5. Red Hot Chili Peppers/Bette Midler/Barry White - (S4 E22 - "Krusty Gets Kancelled)
When Krusty is replaced by the unimpressive Gabbo, the Red Hot Chili Peppers strip down to their gym socks for Krusty's comeback special which also included Bette Midler and Barry White, two people you may have to ask your parents about. Only four years into their run, at a time when many critics were still trying to figure out exactly who the Simpsons was aimed at the show's producers messed with them further by creating their first multi-musical act show with a cross-generational theme. On one hand there was the Red Hot Chili Peppers which appealed to the younger generation. Then there was Bette Midler who appealed to that generation's parents and to top it off with a healthy dose of the sexy baritone of Barry White and critics still had no idea who the Simpsons was aimed at. They would repeat this musical juggling act with much more effectiveness in thanks to Lollapalooza.