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This Chris Fleming Bit Explains Why Conan O'Brien Loves Them So Much
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This Chris Fleming Bit Explains Why Conan O’Brien Loves Them So Much

By Andrew Sanford | News | September 4, 2025

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Header Image Source: Photo by Arturo Holmes/Getty Images for Tribeca Festival

Conan O’Brien, looking directly into the camera, milk-stained, eyes bulging, skin as red as a Florida resident, pleading with people to open their minds to older forms of comedy, is one of my favorite things he’s ever done. It’s couched in one of the greatest moments of his career. His appearance on Hot Ones is both chaotically hilarious and touchingly wise. I have his answer cued up below.

It’s not just that what he’s saying is good advice; it’s that you know he not only follows it, but also believes in exploring newer comedy as well. It makes sense. Conan was the new, weird, late-night guy at one point, and let’s be honest, weird still applies. However, the man took his sizable platform and ever-growing popularity to prop up new voices as well, either as stand-ups (like Marc Maron) or actors (like Amy Poehler).

Conan’s support of new comedians continues. He recently appeared in Please Don’t Destroy: The Treasure of Foggy Mountain, a movie by the former SNL troupe. O’Brien also had comedian Chris Fleming on his podcast, and his love for the YouTube star is apparent, infectious, and makes a hell of a lot of sense. Not only is Fleming a fellow Massachusetts native who shares some visual similarities with O’Brien’s ilk, but their comedy is absurd.

While Fleming first hit it big with their series Gayle on YouTube, which saw them playing a ridiculously intense suburban mom. It was a character they developed in their stand-up, which can include everything from wild physical comedy to clips from Grease to a six-piece band. It knows no bounds in a way that feels very similar, and, obviously, attractive to Conan O’Brien.

O’Brien gushed over Fleming on the latest episode of Conan O’Brien Needs a Friend, showering him with praise, and noting how he will outright assault him (playfully) at parties and at his home, as he considers Chris to be like a brother. The long-time late-night host praised Fleming not only as a comedian but as a person, and look, I don’t know Conan personally, but I am going to say with certainty (mock certainty, but still) that the following clip made Conan into a permanent Fleming fan.

I howl every time I watch that bit. The idea alone, that Elton John’s famous recording of Bennie and the Jets sounds like he’s forced to perform by the end, but the commitment and physical comedy are next level. It feels very “Conan-Coded,” as the children may say. Perhaps I’m projecting, as this is the bit that turned me into a fan of Fleming, but I can at least somewhat confidently assume Conan watched and liked it.

Listen to the way he talks about the guy! He acknowledges having his guard down around him. He speaks so highly of him. It’s truly lovely.