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In doing research for a piece about the best late night comedy sets of the 2010s, memories of one of the most bizarre TV moments of the decade came rushing back: remember that time Madonna did standup on The Tonight Show Starring Jimmy Fallon? Back in 2015, she was hitting the talk show circuit in promotion of her new album, Rebel Heart, a genre-hopping collection of tracks that featured collaborations with a wild group of folks, including Kanye West, Alicia Keys, and Mike Tyson. In keeping with the tonal chaos of the record, Madonna, ever the polymath, decided to try her hand at stand up comedy one night on Fallon.

Watching the clip now, the spontaneity of it all is obviously canned, but that’s where the certainty ends. Did she actually write these jokes? Is she really this nervous? Is this all a high-concept bit? It’s a struggle to wrap your mind around the conversations that went into this, whose idea it was in the first place, and how much of a self-conscious stunt it is. Is this a sincere attempt by a person so isolated from real feedback that they struggle to connect with an audience in this extremely direct art form or just another over-engineered swing at going viral from a late night talk show?

Whatever level of irony this thing is vibrating on, it’s a brain-melter to witness. She’s in a constant struggle to wrangle the audiences perception at all times, getting distracted by the confused response to her jokes about being an extremely wealthy person who dates men in their twenties. “It’s funny,” she assures them, after a reference to her massive collection of Warhols. If you’ve ever stumbled upon a comedy open mic, you’re familiar with this energy: an otherwise confident person on stage in conflict with themselves, unsure as to why they’re not immediately good at this, too.

All that aside, it’s honestly nice to see something so strange on a show as high-profile and choreographed as Fallon. Let’s all agree: less Carpool Karaoke, more unpolished standup meltdowns on late night in 2020!

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