24 seasons and over 500 episodes in, the Simpsons has established itself in the domain of pop culture for good, regardless of where and when you believe the show began a downward trend in quality. One thing that has kept it alive this long is that in lieu of writing stories focused on the central Simpson family or even the supporting cast, the show has become a sort of guest-star mill, featuring whatever flavor-of-the-week celebrity will agree to appear on the show.
That means a lot of musicians have shown up on there as well. In fact, the Simpsons has long been renowned for featuring some of the greatest musicians of all time in some of the greatest scenes in the show's history. All three Beatles and Michael Jackson have shown up in the past to wide critical acclaim.
But in recent years, music has become sort of a blight on the show. In ratings-grab stunt-casting, the show has featured some awful musician cameos that have embarrassed all parties involved. These are the five worst the series has ever featured.
5. N*SYNC In a weak parody of boy bands that came just slightly too late in 2001, N*SYNC showed up to bolster the episode "New Kids on the Blecch" from Season 12. The episode's relevance is immediately cast into question by the dated title reference, but I'll let that slide.
The episode itself is no better or worse than many Season 12 episodes, but N*SYNC's appearance is more worthless stunt-casting. The only fit of inspiration here is reusing the recording of Justin Timberlake saying "word" over and over again because he initially refused to say it. Otherwise, just watch South Park's parody of boy bands instead.
4. The White Stripes Heavily promoted in 2006, the White Stripes finally made a Simpsons appearance in the Season 18 episode "Jazzy and the Pussycats" wherein Bart starts playing the drums to vent aggression. You'd think they would have gone with some really famous and highly regarded drummers for this episode, but, again, ratings and stunt-casting called.
So the White Stripes show up in a frame-for-frame recreation of their "Hardest Button to Button" video, apropros of absolutely nothing despite the entire episode being promoted based on the guest appearance. Then Bart gets bit by a tiger for some reason. It's best just to move on at this point.
3. The Baha Men The Baha Men were a questionable choice to guest star on The Simpsons to begin with, primarily because they were clearly one hit wonders who made a mildly amusing novelty song that no one could escape in the year 2000. But then, the entire premise of the episode was questionable, so why the hell not?
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The Baha Men show up in 2002's Season 14 episode "Large Marge," two years late on the bandwagon to begin with, and wherein Marge accidentally gets breast implants. Yeah. Anyway, things get even worse when the Baha Men show up to perform new versions of their annoying hit with the lyrics "who let her jugs out" and "who let the milk out." Kill me now.
2. Ke$ha Whether this one counts as a guest appearance is questionable, but it is one of the worst moments in Simpsons history and features the music of Ke$ha, so there you go. Even though this couch gag of the Simpsons characters performing Kesha's hit "Tik Tok" from the Season 21 episode "To Surveil With Love" only lasts a little more than a minute, everyone involved somehow loses my respect a little bit more for each second it goes on.
It's a really shameful attention-grabbing stunt, but it works for all the wrong reasons. Ke$ha hardly needed the bump herself in 2010, with the song literally being everywhere. So then the only explanation for it is that the Simpsons thought they could get a bump off of it, but in the end it's sort of like watching your grandpa try to rap.
1. Kid Rock As awful as all those others on this list are, I have to admit that there's a caveat to how bad they were: they took place long after my personal cutoff for when the show stopped being good. That's why Kid Rock's appearance in Season 11's "Kill the Alligator and Run" is No. 1 here.
Not only is the episode absolutely dreadful, and Kid Rock's cameo completely pointless, but it marks the turning point when I personally realized that The Simpsons was never going to be a great show again. It came on the heels of a wildly successful run for the first nine seasons and even if Season 10 had its ups and downs, it seemed like the show could still rebound.
This episode, however, ended up being unwatchable. So congrats, Kid Rock. Whether you meant to or not, you will forever be associated in my mind with the day that one of the greatest shows of all time started to suck.
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