Every "Outstanding Comedy Series" Emmy winner ever, ranked in order of preference by the Ranker community. Vote for your favorite all-time comedy series on the list below and vote down the ones you don't like. The Outstanding Comedy Series Emmy award was first handed out in 1953, only 4 years after the creation of the Emmy Awards.The show that has won the award the most times is "Frasier," with 5 wins. Both "Cheers" and "M*A*S*H" were nominated for the award a record 11 times. More recently, "30 Rock" swept the award for 3 straight years from 2007 to 2009. There have also been many notable, popular comedy shows that have been snubbed by the Emmys, including "Curb Your Enthusiasm," "Two and a Half Men" and "Roseanne."