1. Phil Collins ('Phil the Shill,' Season Two)
A year after his "In The Air Tonight" soundtracked the single most defining musical moment of Miami Vice's first season (and arguably the entire series), Phil Collins appeared on the show as Phil Mayhem, the con-artist host of a TV game show called Rat Race. "Phil the Shill" (which also featured a young Kyra Sedgwick) ranks among Vice's funniest episodes thanks to the comic chemistry between Collins and cast goofballs Martin Ferrero ("Izzy Moreno") and Michael Talbott ("Stan Switek"). Collins even recorded a parodic theme song for Rat Race, which brilliantly bookends the episode.