Season 2, Episode 14
As one of the most stylish rock stars of all time, Elton John's guest appearance in Season 2 was of course going to make this list. His wild outfits were just as well-known as his music, and he has Chef to thank for that. When Elton John was first getting his start and struggling, Chef put him in touch with a songwriter and told him to "get yourself some new threads. You know, some slick glasses and shit!" Cut to today, and Elton's wearing an insane all-white outfit with purple stars and some slick glasses.