The Simpsons: 10 Worst Guest Stars Ever

1. N'SYNC

Episode: Season 12, "New Kids on the Blecch" Bart and his friends form a boy band. That's an easy pitch for an episode, right? Unfortunately, it just wasn't very good. Boy bands have never been "cool" and should never be what The Simpsons' aspires to be. We all know the life of a boy band by now: they have a big hit or two, are loved by tweens, then fall apart, and one or two members, maybe, make it in solo careers. For reference, see New Kids on the Block, N'Sync, Backstreet Boys, and heck it'll probably happen to One Direction soon if it hasn't already. Boy bands are always very dated products of their time, so going back and watching this episode, you almost feel embarrassed by how bad N'SYNC's guest spot was, even though Justin Timberlake has turned out to be a pretty decent talent, able to poke fun at himself and excel at comedic roles like his spot in Bad Teacher. The entire episode was a mess, and even the homage to Mad Magazine couldn't save it. Plus it had the bizarre plotline where the Navy is behind Bart's whole boy band in order to subliminally recruit new members. Overall, terrible, and N'SYNC's atrociously trendy guest spot was its low point. Any we missed? Add them below!
Contributor
Contributor

Primarily covering the sport of MMA from Ontario, Canada, Jay Anderson has been writing for various publications covering sports, technology, and pop culture since 2001. Jay holds an Honours Bachelor of Arts degree in English from the University of Guelph, and a Certificate in Leadership Skills from Humber College.