5. Rob Corddry (Alan, Season 2-Accounting For Lawyers)
Rob Corddry has made a career out of being a smug dick in most of his roles, and thats the case on Community as well, where he plays Alan, a former law firm partner of Jeffs. Hes at Greendale for Narcotics Anonymous, but hes still down for drinks with his old buddy Jeff (I stopped doing blow, not being awesome he explains). Annie recognizes him from NA, though, and explains that he told a story about getting Jeff disbarred. The group then follows Jeff and Alan to a party at his old law firm (run by Drew Carey, in another great guest role for the show) to find evidence of Alans actions. Annie gets the office number from Alan (At first, he told me it was 69) and her, Abed and Troy go up to the office, resulting in possibly the best .gif ever:
