The absurdist sad clown is an evergreen character because he sits so explicitly where comedy and tragedy intersect, which is deeply familiar to us all. What am I doing here, he laments wordlessly, smiling through tears, why is everything so beautiful and so ugly all at once? Puddles is a contemporary version of this trope, singing covers of pop songs in his rich baritone. It all hangs together by a thread—it wouldn’t work if his voice weren’t so good, or if he weren’t, at 6’8”, the ridiculously physically imposing, fully committed ringleader of what he calls “Puddles Pity Party.”

Postmodern Jukebox feat. Puddles Pity Party, “Royals,” written by Joel Little and Lourde, 2013.

This post is part of Music 100, a love letter to songs. 100 words on 100 songs in 100 days, running from Groundhog Day to 4th of July, 2025.

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