4 Absolutely Terrible ‘SNL’ Musical Guests

Lend me an ear, and I’ll sing you a song and I’ll try not to sing out of key

Give it up to Questlove — his new documentary, Ladies & Gentlemen… 50 Years of SNL Music, is killer, especially its imaginative opening montage of musical mash-ups. But while Questlove (mostly) wanted to honor SNL’s long history of eclectic, electric performances, not every musical guest delivered the goods. I’m not talking about musicians who turned in great performances but still caused the show headaches, like Sinead O’Connor, Rage Against the Machine or Elvis Costello either. Instead, let’s check out four outright terrible performances that belong in the show’s musical Hall of Shame.

Ashlee Simpson

The undisputed champion, and a performance memorably bad enough to make Questlove’s documentary. Can we even call it a performance? 50 Years of SNL Music explains that Simpson’s voice was nearly shot the night Jude Law hosted, necessitating a compromise in which she’d sing one song live and lip-sync the other. By show time, she’d decided to Milli Vanilli both of them. Simpson is likely not the first or last performer to pretend to sing on SNL, but she’s the only one who had the wrong vocal track cued up on live television, leading to a self-immolating jig when she was found out. Humiliated, she shuffled off into the wings, leaving her band to suffer alone on stage until SNL mercifully cut to commercial. 

Captain Beefheart

Bad is in the ear of the beholder, apparently, because according to 50 Years of SNL Music, Jack White and his pals relished their VHS tape of Captain Beefheart’s performance. “That was one of my favorites,” the White Stripes frontman has explained.

SNL sketch music producer Hal Willner, however, acknowledges that most thought the set was a disaster. “Captain Beefheart, if you have ever heard his music, he has tones that a lot of people can’t handle,” he confessed. “Not one person in the audience clapped.” The crowd’s deafening silence did nothing to cover up the one audience member who yelled “Shit!” as a one-word critique.  

Lana Del Rey

Was Del Rey merely nervous when she sleepwalked through a rendition of her hit “Video Games”? Whatever was to blame, the stiff performance was memorable enough that Del Rey was approached to appear in Ladies and Gentlemen… to break down the debacle. She (and Simpson) declined.

It probably didn’t help that Kristen Wiig turned Del Rey into a Weekend Update character just a few weeks later. Wiig’s devastating parody said the dead-eyed, somnambulate part out loud. “Based on the public’s response,” whispered Wiig/Del Rey, “I must have clubbed a baby seal while singing the Taliban national anthem.”

Kanye West

If Lorne Michael’s problem with Sinead O’Connor was that her picture-ripping stunt took him by surprise, what must he have made of Ye’s MAGA hat and unhinged rant at the end of his “Ghost Town” performance in Season 44?

Ego Nwodim was a brand new cast member when she found herself onstage during the off-script detour. “I was like, ‘I don’t wanna be up here for this, and I don’t agree with this, and standing up here looks like I’m standing in solidarity,’” she explained. 

Kenan Thompson knew better than to hang around, making a hasty exit when he saw what was coming. “When he grabbed the mic, and was just wandering around, you could see that he was gearing up to say something. I was like, ‘I’m out!’ It would have been cool if he just had did the music thing, and, I don’t know, just spoke through the hat, I guess, ‘cause the hat was loud.”

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