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.”
