I think people like the Simpsons episodes they saw when they were kids the most. For this reason, a lot of my favorite Simpsons episodes get up to like, seasons 14 and 15.

The iPod Nano was a reference to "Art of Discourse," when, during the food fight montage, she is listed as "Proud Owner, Used iPod Nano, 2014." So there you have it. The origin story of a throwaway gag.