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Worst Musical Moments in 50 Years of ‘SNL’

Saturday Night Live fans got an enormous appetizer for the show’s upcoming 50th-anniversary special this week in the form of Ladies & Gentlemen… 50 Years of SNL Music, an NBC-produced documentary that aired on the network and is streaming on Peacock. The special is worth watching for its opening section alone, which features a time-tripping, screen-splitting, beat-matching mash-up of SNL musical clips from the past 50 years; co-director Questlove probably could have just released that to YouTube to great acclaim. But the doc does go on (albeit without quite so much free-associative organizational inventiveness as its opening) to interview various musicians, cast members, and behind-the-scenes crew about the show’s music, both in terms of musical guests and the fine art of music-related comedy. (The Lonely Island, Adam Sandler, and Eddie Murphy, among others, are on hand to discuss some of their most famous musical bits.)

The 128-minute doc also gets into more controversial performances, like Sinéad O’Connor ripping up a picture of Pope John Paul II in 1992, the punk band Fear bringing along a bunch of slam-dancers in 1982 (at the behest of fan John Belushi, no less!), or Ashlee Simpson’s lip-syncing debacle in 2004. But the latter is an outlier in that it focuses on a performance that went spectacularly wrong. While O’Connor and Fear sometimes turn up on lists of the “worst” or most notorious SNL music moments, the less often-seen clips – music stuff from before the past decade or so often is scrubbed from the streaming versions on Peacock, presumably due to clearance difficulties/expenses – acquit the artists in question handily. Fear ripped it up, and seeing genuine moshing in Studio 8H is a thrill; O’Connor sang beautifully, and (as some SNL staffers sheepishly admit well after the fact) was essentially correct about the abuses of the Catholic church.

Simpson, though, is another story, especially when the doc gets ahold of some control-room audio, letting the audience in on the utter bafflement the show’s director and other staffers felt when the wrong backing track exposed Simpson’s earlier lip-syncing – and when her band pivoted into the right song, Simpson didn’t exactly take control of the situation and right the ship. (In footage that received plenty of pop-culture news play in the weeks afterward, she dances a little jig and then walks off, leaving her band in the lurch.) Simpson belongs in another category, largely and understandably avoided by Ladies and Gentlemen which is, after all, celebrating SNL’s power and influence. But there’s power and influence in some of its worst musical performances, too, which we will recount here, in chronological order.

  1. Red Hot Chili Peppers, 1992

    There were sloppy and/or ill-received musical performances on SNL before 1992, to be sure. But most of them just involve an alienating musician (Captain Beefheart, as covered in Ladies and Gentlemen, performed to crickets and one shout of “shit!” from the audience) or the band’s general vibe (yeah, the Replacements performed on the edge of collapse, but that was kind of their whole thing). Red Hot Chili Peppers, however, managed to make one of the most ubiquitous and beloved rock songs of their era sound genuinely terrible. The blame lies squarely on the demons of guitarist John Frusciante, who is visibly out of it throughout the performance, and whose barely-there guitar-playing drags the entire song down with him. Frusciante was suffering from the horrors of addiction at the time, and has been in and out of the Chili Peppers since. He seems to be doing vastly better these days, so the story has a happy ending, but in the moment it was a stunning screw-up.  

  2. Ashlee Simpson, 2004

    Look, the media is rough on young, female pop performers, ready to tear them down as inauthentic or inexperienced or insufficiently talented at any moment. Hell, this list of the worst SNL performances is majority female artists, and that kinda sucks. But it’s also hard to gin up much sympathy for Ashlee Simpson, the younger sister of singer/reality star Jessica Simpson, and her ultraproduced brand of pop-punk bubblegum, given that (regardless of the ethics of lip-syncing or how many other artists may have indulged in it over the years) her SNL mess-up showed that her first instinct was to shrug and walk away, and her second was to blame her band during the goodnights. This didn’t exactly end her career, but it certainly felt like a red flag.

  3. “Daiquiri Girl,” 2008

    Because Ladies and Gentlemen pays plenty of attention to the creation of musical sketches and videos, it’s only fair that one gets shouted out here. The Lonely Island became known for their hilarious genre parodies, often combined (especially in their early days) with an intentionally low-rent DIY sensibility. “Daiquiri Girl,” though, is just the DIY, no real genre parody, and little of the brilliant absurdity seen in their non-musical Digital Shorts. Andy Samberg sways and sings off-key about his “Daiquiri Girl” for about 35 seconds before a message scrolls on screen, informing the audience that the group had “a whole other video lined up with a famous musical act who bailed at the last minute.” It’s true: Gnarls Barkley bailed late Friday night, giving the trio virtually no time to throw something together for Saturday’s show. Lorne Michaels wanted a new Digital Short every week regardless, and “Daiquiri Girl” is the half-spiteful, half-abashed result. It’s a funny bit of trivia, but also deserves a spot of shame, less for the Lonely Island guys than for Lorne refusing to simply cede that 90 seconds to another segment, which would presumably not be difficult to do considering there’s always a dress-rehearsal version that runs at least a half-hour longer. In a weird way, it’s one of the more legit music-industry moments in the Lonely Island videography, with Lorne as a the grasping record producer insisting on soulless padding.

  4. Lana Del Rey, 2012

    Lana Del Rey played SNL when she was about to release Born to Die – not technically her first album, but her first project under her newly rechristened persona that would go on to become a figure of deep attachment, even worship, for her legions of fans, in the years ahead. With that longevity not yet confirmed, however, Del Rey wound up looking like a bad bet: Her SNL performances wobbled with obvious nerves, less spellbinding than a possible victim of hypnotism. She simply didn’t command the stage, and though “Video Games” was a hyped song in critical circles, it wasn’t yet well-known enough to serve as a proper distraction (or to make her awkwardness endearingly odd, rather than the primary focus). Obviously, Del Rey’s career recovered; for a while, every record she released was more breathlessly acclaimed than the last.

  5. Karmin, 2012

    Nothing went wrong with Karmin’s performance except the booking of it in the first place. The pop duo originated as relatively early YouTube faves, posting cutesy cover versions of popular songs augmented by mugging faces from frontwoman Amy Renee Noonan; then they prepped an EP of originals, and somehow scored a coveted SNL slot to promote it, debuting two songs on the show. They were beneficiaries of the unusual fact that 2012 was actually a big year for SNL taking chances on less established musicians. (It’s something they brag about doing in the Ladies and Gentlemen doc, but in reality only happens once in a while.) January and February 2012 saw a particularly obscure-for-the-show run: Lana Del Rey before her album came out, as mentioned above; Karmin before their first EP came out; and indie rock duo Sleigh Bells, beloved by certain fans but far from household names as their second album was released. In terms of pure audio quality – does this sound like the band probably wanted it to sound? – Karmin might have been the best of the bunch.

    In terms of the experience, though, it was pretty horrifying to see YouTube mugging from a white girl blatantly knocking off Nicki Minaj on a network-TV platform. (Maybe a content warning would have helped ease the audience into it?) It didn’t exactly cause a mass revolt but it did garner withering dismissals from the likes of SPIN, not least because this all went down a few hours after the death of Whitney Houston, whose pop music was not exactly cutting edge, but (as SPIN opined) didn’t have the mercenary edge of white YouTubers trying to recreate “Super Bass.” So yeah, the national music-fan mood was not great, Karmin failed to improve it, which more or less stopped their career dead in its tracks. Truthfully, this probably would have happened anyway at some point, but the SNL appearance seemed like a clear line in the sand. (Performances from this era of the show are generally not hard to find bootlegged on fan channels if they’re not in the NBC-sanctioned reruns, yet the Karmin clips seem to be pointedly scrubbed from the internet.) Undeterred, Noonan has since gone solo, and her songs are full-on rap numbers, seemingly based on the fact that she can talk nearly as fast as the MicroMachines guy from the ’80s. The real fallout may have been in the following SNL season (and beyond), where there were conspicuously fewer music bookings that could be qualified as risky.

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