Brian Regan on Clean Jokes, Letterman, Red Rocks and Top Five

Brian Regan is one of the very few comedians who's achieved an arena-headlining level of success on the appeal of his jokes alone. Regan's observations on everyday peccadilloes and his emphatic delivery have won him generations of fans, from Mormon elders to precocious young comedy nerds in training. Unlike many other standups with his level of fame, Regan also enjoys the widespread respect of his peers, both for his good-natured work ethic and keenly crafted observational jokes. He manages to sell out huge venues despite a comparatively low media profile, making his silver screen debut only last year, in Chris Rock's directorial debut Top Five. Over his decades-long career, Regan appeared on the Late Show with David Letterman 28 times before the venerated host retired earlier this year. Known for his clean material and energetic performances, Regan demonstrates that a comic can have mass appeal and integrity. In anticipation of his headlining gig at Red Rocks Amphitheater on Saturday, September 5, Westword caught up with Regan over to discuss the legacy of David Letterman, his reputation  among fellow comics and some of his most enduring bits.

Westword: Let’s talk about your new comedy special, which airs live on Comedy Central later in September.

Brian Regan: That’s correct.

Whose idea was it to do a live special?

Well, I think it was mine. I was talking to my manager a year ago, and we were figuring out the next place for me to record an hour. I wanted to think of something interesting and different to do, and I thought a live thing could be intriguing. So the suggestion was brought to Comedy Central, and they liked it, so we’re doing it. And the idea came from my goofy little brain. 

Do you have any fears about doing a live show?

A little bit. You know, I look at it this way: I’m doing a live show every time I do comedy. It’s just usually for smaller audiences. This will be a bigger audience. Are there some risks involved? Sure, but you gotta do these things in life. For me, it just makes things more exciting. I figure there’s about a 90 percent chance that everything will go the way I hope it goes, but there are no guarantees in life. It’s what makes life fun.

Is that the hour you’ll be doing at Red Rocks?

Uh, that’s a great question. Obviously, I’m working towards that Comedy Central special and I don’t have a lot of shows between now and then, so I’m really trying to tighten things up. Usually when I’m doing shows for my fans or whatever, I’m thrilled to just play around onstage, but at this one I’ll probably be zeroing in on the set that I need to do for the special.

You’ve been to Red Rocks before, right?

I did it once before, a couple of years ago. It’s amazing, man. I’d been there before but I’ve never seen a show there;  I’d checked out the venue during the day. But to perform there was just —it’s weird what goes through your brain in a situation like that: “How did I get to this place, where I’m actually performing on this stage!?” It was just a fantastic audience last time. I’ve always loved Denver, I used to perform quite often at the Comedy Works, which is one of the best clubs in the country. So I have a good following there, and we thought we’d be able to pull it off, and it seemed to work pretty well.

What’s it like to perform in an al fresco environment like that? I’ve heard that the laughs can kind of disappear into the night.

I think a lot of comedians don’t care for outdoor environments, but I like them. Years and years ago there was this thing —I think they called it “Comedy Day” — in San Francisco in a park, and it was a fun experience, but a lot of the comedians felt like the laughs just went upward, you know? I just try to make them laugh hard enough that I can still hear it outside. I like it. It’s different. I remember one time doing an outdoor show, and at the time I had this routine about the moon, and I looked up and saw the moon above me and I thought ,“That’s the biggest prop in the history of standup comedy!”

Do you get a lot of spare time in the cities you visit?

Not as much as I used to. It used to be, when I was performing at comedy clubs, you’d be in town all weekend and maybe a few nights beyond the weekend, so you’d get to experience the city a bit. Now that I’m doing the one-night deals — and, every travel situation is different — but sometimes you’re literally arriving in town that afternoon, taking a quick nap, doing the show and blowing out of town right afterwards. That’s one of the...I wouldn’t call it a downside, but it’s just one of those things that goes along with it. I think people have the idea that we get to explore these cities more than we actually do, which is unfortunately not the case.

You’ve made 28 appearances on The Late Show with Letterman. How did it feel to be a part of that legacy now that the show has wound down?

It meant everything to me. David Letterman is revered in the comedy world. He has the type of comedy that people who know comedy respect; he’s very subversive. He’s also a kind person. He could put somebody in their place if he thought that they were full of B.S., but if he liked somebody he was very gracious. To have somebody like that enjoy what you do just means everything. He’s not the most sociable person; I never hung out with him. I never flew kites with him in Central Park or anything, but I heard from people on his staff that he liked me. And he must’ve to have had me back so many times. And the things he said to me on-air always felt genuine. To feel like you’re included in such a big way in a comedy show that’s so revered by comedians was a huge honor.

You didn’t do any other talk-show appearances in that time slot. Now that Letterman has retired, do you consider yourself a free agent now, late night-wise?

Yeah, we’re trying to figure that out now. You know, I was fortunate to be in that Letterman camp, and now that he’s no longer on the air we don’t know what we’re going to do. I keep saying “we,” like I’ve got this whole giant team around me. “What are we gonna do, team?” I’m looking around an empty office right now. There’s nobody else in here. Anyway, I don’t know yet.

Where do you go to work out new material? Do you have favorite comedy clubs for drop-ins?

I pretty much work my stuff out in my regular shows. I like to create comedy — that sounded pretty lofty, like I’m some kind of painter. But anyway, I like to come up with stuff. So when I’m doing my regular shows I just try to figure out a place where I can squeeze it in there. I mean, you usually try to bookend the new stuff. You open with something strong, then you try the new thing and if that doesn’t work, then you finish with something strong. Audiences are cool. They’ll give you a few foul balls. You don’t want too many of those in a show that people are paying to see, but a handful can actually be good for the act. It’s good for audiences to see that this isn’t easy. If anything, it makes them respect the stuff that does work even more. It’s not easy coming up with bang joke, after bang joke, after bang joke. You want them to see behind the curtain a little bit.

So pretty much every time you do standup, it’s a full hour.

Yeah, except for a TV set or sometime like that. That’s a whole different animal. But if people are coming out to see my show, that’s usually gonna be an hour.

You’ve said before that a lot of your biggest breaks have come from other comedians — like Chris Rock casting you in Top Five, for example — while the media and industry have overlooked you, but is there something comforting about having a career built on the esteem of your fans and co-workers? If the industry never gives you anything, then they can’t arbitrarily take it away, right?

That’s true. I’m very honored to have a following among people out there. To have other comedians like what you do is just everything to me. It’s great. I’ve always kinda scratched my head at the fact, and when I say “the media,” I mean like a national level. The entertainment media and the networks out in L.A. just have a kind of blind eye towards what I do. I never completely understood why. But, like you say, they can never take away what I’ve built. I’m proud of the fact that I built it even though I certainly didn’t have any of their help!

How do you train your brain to write observational jokes? Do you have to constantly be on the lookout for everyday absurdity?

It’s weird. As far as the original inspiration for a joke —I still don’t know how that happens. It happens in your brain. You see or experience something, but you’re looking at it through a prism that other people don’t see through. It’s refracted in a comedic way. How that happens, I don’t know in terms of the original inspiration. But once you have the nucleus of a joke, then you can apply a craft to it. You put it into a form with a beginning, middle and an end, so you can try it onstage. But as far as just sitting down with a blank piece of paper and coming up with comedy, that’s just never worked for me. I’ve never been good at having someone point at me and telling me, “Hey, say something funny! Write a joke about the following topic!” I can’t do that. I only think of the things that just happen to pop up in my head. I can’t plan them.

Because your material is so approachable, I’d imagine that you’re among the first standups that people hear as a kid. I definitely remember your joke about saying “you, too” to ushers at movie theaters who won’t be enjoying the show, or getting off of an elevator on the wrong floor. Kids are always struggling to not look like idiots, so it was sort of comforting to have this mulleted adult talking about the same embarrassment.

I appreciate that, thank you.

Do you think it’s important that families can enjoy a comedian together?

Well, it’s nice to have fans of any age. One of the challenging things about working clean is that some people think that means I do a kiddie show. They hear the word “clean” and they think “Disney” — not that I have anything against Disney movies, I take my kids to see them. Even though my show is clean and a kid wouldn’t be offended by anything I said, I still want to be able tell jokes about having high cholesterol and signing mortgage documents, or foreign policy. I want to be able to talk about things that aren’t necessarily kid-oriented. I’ve always been troubled by the definition of “clean,” because I think it conjures up something that I’m not really all about.

I think some people conflate “clean comedy” with a lack of sophistication. I don’t think you’d be so respected by your fellow comedians if that were true, though; clearly you’re not just doing a kids’ show.

I think comedians respect the craft of comedy and they don’t care whether it’s clean or not. They just like somebody if they’re funny. That ‘s why I love having the support of other comedians. But when you throw that term out there into the general public, people misunderstand. “Clean” may be an accurate description of what I do, but it’s also incomplete, you know what I mean?

It’s reductive, to be sure.

Some family could come see me and expect me to be twisting up balloon animals onstage. Now I’m worried that some guy who twists balloon animals is going to read this and go, “Wait, why does he have to kick me in the ribs to make his point?”

Well, it looks like you’ve offended your first person.

I’m going to have a bunch of angry balloon-animal twisters protesting in front of my next show!

They’re a powerful subculture, and they’re very active on social media. You’re going down, Regan.

I’ve awakened the sleeping beast!

Brian Regan will be at Red Rocks Amphitheatre on Saturday, September 5. Doors open at 6:30 p.m. for the 8 p.m. show. Admission runs between $39.50 and $65, depending upon seating section; tickets are available from the Red Rocks website.

Follow Byron Graham on twitter @ByronFG for more mildly amusing sequences of words.

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Byron Graham is a writer, comedian and gentleman thief from Denver. Co-host of Designated Drunkard: A Comedy Drinking Game, the deathless Lion's Lair open mic and the Mutiny Book Club podcast, Byron also writes about comedy for Westword. He cannot abide cowardice, and he's never been defeated in an open duel.
Contact: Byron Graham