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“Saturday Night Live”: The 21 Most Embarrassing Musical Guests Ever

Saturday Night Live launched its 40th season last weekend,, and it was a shaky start–even wth Chris Pratt hosting and Ariana Grande handling musical guest duties. Our hopes were guardedly optimistic. Mainly, we were just hoping Ariana was going to offer up something different than white go-go boots.

But for all the (too often deserved) criticism of the show’s comedy content of late, few have pointed out how wide-ranging and innovatively presented SNL’s music segments have become over the past few years. Last season alone featured excellent, creatively mounted sets by Drake, Haim, Sam Smith, the Black Keys–and, in a particularly outstanding (and rare) match-up of inventive artist and network nerve, St. Vincent.

Alas, it’s perennially popular, instead, to lament famous SNL musical misfires committed by the likes of Lana Del Rey (droning like a mannequin made of Quaaludes), and Sinead O’Connor (ripping up a picture of the pope). Those ladies may (or may not) lament those moments, but each was at least failure of ambition—and each star has been incalculably more famous ever since.

The following round-up of dead-on-arrival Saturday Night Live music shots all count as legitimately mortifying. Pretention, incompetence, hubris, and just plain suckiness define these artists’ efforts before a live audience of millions.

Now open your ears and hold your nose for Saturday Night Live’s 20 most embarrassing musical guests ever–which shouldn’t be mistaken with Saturday Night Live‘s Most Forgotten Musical Acts, although both have a few in common…