Madonna Does Stand-Up Comedy

In her 30-plus years as a pop legend, cultural icon and occasional iconoclast, Madonna has never shied away from challenges. As anyone who’s seen Shanghai Surprise can tell you, sometimes she should.

On Thursday’s Tonight Show, Jimmy Fallon gave the Material Girl room to fulfill a dream of hers: to do stand-up comedy. Her three-minute routine was either the biggest bomb in late-night history or the most subversive, introspective critique of superstardom ever broadcast to a mass audience.

“I just think it’s always good to talk about what you know,” Madge told the audience at the opening of her set. “I’m gonna start with dating younger men.” She proceeded to fumble charmingly through anecdotes about asking her teenage son if any of his friends are single, and about her past conquests who didn’t know Warhol, Picasso or any other artists whose original and insanely expensive works hang in her home.

To be fair, Madonna looked fantastic and was clearly having fun. She also recovered later with her musical performances, including a rendition of “Holiday” with Fallon and the Roots. But even if her comedy routine was funnier than Who’s That Girl?—though maybe not Body of Evidence—she shouldn’t quit her day job.