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.
