If you are a fan of the thirty-nine-year-old comedian Chris Fleming, you might have trouble setting foot in a Trader Joe’s grocery store without thinking of a standup bit of his, known as “the Snacks at Trader Joe’s that Only Women Can See.” In the segment, which was filmed at the cozy Los Angeles venue Dynasty Typewriter, where Fleming is a regular presence, he puts forward a theory that women experience Trader Joe’s, with its ever-evolving inventory of newfangled snacks, as a kind of witchy laboratory of gastronomic discovery. Unlike most men—who make a beeline straight for the “same blue-corn tortilla chips that have been there since pre-Obama”—women swan dreamily through the store, “guided by their foremothers” toward the strangest possible products. “A woman’s relationship with Trader Joe’s is abstract,” Fleming says. “It’s like the way women see Trader Joe’s, it’s the way the aliens from ‘Arrival’ view time.”

The riff, which has more than a million views on YouTube, has become, over the past year, an in-joke among my female friends, who feel both seen by it and also even honored—a rare feeling when it comes to comedy that makes sweeping generalizations about feminine habits. From the outset of the bit, Fleming notes that he feels a certain kinship with women, by dint of his theatrical background, which includes training in acting and modern dance, and because of his androgynous physical appearance. Onstage, Fleming dresses in glam-rock getups reminiscent of both Mick Jagger and Cher. He has the shoulder-length curly hair of a pre-Raphaelite or an eighties mom with a perm. “I’m allowed on the perimeter of the coven,” he says. The punch line of the Trader Joe’s routine, in the end, is not that “women be shopping” but that women, at least in Fleming’s estimation, are enviably able to convert even the most mundane tasks into opportunities for creative transcendence.

In a way, this could also serve as a mission statement for Fleming’s own comedic philosophy. He revels in unearthing the weirdness of the everyday, and in pointing out that most people he encounters are simply not weird enough. There is an art-school mentality to the way Fleming splits up the world: there are the “freaks,” a group to which Fleming enthusiastically subscribes, and the “normies,” a catchall category of run-of-the-mill types who provide fodder for him to highlight his own hard-won quirks. He is a keen observer of the way in which eccentricity, once the provenance of true outcasts, has been gradually co-opted by corporations and by financially comfortable regular Joes who risk nothing in expressing it. Shortly into his new HBO special, “Chris Fleming: Live at the Palace,” which débuted in February, Fleming launches into a spiel about a hypothetical, utterly average man who is touted by his girlfriend as being “fun” because “he does interpretive dance at a wedding for a laugh.” “Listen, normies,” Fleming says, his voice growing gruff. “There is nothing fucking funny about interpretive dance. My costume is not your culture. Interpretive dance is how I keep my lights on, and pay my astronomically high emergency-vet bills! ” Wearing a bright-purple jumpsuit with a bejewelled waist and glittery, red Dorothy-in-Oz loafers, Fleming caps the assertion by performing a balletic lunge across the stage.

Fleming’s HBO special, his first for the network, is his chance to tip into mainstream comedy after more than a decade as a cult figure. (Or, as he puts it at the start of the show, “I’m trying to grow my audience beyond women who brought a knife to prom.”) It is also, by far, his most accessible work, ouching on various ostensibly conventional millennial-friendly subjects, including Lin-Manuel Miranda, kombucha, Fleet Foxes, and the interviewing technique of Terry Gross.

What keeps Fleming’s observational humor from being banal—and shifts it into almost a meta-statement on banal observational comedy—is the oddball physicality that he brings to his act and his ability to extend a bit, through exaggerated pantomime, past the point of logic and into a more heightened and absurdist realm. In his bit about the toppings at ice-cream shops, he first notes the way that Oreos tend to be pulverized beyond recognition, then muses that whoever is responsible for the brand at Nabisco must be a sadist. He then launches into an invented phone conversation between “the frozen-dessert world” and “Mr. Nabisco,” a sinister character who sounds not unlike Hannibal Lecter, who, when asked about how he prefers Oreos to be treated by ice-cream purveyors, answers, with a creepy flatness, “Do whatever you want to them. Disgrace them. Degrade and humiliate them. Chop them up.” His Terry Gross reverie climaxes with him yelling, at an imaginary Adam Driver, “You don’t get to call me Terry Gross. Terry Gross is my nickname. My real name is Theresa Disgusting!”

At the same time, the new special marks a reining in of some of Fleming’s more experimental instincts. He first gained notice online in the mid-twenty-tens for a series of D.I.Y. short films that had the feel of messy, spontaneous performance art. His characters included Gayle Waters-Waters, a histrionic suburban woman based, in part, on his own mother, who co-starred as Gayle’s friend Bonnie. In “DiPiglio,” perhaps the most beloved of those early segments, he struts down a sunny street while being chased by a tiny, toothy monster created by primitive computer animation; when a bystander mentions concern for his safety, Fleming asks, ungrammatically, “Should I run about this?” He made a barely comprehensible sitcom pilot, called “i’m the Mayor of Bimmi Gardens,” which he posted directly to YouTube; it follows Fleming as he swans around a “Pee-wee’s Playhouse”-esque set of a fictional Florida hamlet, playing a mayor who is trying to save the town’s “Boba crops.” A 2023 special, “Hell,” which aired on Peacock, was only slightly more approachable, involving surrealist skits and filmed segments featuring papier-mâché-like crafts.

When Fleming’s lo-fi approach worked, it felt like a delicious secret. During the pandemic, he released a series of short free-form disquisitions delivered from his car, and a series of original “songs” in which he’d monologue and warble over computer-generated synths, like an internet-addled Laurie Anderson. I first discovered Fleming’s work when I stumbled across one such number, called “Sick Jan,” in which he relayed the story of his accountant, a frumpy woman named Jan who played fast and loose with tax law. (“Sick Jan, we don’t have to claim a home office/If it means we’ll both go to jail,” he sings.) The song was so intricately detailed, its protagonist so particular—she has a “gray buzz cut and enough turquoise to get into Stevie Nicks’s house”—that it sparked within me a sense of sudden understanding. I didn’t know Sick Jan, but I’d known many Jan-like women, who before that very moment I’d never quite had the language to describe.

A similar linguistic specificity and precision-guided kookiness animates Fleming’s standup work. He is a master of the unexpected, idiosyncratic analogy. In one popular bit, in which he talks about baby boomers’ attachment to using Bitmojis, he says that “not since Goodall went into the jungle have we made such strides towards comprehending such a mystifying population.” He starts out another much-shared routine with “You know that thing where the most toxic person you’ve ever met over-relates to woodland creatures on social media? I call it ‘vibe dysphoria.’ ” He continues, “I don’t know how you got under the impression that you are a mouse in a jean jacket. You are an eel with a gun.” In “Live at the Palace,” one of Fleming’s biggest laughs comes when he describes his fellow-comedian Mike Birbiglia as looking like “a father and son ‘Freaky Friday’-ed into the same body.”

Even Fleming’s more conventional observational humor is inextricable from his outre bodily maneuvers onstage. Early in the special, he trots like a show pony, explaining that he got a jaywalking ticket in Los Angeles for his tendency to engage in “fanciful street dressage.” He impersonates a Clumber spaniel by freezing in a plank pose, crashes to the floor to depict a kid falling under the weight of a tuba, scuttles around like a crab, takes a running, belly-first leap onto a stool, and undulates on the ground to suggest the germs crawling around on an unwashed cast-iron skillet. At one point, he thanks the spotlight operator, who he says “was on the team that got Osama,” then scurries frantically around the stage, tripping over his own legs, in an attempt to outrun the spot. Fleming’s long hair and prancerly mien have led to much puzzlement over his gender identity, or what he calls in the HBO special “a nationwide manhunt for my pronouns.” In the show, he makes no pronouncement, but just tells the crowd, “You tell me. You’re looking at it.” Fleming’s defiance of categorization is what makes him feel like a generational talent: he is both a wordsmith and a clown, a person obsessed with “normie” habits who shows us just how alien the normal can be. ♦