The Simpsons: 10 Guest Spots That Almost Went To Someone Else
9. N*Sync in “New Kids On The Blecch”
In Season 12, The Simpsons decided to take a shot at boybands by having Bart, Milhouse, Nelson, and Ralph form their own. The Party Posse enthralled fans with their catchy hooks and dank beatz, but were actually just a front for a subliminal navy recruitment scheme.
To spice this episode up, the show wanted an actual boyband to appear in Springfield. Their first choice was The Backstreet Boys, but that plan was dashed almost immediately. The band declined the guest appearance, claiming that it would "embarrass" them and their fans. Ah yes, The Backstreet Boys, famous for their seriousness.
The writers presumably asked their kids who else they liked and the name they came up with was N*SYNC. The group (including a young Justin Timberlake) were delighted to appear on the show and delivered an excellent performance that included the now-famous "Word!" line from JT.
It's hard to say how this episode would have differed had it featured BSB, but it's hard to see them topping N*SYNC's appearance. But hey, N*SYNC broke up the year after this episode came out and The Backstreet Boys are still together, so maybe they were right after all.