Brian Regan has been making audiences laugh for decades thanks to his side-splittingly funny stand-up act (in fact, Vanity Fair has called him "the funniest stand-up alive"). In addition to his touring act, he also appeared on the Late Show with David Letterman 28 times—more than any comic since the show moved to CBS in 1993—and has been seen on shows like Jerry Seinfeld's Comedians in Cars Getting Coffee and The Tonight Show with Jimmy Fallon. Reagan also recently inked a two-special deal with Netflix, joining the likes of Dave Chappelle, Jerry Seinfeld and Chris Rock. The first special, the very funny Nunchucks and Flamethrowers, began streaming on Nov. 21, 2017; the second will debut in 2019. 

Regan will appear at the Van Wezel on Thursday, Feb. 8, at 7:30 p.m.; we talked to him in advance of the show about how he crafts a good joke, his thoughts on the intersection of comedy and politics, and what audiences can expect from his current tour.

We spoke about two years ago, when you were on tour and the Van Wezel was one of your stops. Do you have any lingering memories of Sarasota?

Sarasota is the most beautiful place on earth. The people of Sarasota are the best people in the world.

How did you get your start in comedy?

I thought I was going to be an accountant, but after a month or two of accounting classes, I would go back to my dorm, look in the mirror [and say to myself], "Is this exciting to you?" So I switched majors, to communications and theater arts, and I took acting classes and speech classes and TV production classes. I still got horrible grades, but I loved it while I was getting F's.  

Did you always know you were funny?

I used to like making my friends and classmates laugh. What's weird is that in eighth grade, a committee of fellow students made a memory book for our class and wrote down everyone's name and what occupation they thought [the person] would go into. For me, they wrote "comedian and showman." My classmates knew before I did! 

Who gave you the best advice when you were starting out?

There was a guy named John Fox who passed away a few years ago. He was very dirty, but he knew how to command a stage, and it was fun watching him knock it out of the park. Every time you perform, you perform with other comedians, so it's like going to school. You never want to take material, but you can learn other things, like how to work the stage, do transitions, things like that.

John Fox also taught me something that seems so trivial, but it was important at the time. When I was new and green, the laughs were inconsistent, and I used to go on stage with a bottle of beer, put it on a stool and do my act. So one night, after a so-so show, John said, "Hey, can I talk to you? When you're doing a joke that doesn't get a laugh, you walk over and take a sip of beer. It's torture because no one is laughing. The only time you should take a sip is during a laugh. Long story short: earn your sips." [Laughs] So I learned how to earn my sips—now I won't take a drink unless there's a laugh happening.

What's your creative process like?

I open up a piece of Bazooka bubble gum, look at the funny cartoon in the wrapper, write that down and pretend like I came up with it. I have 100 pieces of gum, so that gives me 100 jokes, and that's my new routine. [Laughs] No, I just go through my day the way I normally would, and every once in a while things pop out in a weird way. You know those three-dimensional posters that you have to look at for awhile to see what's in them? I think jokes are like that—every so often, you see something you've looked at many times in a way that's unusual, and there's a joke there. I test it out as I'm touring and it gets refined from there.

Tell us about Loudermilk, your new TV show.

Peter Farrelly is the director and co-creator, and the show's title is the main character's last name, who's played by Ron Livingston. He's a no-B.S. kind of guy who runs a small group discussion for people recovering from substance abuse. I play one of those recovering people.  You wouldn't call it a situation comedy—it's a funny, serious show. It was a lot of fun to work on, and I believe we just got the green light to make season two. I'm very proud of it.

Who's making you laugh right now?

I've been watching old Norm MacDonald clips. He's got an interesting, funny way about him, and I've been watching him do his jokes on talk shows or panel shows and getting a kick out of it. Panel shows are different animals from stand-up—doing them is a skill in and of itself—and I really like watching what he does in that situation.

When you were here last, you were trying out some political material, which also made its way into your latest Netflix special—that's a bit of a departure for you. What's been the audience reaction? I'm sure you have fans on both sides of the aisle.

I think they like it. I try to be cagey and do the kind of material that both sides can laugh at. In fact, I want both sides to think I'm on their side. I try to walk a tightrope, where I can touch on some [topics] that might be challenging but where both sides can have a laugh. There are comedians who do like to take sides, and everyone should do what they want to do on stage. But I only have five to 10 minutes of politics; it's not worth it to me to cut my audience in half.

Since the election, it does seem like comedians are sometimes better at covering political news stories than even the regular news outlets. Why do you think that is?

Well, even if we're not doing a political joke, comedians try to get to the laugh as quickly as possible. Brevity is important, so if a comedian happens to talk about politics, they include brevity in that message, and say it in a tight, concise way that also happens to be funny. And when you laugh at something, you internalize it as a truth. Laughter is powerful. 

What can people attending your show at the Van Wezel expect this time?

I'm starting to move away from the special that just came out, because I'm doing another one for Netflix in about a year—I'm repealing and replacing this act. It's fun for me; it's like taking a big piece of clay and trying to form it into something new. I'd like to think audiences have been enjoying it.

This interview has been condensed and edited for clarity. To get tickets to Regan's Van Wezel performance on February 8, click here.