PHOTO PROVIDED Stand-up comedian Brian Regan will perform at 7:30 p.m. on Sunday at the Community Arts Center.

When he was an up-and-coming comedian, Brian Regan used to walk around with a piece of paper and pen everywhere he went, making sure to jot down any funny observation or situation that might make for good material in his stand-up routine. Decades later, not too much has changed. Sure, Regan’s notepad is now on his phone, but he’s still always looking for the next bit of inspiration to jump out at him.

“I walk around in life with a red wagon that I pull behind me,” Regan said playfully. “If I see something funny, I put it in the wagon.”

Regan’s unique point of view, gift for self-deprecation, and goofball demeanor have made him a master of his craft over the last 40-plus years. Beloved by fans and fellow comedians alike, Regan’s career has seen him perform for packed crowds in some of the world’s most renowned venues and put out eight comedy specials. His two most recent efforts — “Nunchucks and Flamethrowers” (2017) and “On the Rocks” (2021) — can both be streamed on Netflix, along with the TV series “Loudermilk,” on which he co-stars.

Area stand-up fans will get a chance to experience Regan’s legendary act for themselves this weekend, when he performs at 7:30 p.m. on Sunday at the Community Arts Center, 220 West Fourth Street.

In a Q&A, Regan recently spoke with the Sun-Gazette about his enduring career, being labeled a “clean” comedian, performing for tough crowds, and much more.

SG: When did you first realize that you were good at making people laugh?

Regan: I used to love making my dad laugh. My dad had a wonderful sense of humor and if you got him laughing, he would laugh in a way that was like — I had never seen anybody who would laugh like my dad. He would literally make physical gyrations and stuff. It was a very, very pleasing experience to make my dad laugh, so those are probably my oldest memories of making someone laugh.

SG: When did you perform comedy for the first time and how did it go?

Regan: There are a number of firsts, if you will. It’s kind of hard to say. I used to MC college activities. Like, one time they asked me to host a gameshow, and I was the MC of a gameshow. I was being funny, but I wasn’t doing stand-up per se. The first time I remember saying, “Hey, I’m going to do stand-up comedy,” it didn’t go well. It was in college and I did it at the college bar, and a bunch of friends and teachers and stuff came out. It’s a different animal. When you say you are going to be funny, it’s different than just being on a microphone and happening to be funny. I remember learning the difference that night.

SG: Were you immediately comfortable on stage or is that something that took time?

Regan: It took me a while to get comfortable on stage. The comedy club where I started was in Fort Lauderdale, Florida, and I remember being very nervous and scared the first time I went up. Then I was nervous every time I went on stage for a long time. I remember being nine months into it and standing next to the stage while I was being introduced and thinking to myself, “This feeling has me petrified. Why do I do this? I don’t have to do this. All I have to do is walk out of this place and get in a car and go home. But obviously there is something in there that I’m looking for.”

SG: At what point did you start thinking that you could make a career out of comedy?

Regan: The club where I started, I worked there as a dishwasher and a busboy when I was trying to get into comedy. They would let me go on stage and do time. Little by little, I got more comfortable. I was probably about a year in of doing it almost every night when I started thinking, “Alright, maybe. Maybe this could be something I do for the rest of my life.”

SG: What do you think is the most rewarding aspect of doing stand-up for a living?

Regan: It’s fun. I am fortunate enough to do something that I think is fun for a living. I feel like I have the ultimate scam going, because now I enjoy doing it so much that I would pay to do it. Like, the show is over and I feel like I should sit down and give somebody some money; but they give me money. I’m like, “Somebody is a bad negotiator because I would pay to do this and somehow they give me the check.”

SG: What does it feel like to hear one of your jokes get a big pop from the audience?

Regan: The feeling is always strong. To think of something in your brain and say it in front of people and have them laugh, it means you’re communicating and you are on the same wavelength. It’s a cool experience. One thing I like about comedy is that people rarely fake laugh. People will applaud when they don’t like things, but people don’t laugh when they don’t think it’s funny. So, when you get somebody laughing, you know that you are having an honest interaction.

SG: Do you think being labeled a “clean” comedian has opened you up to more opportunities that wouldn’t have been there otherwise, or presented you with more challenges?

Regan: It’s a double-edged sword. I don’t work the way I do to try to draw audiences; I do it because I enjoy it. I don’t like to promo the fact that I’m clean because I don’t want people to say, “Oh, I don’t want to go see some super wholesome comedian.” Whereas, if they came and saw me and didn’t even think about whether or not I was clean, they might have a blast and think that I’m funny. But once you put that word on there, there is a connotation associated with the word “clean.” That’s why I never use it on my promo materials. In fact, I showed up to a comedy club one time and they had my name up on the marquee and it said “good, clean fun” under it, and I said, “You have to take that down immediately.” They said, “Why?” I told them, “That’s probably turning away more people than you’re bringing in.” It’s like, just say that I’m funny. Don’t say that I’m “clean” funny.

I use this example sometimes: The Beatles are clean — all of their music is clean. But if you were only to promo them as “clean music” then people would say, “I don’t want to see this.” But if you went and saw them you would say, “Wow, these guys are pretty damn good.”

SG: Can you remember the last time you actually bombed on stage?

Regan: It was not that long ago. I was in a city — Pittsburgh, I think — and I did my show and it went really well, and we found out there was a bar with an open mic night. So, we go to this bar that has a microphone over in the corner, and people were talking and drinking, and I wanted to do a set. So, I got on stage, and I tried to relive what it’s like to perform for crowds that aren’t so great, and I absolutely bombed. It was actually kind of a fun experience. It was like, “Wow, nobody is amused by this.” It was only a few weeks ago.

SG: Can you get a feel for how good a crowd is going to be before you get on stage?

Regan: It’s usually just one other performer and then me, and the other performer is the one who introduces me. So, I get to see how the audience is laughing at the other comedian to get a feel for it. Sometimes it doesn’t exactly translate and sometimes it does. Sometimes the crowd is great for the opener and they’re also great for me, and sometimes they’re not biting on the opener that much. But I try not to get a negative feeling before I hit the stage, because sometimes they’ll turn.

SG: Do comedians enjoy the challenge of taking on a tough crowd?

Regan: I’m sure there are comedians who have that feeling like, “I’m the guy that can turn this around.” But then there are also comedians that would rather walk on stage for a crowd that seems like a pretty good crowd — I mean, that’s my preference.

That place that I bombed, I remember thinking, “This is a challenge.” Because there were other comedians that had already been on stage that were getting nothing. I thought, “I’ve got some skills at this, let me see if I can turn this crowd around.” I wasn’t able to.

SG: After you get the inspiration for a joke, how do you go about writing it?

Regan: You get your initial idea and then you put some scaffolding around it, and you come up with a beginning, middle and an end. Then, you try it on stage, and when you are on stage sometimes you are finessing it while you are up there saying it, based on the reaction you’re getting.

SG: Where in your set do you like to stick your newest material?

Regan: I try to stick it in the middle and bookend it. I usually try to hit the stage with a joke that will get the crowd going. Then, once I have them, I’ll try to slip some new stuff in. You try to bookend it with something strong before it and something strong after it, and if it doesn’t work then it’ll be okay. Crowds will give you a foul ball; they’re okay with foul balls. But if you hit too many of them, they start losing interest.

SG: How is comedy different for up-and-coming comedians today compared to when you were first starting out?

Regan: If I were young and trying to start right now, I don’t know if I would ever be able to negotiate my way through how you have to do it today. When I started, comedy clubs were just starting to open around the country and most of them had open mic nights. So, I knew how you were supposed to try to get into comedy when I first started. Now, it’s so different, and I don’t know if it’s harder or not. I wouldn’t want to start in today’s world.

SG: Other than being funny, what are some qualities that all the best comedians have in common?

Regan: We are all incredibly handsome. Sometimes I’ll forget how handsome I am, and I’ll walk by a mirror and go, “Whoa, maybe that’s what the crowd is into.”

One of the things that we all have in common is that strong desire within us to make this happen. Because there are a lot of bad experiences along the way. You are going to have a lot of bad shows when you start. If you don’t have the tenacity and the fire within you to work your way through the rough nights, then you aren’t gonna make it. There’s a comradery between us, because we all know that we have that willingness to go through the experiences you have to go through to become good at it.