you have that, you can apply a craft to it—choose some words, [create] a middle, a beginning and an end.

But some of the best writing takes place on stage, when you’re in the heat of the moment. I always think of those old movies, where someone runs into a newsroom, throws a piece of paper down on an anchor’s desk and says, "Hot off the press, read this now!" It’s sort of like that when you’re doing a joke on stage. You might have it pre-planned, but then the back of your brain runs up to the front of it and says, “Say this now!”

That’s part of the beauty of comedy. It can be altered and made better.

What’s the best heckle you’ve ever gotten?

Years ago, I was doing a show and I had a joke about airline travel, a joke about taking a Greyhound bus and a joke about rental cars, and I wasn’t wise enough to think through how I got into the jokes. So I said, “I flew into town!” and did the airline joke. Then later in the act, I said, “I took a Greyhound bus here,” and then even later I said, “I drove a rental car to get to this town.” And a guy in the back yelled, “That’s three modes of transportation!”

What a beautiful heckle. He nailed me.

Vanity Fair called you “the funniest stand-up alive”—that’s pretty cool. Was there a moment when you felt like you’d made it?

I don’t know if there was ever a moment where there was a line in the sand, like, yesterday I was not successful and now I am. I think everything’s been added in a cumulative way. My following has increased very gradually over the years.

On the flip side, got any stories from a night when you bombed?

Years ago, I was doing a show and there was a window open near the stage. I wasn’t doing well at all; I finished a joke and got nothing. And then, through the window, I heard a cricket. You know the saying, “I was so bad I heard crickets”? I literally heard crickets during my stand-up comedy show.

Who are some of your favorite up-and-coming comedians?

There’s a guy named Sebastian Maniscalco who avoids the stereotypical track—he’s Italian and he uses his cultural background to just try to figure things out in the world. Bill Burr is another guy who’s doing the same thing and has a very, very distinct point of view. And I think Maria Bamford is wonderful; she does these offbeat characters and becomes them during different moments in her act. The more unique someone is, the more into their act I am.

And I like comedy that comes from a nice place, too. I don’t care if it’s rough around the edges, I don’t care if someone’s “dirty” or “blue,” but I like there to be a niceness somewhere in there.

You once told fellow comedian Jim Gaffigan that you wouldn’t mind doing a TV show if the timing was right, but that it’s not your end goal. So what’s next for you?

Stand-up comedy is always the goal. But if I can occasionally do something off that track, then I’m open to it. I use the Jerry Seinfeld model—he always thought of himself as a stand-up comedian, even while he had his TV show, and knew he was going to go back to stand-up once the show was over.

That doesn’t mean I wouldn’t like to do a TV show, but [now] I can be much more judicious about the types of things I would entertain. I don’t want a show just for the sake of having a show; I’d want one that reflects my comedy and how I think as a comedian.

Plus, I want a million dollars an episode. That’s how I start every meeting. Maybe that’s what’s keeping me back. [Laughs]