Brian Regan is always on the lookout. That’s what 30-plus years of standup comedy will do. Of course, the craft–and ultimately art–of his style of humor is the skill to convey the personal and have it hit a universal audience. He’s succeed greatly on both fronts, blending personal insight and a kind of fearless sarcasm, and even silliness, which have earned him a devoted audience spanning generations. Some of that is surely due to his riffs on our shared experiences of childhood, but his stabs at the pedestrian monotony and frustration of the human experience make his material entirely relatable. While Regan works “clean,” (an omission to which he seems indifferent) a lack of vulgarity only increases his humor and abilities, since he has no fall-back of firing off F-bombs from a foxhole to try to shake up the audience.

The use of the descriptor “organic” has become increasingly inorganic. Yet Regan’s rise from the ’80s standup comedy boom progressed in a seemingly natural way. He was a favorite on Late Show With David Letterman, ultimately appearing a staggering 28 times, more than any other comedian on that show’s history. Aired in 2015, Brian Regan: Live from Radio City Music Hall, was the first live broadcast of a standup special in Comedy Central’s history. Along with his loyal fanbase, Regan is admired by notable fellow comics—Bill Burr, Marc Maron, Patton Oswalt, Chris Rock and Jerry Seinfeld are just a few among many who sing his praises and call him their personal favorite.

Regan keeps too busy to let this unilateral success go to his head. He’s a road veteran, still performing up to 100 shows a year; Netflix is soon releasing two new Regan comedy specials.

In conversation, Regan is erudite, humble and–naturally–funny, discussing his career and the ongoing development of his craft. Here are some highlights of our conversation.

Folio Weekly: So you’re releasing not one, but two, specials on Netflix. Both in the same year?
Brian Regan: It’s kind of confusing. I have a deal with Netflix for two separate one-hour specials. The first one will be coming out in November; I’ve already shot that. And the next one will be in 2019.

How much pressure is that? I think it’d be one thing if you’re riffing on stuff that’s not being filmed … but is there greater pressure in filming two shows like that, which could easily be watched by millions of people?
It’s a challenge. I don’t go as far as to say it’s pressure because I like the challenge. You know, I wouldn’t have accepted the opportunity if I didn’t feel like I could do it. I’ve done this so long that I feel like two years is enough time for me to really have some strong-enough material to create a new hour. But it’s not easy. It’s really a lot of work–but I enjoy it. I enjoy that process of trying to make it better and better, night after night.

Regarding that process: Are you among those writers who lock themselves in a room for eight hours until they’ve written at least one good joke–or are you more flexible or fluid?
I’m not that good at sitting down and forcing myself to come up with stuff. I just kind of go through my day the way I’d normally go through my day and every once and a while, things jump up and down. You know, I don’t know how that works–I’ll see something, hear something or experience something–and go, “Hey, that good be a bit.” And once you have the nucleus, then you can apply a “craft” to it and try to convey the words to make it tight as possible; and it might or might not work. Sometimes you can tell it onstage and get literally nothing. [Laughs.] Sometimes it’ll kill right away, but usually if there’s something there, they’ll laugh; but it’s not tight yet. So then there’s a process you have to go through where you need to figure out better words and a better way of conveying it.

So it sounds like the keys to this are brevity and clarity. If you tell a story that’s too long, people will start staring at the ceiling or readjusting their watchbands.
[Laughs.] Well, that’s part of it. But I also feel like you can make it too tight also where you suck the humanity out of it. [Laughs.] You know what I mean? So you’ve gotta be careful–at least it’s my perspective and it depends on the comedy you do–you don’t want to take so many words out that it sounds like there’s no longer a person onstage just talking with you. It’s a fine line. You don’t want information that’s unnecessary for the joke but you also don’t want so little information that you suck the personality out of the joke.

Sure. Like: “There was a guy who did something, then he saw something and then he fell down. Thank you and good night.” Like a Mad Lib: “You fill in the words, folks. Shout out a noun.”
[Laughs.] I wish I was taping that. That’d be my next joke!

Take it! I also have a killer 45 seconds on “How do you throw away a trash can?” Seems like you’re of the breed where you, or at least the characterizations, are the punchline. I mean, unless someone is a total narcissist, psychopath or Donald Trump, self-deprecating humor is a never-ending wellspring of ideas. Do you agree?
Yes. But similar to the previous answer where a joke can be too tight, I feel the same way about self-deprecation. As the guy onstage the audience is listening to, I also have to be self-aware enough that I’m making these observations. If I’m just a goofball, then it’s buffoonery. You know what I mean? So it has to be a person who can make fun of himself; but I’m also trying to let the audience know I’m wise enough and sharp enough to make observations about the world that are hopefully sharp–occasionally–and within that, I can also make fun of myself. But if you take away the sharpness, you lose the overall message.

Regarding performing, in your interview on [podcast] You Made it Weird with Pete Holmes and a [Sept. 28, 2015] Vanity Fair piece, you talk about “playing the audience” as this “instrument” or “big blob of humanity.” When did you realize that this perception or approach was what worked best for you?
Well, it’s easier for me to try to do things I think are funny than it is for me to try to do things other people think are funny. [Laughs.] I’m not qualified to know what people … in the audience think is funny. That’s too daunting a task. [Laughs.] But I can share with them what I think is funny and if they agree? Great. Then I have an act and then I have a career. And I’m fortunate they often agree. They agree enough that I can do this for a living. And so, because of that, I’m not thinking, “What would that guy laugh at? What would she over there laugh at?” I’m really just trying to say what I would laugh at if I was out there. And then the audience just becomes this thing. I’m trying to make this entity laugh. And you can call it whatever you want: … an instrument, … a blob, … a thing … But it’s easier for me as a comedian to get as much volume and noise out of this writhing mass I can. [Laughs.]

I think there are some strong parallels between standup comedians and musicians; surely in the sense of a musician improvising and playing a few “off” notes just trying to take the music somewhere new. I guess I’m wondering if you ever feel as if you are “good” every night if you’re not in some way exploring the material?

You know, that’s a good question and that’s something that I’m very cognizant of. I’ve used the analogy of thinking of my act as an accordion. You talked earlier about trying to keep jokes as tight as possible?  Well, that’s one goal. So that’s squeezing the accordion together. But another goal is pulling it apart and try to fit as many things in there as you can. And both of those are valid goals. Sometimes with one joke you’re in “tightening” mode and then with the next joke you’re in “widening-this-baby-out” mode; to see if there’s more stuff there that you can explore. And that’s what’s fun about the process-sometimes a whole show can be a “tightening” kind of show or some show is a “widening” kind of show…sometimes it’s a joke-by-joke thing. And I get to choose while I’m onstage what direction I want to go. Clearly when you’re doing a TV taping, like a Letterman or a Fallon, well, that’s going to be a tighter version. You’re gonna have it lean and mean. [Laughs] But when you’re performing in front of an audience, sometimes you want to play around with the moment and really see what else is in there.

Observational comedy seems like it needs to somehow always be based on shared experiences; finding something mundane with a perspective and then blowing it up for people to laugh at it. I mean, you can’t walk out onstage and say, “Hey! I just ate a baby seal with the King of Belgium!”

[Laughs.] That might be a hard one to sell.

But you know what I mean? It seems like you might need to talk about the pain in the ass of needing to go to Wal-Mart at midnight, something that everyone does. How do you think you’ve found the key or core elements of experiences that audiences seem to identify with?

I, uh, don’t know. I still don’t know how I do it. And I’m not trying to be flippant. That’s part of the joy-in that occasionally you can figure that out, and occasionally you can’t. Sometimes a joke is about a shared experience, where you might do it in an autobiographical way but you want the audience to say, “Oh, I see what he’s talking about. I’ve seen that and maybe I’ve never noticed it in the way he’s presenting it-but I know what he’s talking about.” So there’s that shared experience aspect. But you also have jokes where you’re trying to educate. You know, where you say, “This is what we usually do-but maybe we should do this.” Every joke has a different agenda. And it’s interesting what you’re asking because I’ve watched comedians where you see them do a bit, where they’re going for a shared experience kind-of-laugh, and I’m in the back going, “I don’t agree with this experience!” [Laughs.] I don’t agree with how he or she I feeling. And the audience isn’t either. That bit isn’t working-not because they aren’t good comedians-but because they’re riffing on a shared experience that the audience isn’t necessarily agreeing with.

Like, “I buried my dog in a lightning storm! Isn’t that the worst?”

Right. “Well, uh, hey! I lost a pet, too.”

You’re now such a well-known comedian that I’m wondering if you’ve fallen to victim to, “The Carlos Mencia Effect,” where you’ve caught other comedians stealing your jokes?

[Pauses.] I’ve had it happen. Yeah. I don’t want to sound like I’m patting myself on the back but I’m successful enough where people know my material. So if somebody even tried to take it, it isn’t like I’m an obscure guy that somebody saw in Ohio, where you could probably get away with stealing the bit. If somebody steals a bit of mine, another comedian is going to say, “That’s Brian Regan’s bit.” You know what I mean? So I’m fortunate in that my stuff is kind of “out there” in a big way where it would be more of a challenge for someone to take it. But I’ve had it happen and sometimes the best approach is to just keep cranking out new stuff to stay ahead of it. You know? There’s a big wave coming behind you. Just stay in front of it.

I guess if some West Virginia coal miner stole your joke and is telling it during the lunch break 100 feet deep into the earth, it’s like: “You know what? Let him have it.”

That’s right. Those coal miners could probably use a laugh.

You have a lot of notable peers that sing your praises. Does that kind of admiration ever add a level of being self-conscious when you’re working?

No. I’m very flattered by it and it means the world to me that people of that stature seem to like what I do. But I’d like to think that part of what they like is that I try to keep my nose to the grindstone and have it be about the comedy, you know? I’m not trying to do stuff to impress comedians. I’m just trying to come up with stuff that I think is funny and make it as good as possible. If, along the way, comedians like it or audiences like it? Well, wow, that’s fantastic. But I don’t put the cart before the horse.