10 Worst Things Krusty The Clown Has Ever Done

1. He Got Married FOURTEEN Times

Episode: "Once Upon a Time in Springfield" (Season 21, Episode 10)

The one thing worse than cutting Saddam Hussein a break? Convincing a staggering 14 women to marry him, as mentioned shortly before his intended wedding to Princess Penelope.

A generous reading might call Krusty a hopeless romantic, but you'd think the guy might learn a thing or two about alimony after his first four or five marriages failed - him being a rich celeb and all.

Krusty's penchant for tying the knot was brought up by Bart and Milhouse at his wedding to Penelope, noting that his first wife was the free-loving Holly Hippie (who he wouldn't let watch the moon landing), and his most recent wife was legendary singer-actress Eartha Kitt, who Krusty married for a whole six hours (five of which he was asleep).

This resulted in a rare merciful deed from Krusty: refusing to marry Penelope because he'd soon enough ruin her life by making her his 15th divorce. Does that count as personal growth?

Still, there's a point, a long time before 14 divorces, where you really need to hang it up and let the reality wash over you: you're not marriage material.

If betting against the Harlem Globetrotters was his most egregious act of self-destruction, this was pretty damn close.