Conquering Comedy: A Sitdown with Brian Regan

Brian Regan is conquering the game of comedy — and he’s playing it fair and square.

With a career spanning stand-up, Netflix, and everything in between, Brian Regan is a seasoned entertainer. He has been called “an absolute master” by Bill Burr and “the best stand-up working today” by Patton Oswalt. The comedy veteran tours nearly 100 cities per year.

Regan didn’t always have comedic aspirations. He was on track to become an accountant before a change of heart permanently altered the trajectory of his career. “I realized that my eyes were rolling into the back of my head. I thought, ‘Is this what I’m going to do with the one life I get?’” he told the UCSD Guardian.

Since then, Regan has accumulated an impressive set of accolades and boasts an expansive repertoire. Regan has performed at Carnegie Hall, been a guest on Jerry Seinfeld’s “Comedians in Cars Getting Coffee,” and performed stand-up on “The Late Show with David Letterman” a record 28 times. His last special, “Brian Regan: Live from Radio City Musical Hall,” was Comedy Central’s first live broadcast of a stand-up special.

Regan’s talents recently caught the eye of Peter Farrelly (of “Dumb and Dumber” fame), who cast him in a feature role in his new show, “Loudermilk,” after seeing him perform stand-up. The show premiered on Oct. 17 on The Audience Network.

With the advent of online streaming, stand-up comedy has found a new platform. Streaming services like Netflix have become host to a slew of comedy specials, including Regan’s own. When asked whether the virtual viewing experience could parallel live performance, Regan spoke candidly: “I think live is always best,” he said. “It still translates, but it’s just not quite as strong as being there in the moment.”

To Regan, comedic prowess is the product of an innate sense of humor and distinctive individuality. “I think the more unique someone is in their persona and their style and their humor, the closer they get to being great. You have to have your own comedic message that comes across.” Regan cited some of his inspirations as examples, including Steven Wright, Richard Pryor and George Carlin. Beyond this, however, he recognizes the ineffability of comedic ingenuity. “Part of it is intangible. It’s hard to know — that’s what’s fascinating about it.”

As for Regan’s own comedic style, the quick-witted entertainer had some lofty sentiments. “It’s Kierkegaardian with Machiavellian undertones,” he quipped. Regan tries to create a hybrid technique, incorporating elements of situational, personal, and absurdist comedy. “There are certain terms people throw on comedy. One is observational — that’s a pretty wide net. I do that. But I also talk about personal experiences like going to the emergency room and things like that.” Regan’s comedy is branded as “clean,” but he resents the restrictive nature of this kind of label. “It creates a connotation of the comedy that is not in sync with what I think about the comedy. If it happens to be clean, great, but it’s about being funny.”

Regan recently signed a two-special deal with Netflix, joining the ranks of Chris Rock, Dave Chappelle, and Jerry Seinfeld — all of whom hold multi-deal contracts with the company. Regan’s first special, “Nunchucks and Flamethrowers,” comes out Nov. 21.

Regan also holds shares in another rarity: He may be one of the few people able to claim witness to George Carlin — one of his primary inspirations — bombing. Regan recounted how a theater where he was performing in Atlantic City allowed him and his fellow comedians to sneak in to watch George Carlin. The legendary comedian faced an unresponsive audience during an episode of comedic experimentation. “And I remember some guy getting up from his chair and walking straight past me and saying, ‘This guy don’t know nothing about comedy.’ It was sort of surreal, because I don’t think there’s a man on Earth who knows more about comedy,” Regan laughed. Regan pocketed the performance as a learning experience. “What’s he going to do? How’s he going to handle it? You’re learning by watching,” he explained.

Throughout the years, Regan has managed to bypass weariness and maintain a steady devotion to a craft that can be infamously cruel to those who practice it. “It’s impossible to be bulletproof. It’s just the nature of the beast,” he remarked. “There were a couple of times, not a lot, but a couple when I was not sure if it was going to work out. When you have a handful of bad shows you start going, ‘Do I know how to do this?’ You have to muscle your way through those moments, and I’m glad I did.”

Regan’s commitment to the work itself has fostered his career’s forward motion and allowed him to circumvent monotony in his routines. His material maintains relevance through continual revision. “I’m constantly changing what I’m talking about. I like to keep adding material,” Regan said.

For Regan, comedy is an opportunity to hold himself and those around him accountable. “A recurring theme in my jokes is just wanting everyone to be fair,” he said. Observed instances of injustice — whether they be extensions of stupidity or malice — are common subjects of Regan’s routines. “I like to poke a stick at it with my comedy,” he explained. Regan is not exempt from his own scrutiny. “I also talk about my own insecurities,” he added. His stand-up offers him the chance to examine his failures and take swings at his shortcomings. “When I don’t feel like I’m stepping up to the plate socially, I like to bring that to light comedically.”

Aside from being an exercise of liability, Regan hopes that his comedy will instill a sense of comfort in his audiences. “Obviously, I hope they laugh. Beyond that, I’d like them to think, ‘This guy seems like a pretty decent guy.’ I’d like for people to feel good about the world in which we live,” Regan explained. “At the end of the day, life is grand.”

Image Courtesy of Brian Regan