Ahead of the show, we talked with Regan about getting started with Carson, doing some acting, keeping it clean, and his funny family.
In the ’90s, you appeared on Johnny Carson and David Letterman. Today there isn’t really a “Carson” or “Letterman,” those rare shows that everybody watches and establishes that you’ve arrived as a comedian. If you were starting today, without those destination points but with many more opportunities to get your material to the public on your terms, would it be easier or harder? How would you go about building a career?
If I was just now starting my stand-up comedy career, I’m not sure I’d know what to do. Years ago, I took Greyhound buses from one city to the other to audition at comedy clubs. If someone on one of those bus rides told me I should start a “podcast,” I would’ve gotten up and moved.
Many comedians land a television or movie role early on and ride that notoriety for several years. You’ve built your career differently, with steady writing and touring and being known as a stand-up comedian first and foremost. How has that affected your longevity, and has that made maintaining your success easier or more difficult?
I take pride in knowing that if someone comes to see my show, they are doing so simply because of my stand-up comedy. They couldn’t know me from anything else. Well, I guess some people might be coming out because they remember my Pilot Pen commercial from 1993.
You’ve also done a fair amount of acting, such as your regular role on the acclaimed series “Loudermilk.” Is that something you’d like to do more regularly, and would that require scaling back your stand-up schedule?
I’m glad Peter Farrelly cast me in Loudermilk. It meant a lot to me to show some acting chops. Chris Rock was also kind enough to give me a small role in his movie “Top Five.” If another acting opportunity came my way, I’d be very open to pursuing it. Maybe one day I will be lucky enough to do an underarm deodorant commercial.
You’re known for your clever material without being vulgar or dirty. Do you intentionally write that way, or does it just come naturally?
When I first started doing comedy, I wasn’t completely clean. In the early years, I guess about 5% of my act was “dirty.” I dropped that five percent because it didn’t feel natural to me. Right after I dropped that stuff, people would heckle, “Where’s the other five percent!?”
At your level, you probably aren’t hitting open mics on off nights. Is there a place you go to work out new material, or do you just fit it into your set?
I always try new stuff by just sticking into my regular shows. If something new doesn’t work, that’s fine. Audiences are cool with foul balls. Wouldn’t it be weird at a baseball game, if everyone left after the first foul ball?
Your brother, Dennis, has also had a successful stand-up career. Do you ever bounce ideas off each other, or offer up tags or advice when hearing the other’s material?
Dennis and I like each other’s comedy quite a bit. Occasionally, one of us might offer the other a small piece of advice. For example, once I got off stage and Dennis said to me, “Try not to be so stupid.”
You come from a family of eight children. Which of your siblings (who isn’t already doing stand-up) is the funniest, and why?
All my brothers and sisters are funny. I think my oldest brother, Mike, is hysterical. If you asked him a yes or no question, it wouldn’t matter if he answered yes or no, his answer would be funny.
As someone who uses observational comedy, what you “observe” has probably changed over the decades as you move through different stages of life. Does that change how you find funny things, or what things you find funny? How is your process different than when it was when you were starting out?
I like to do “observational” comedy. But I also like to throw some absurd stuff in there as well.
You sell a number of your pre-Netflix specials on your website, brianregan.com. We assume that means you own a lot of your content. How important is it for comedians (and perhaps artists in general) to maintain control of the material they create, and what would you say to newer comedians who might have to choose between owning their content and gaining access to a platform that would improve their visibility?
I wish I knew more about the business side of things, but I try to be as smart as I can be when it comes to that stuff. Usually after I make a business decision, my brother Dennis will say to me, “Try not to be so stupid.”
This article appears in May 4-10, 2023.