Chris Fleming on His HBO Special and Why Stand-Up Is ‘Embarrassing’

Chris Fleming would like to make one thing abundantly clear — he is not weird. 

“I’m very normal,” the comedian says, laughing over Zoom, in between large sips of a passionfruit green tea boba. “Maybe I am insane, because I don’t think I’m insane. But I do not see my work as weird. I like to keep things surprising and I like to surprise myself in my writing. That’s how I would view it: as a surprise party.” 

Surprise isn’t just a driving concept for Fleming. It imbues every aspect of his comedy, from the sharp three-point-turn style of his jokes to his frenetic presence onstage. At 39, Fleming has spent the better part of a decade slowly building a reputation in comedy circles for his absurdist takes on modern life and whip-smart observations about generational divides in the digital age. (The comic is famously nonchalant about gender and uses any pronouns.) Over six feet tall and skinny, with a mass of reddish curls, Fleming leaps and bounds across stage while delivering riffs on the bitmoji skills of baby boomers, ballads dedicated to deceased chain craft store Joann’s Fabrics, and Celine Dion’s gamer sons. 

Fleming is beloved by some of the biggest names in comedy — people like Conan O’Brien, Taylor Tomlinson, JB Smoove, and Caleb Hearon have all praised his signature brand of chaos comedy.  His 2015 YouTube short, “Company Is Coming,” where his character Gayle prepares her house for guests by psychologically terrorizing her family in a frenzy, has maintained meme status for so long that people still stop him at the airport over it. Now, with a new special, Chris Fleming: Live at the Palace, out now on HBO, Fleming is right on the edge of crossing over from underrated to downright popular. Yet he’s still too self-conscious to tell people what he does for work. 

“It’s an embarrassing job,” Fleming tells Rolling Stone. “[My comedy] is just like, ‘Hear me out.’ It’s too frantic to describe. I had a locksmith who I made the mistake of telling I was a comedian. And then he was watching my clips on his phone silently for the entirety of trying to fix my locks — which is tough.” 

Filmed at Chicago’s Cadillac Palace Theatre, Live at the Palace takes the underground nature of Fleming’s work and puts it on the main stage. There’s no thematic throughline. In fact, many times in the show, it feels like Fleming is just hearing his own material for the first time. Sometimes he pauses in the middle of his act, noting punchlines that the audience doesn’t laugh at and redoing the joke with a pointed aim; other times he abandons a tangent altogether to point out an audience member’s laugh. The end result is a charming and surprisingly intimate look into Fleming’s stream of consciousness, with some of his biggest insecurities around career, gender, and audience goodwill on display, all wrapped in the physical silliness of an inflatable tube man at a used car dealership.

Much of Fleming’s delightful frivolity can be seen in their mishmashed resume. After graduating from Skidmore College in Sarasota Springs, New York, with a degree in theater — and a close call with a minor in dance — Fleming struggled through what he calls a “dark abyss” of postgraduate life. He worked a day job as a substitute teacher for a kindergarten class. (“They would just chase me around, and I’d have to just run. I would be running as fast as I could the entire time. I had no control and oh, my God, my skin was horrible.”) At a local open mic hour in Boston, he was scouted by an agent, who convinced him to move to Los Angeles. He moved. She became a chef, leaving Fleming without any representation in a new city. 

But Fleming created their own big break with a YouTube series called Gayle, centered on the exploits of a furious, vaguely New England-accented mom. It became an internet classic, sparking almost a full decade of memes based on that singular scene where Gayle preps for company. “I want this place looking like Disney on Ice in one minute!” Fleming’s character screams, as she darts around the house carrying cleaning supplies. “If you haven’t made your bed, throw it away. It’s too late to make it now. Get rid of the couches. We can’t let people know we SIT!”

Though Fleming’s career took off with Gayle, he has no desire to incorporate the character into his stand-up. He has an almost pathological aversion to doing the same thing twice, and doesn’t mind taking his time between projects to make sure each one feels fresh and original. Case in point: Live at the Palace is Fleming’s first TV special in almost three years. The last one, Hell, which aired on Peacock, is an anxiety-inducing ride through a Great American Songbook reinvented entirely by Fleming’s stress dreams. The venue is small, the jokes often directly referencing Fleming’s longstanding feelings of displacement and discomfort. And the material takes wild swings from the expected (roboticized pre-flight airline announcements) to the inane (pet-store gerbils and a carton of raspberries costing the same amount of money), making the whole show feel almost claustrophobic. 

“Hell was a reaction to a lot of glitzy stand-up specials that I was seeing,” he says. “There’s a feeling you can see in a comic’s eyes, that they know that the material is going to work, so they’re kind of dead behind the eyes. I wanted to do an attempt at that, and encapsulate the reality of how I see [that kind of] performing, which is often grim.

“Doing that was very cleansing for me,” he continues. And once he skewered that brand of comedy, he thought, “‘Let me do the flex.’ The big glamorous theater, red seats, a spotlight. I wanted to make something that’s fun to watch even when it’s on mute.” 

If watching Fleming prance around onstage in a velvet purple jumpsuit with removable sleeves and ruby red slippers isn’t eye-catching enough, the new 70-minute show is filled to the brim with rapid-fire takes on middle school tuba players, the majesty of Great Danes, and hat store twinks on power trips. Fleming’s sets feel like an interpretative dance-heavy trip through one person’s notes app list of intrusive thoughts. (They move around so much through all of this material that they joke the spotlight operator “was on the team that got Osama.”) 

Fleming’s energy is no different over Zoom, moving between a meandering thought process and intense consideration of a question. In the midst of the interview, and sips of boba, Fleming takes off a fuzzy looking quarter-zip, only to reveal another, even brighter, quarter-zip underneath it. He later gets concerned about the boba. “Is it OK that I’m chewing the boba? Is that disrespectful? Because to me, this is a sign of trust for me to chew boba in front of you.” 

That’s the endearing nature of Fleming’s work in a nutshell. He can go long on how people are definitely going to have shitty kids, but he still cares how his interpersonal interactions are perceived. His comedy, and his general outlook, strikes a balance between knowing how to get applause and learning how to live without it — an attitude his early introduction to the world of social media likely enhanced. And with the release of Live at the Palace, there’s a clear part of Fleming that hopes to show other comedians a way to live with the reactions of online hordes, without letting the fear of them change their work. 

“We’re focusing too much on numbers, virality, whatever,” he says. “People can go viral and then they can’t sell out a 100-seat venue. You could have one million followers and not be able to get 20 people to show up to a show. So if you can land in people’s hearts, that’s way more important. Fuck awards. Fuck numbers. Fuck viral. If there’s something that I’ve done that you think about or feel later down the road, that’s the key. That’s what art should be.”