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Comedian Chris Fleming is set to electrify audiences in Chicago as he records his debut stand-up special for HBO. Known for his energetic performances and sharp insights into life, pop culture, and our collective tendency to act as though everything is perfectly normal, Fleming is prepared to make a significant mark. With none other than Massachusetts comedy legend Conan O’Brien on board as an executive producer, Fleming’s journey, which spans over two decades, is reaching a new pinnacle in the comedy world.
The Essentials: If Chris Fleming’s name rings a bell but you’re not fully acquainted with his work, chances are you’ve encountered his viral social media clips. These showcase his fiery comedic opinions, both on stage and as a guest on various podcasts. His repertoire includes two prior specials: Showpig, available on YouTube and Facebook, and the 2023 release Hell on Peacock.
Fleming has also made appearances in popular TV series such as Abbott Elementary and Loot, along with numerous guest spots on CBS’s late-night show, After Midnight.
In this HBO special, Fleming, a Skidmore graduate who hails from Boston’s western suburbs, turns his comedic lens on himself and his upbringing, offering audiences a humorous self-reflection.
Which Comedy Special Does It Evoke? Imagine merging the comedic genius of Maria Bamford with the artistic flair of Prince, and you’ll have a sense of what Fleming’s special promises to deliver.
Memorable Jokes: What do Seth Meyers, Terry Gross, Adam Driver, Lin-Manuel Miranda, Oreo’s, the president of Skidmore College, and Mike Birbiglia have in common? They’re all fodder for premises and/or references in Fleming’s routines, which exhibit both choreographic and linguistic flair.
One moment he’s weighing the relative personality traits of different dog breeds. Another he’s imagining the demented business practices that’s allowing one of America’s favorite treats to top a dessert untouched, while the other is deconstructed and demolished almost beyond recognition, if still within the bounds of literally good taste.
He’s equally adept at acting out an imagined scenario in which NPR host Terry Gross chases the actor Adam Driver down the street after their interview got cut short, as he is inhabiting the inanimate cast-iron skillet that has come alive after too many years without a proper cleanse.
Fleming also pokes fun at himself, revealing how he fumbled a response when Lin-Manuel Miranda reacted favorably to one of his Instagram clips; how in a rare moment of feeling hyper-masculine, a stranger confused him for an elderly actress; and how his ego got the better of his bank account in a hat store with his guy friends. Do you doubt him? “You think I’m not gonna bring receipts,” he crows.
Our Take: Fleming doesn’t run around the stage so much as he prances, skips and bounces like a one-man ballet. He even jokes at one point that interpretative dance is keeping his finances afloat. Or is he keeping the interpretative dance community afloat?
Either way, he’s nurtured a look and a presence all his own. A custom purple one-piece with tearaway sleeves. Sparkly ruby red slippers evoke a sense that we the audience are in Oz with Fleming.
Does that make him Dorothy? Does it even matter? As he jokes: “I released a special two years ago and it sparked a nationwide manhunt for my pronouns.’ Fleming is not about to give you easy clear-cut answers, nor should he have to. He’s content enough to let us know how strangers can roast him without meaning to, and how even as a sixth-grader, his peers knew he was not like the other kids. The older kid at the lake feared harming Fleming, apparently: “He sees something in me that he deems unthrowable.” Never mind that young Chris wanted to be thrown, or that older Chris throws himself about the stage with complete abandon.
He might’ve appeared more fragile in his childhood. But now, grown into his own skin both emotionally and comedically, he shows us that what looks like fanciful whimsy is not just for show. Oh, it’s for show, alright, but also for show business. The mischievous glint in his eyes as he delivers lines like “cheddar is getting sharper every year,” or deliberately starting another bit over without edits just because he didn’t like the path an ad-lib led him down.
He knows where he’s going, even if his audience might not have a clue.
“I’m trying to grow my fan base beyond women who brought a knife to prom,” he jokes in his opening minute. By the end of his closing number, you’ll be wanting to crown him king and queen of the prom.
Our Call: STREAM IT! While other platforms (Hulu, Amazon Prime) throw bags of money to lure big-name comedians away from Netflix, HBO has remained the tried-and-true home for the best voices in comedy, whether they’re already famous household names or should be. It’s gratifying to see Chris Fleming stay true to the vision he had starting out in stand-up two decades ago and be richly rewarded for it. Strap in and enjoy the ride!
Sean L. McCarthy works the comedy beat. He also podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.
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