3. Tony Bennett - (S2 E5 "Dancin' Homer")
The episode features a guest appearance by singer Tony Bennett, who was the first guest star to appear as himself on The Simpsons starting the trend that was to become commonplace for the next two decades . Bennett appears in a scene in which the Simpson family meet him while taking a tour of Capital City after Homer gets a chance to take his team mascot 'Dancin' Homer' character to the big leagues backing up the Capital City goofball. While his appearance didn't skewer to the younger set who had no idea who Tony Bennett was (a theme that continued in the years to come) it struck a chord with the producers who decided to start actively requesting personal favourites to guest-star, if nothing more than their own chance to meet their musical idols. Tony Bennett also sang the song called "Capital City" much like "New York, New York" over the closing credits.