Jason Alexander vs Michael Richards
Rivalry years: 1992-1997
Who won: Richards, 3
Amazingly, neither Jerry Seinfeld (playing himself) nor Alexander (George Costanza) ever won an Emmy for their roles on the iconic sitcom, which ran from 1989-1998 and has reached greatest-sitcom-ever status over the years. But Richards pocketed three statuettes for Best Supporting Actor in a Comedy Series for bringing Kramer to life during that time — triumphing over Alexander in 1993, 1994 and 1997 (they were both defeated in 1995 by Frasier's David Hyde Pierce and 1996 by The Larry Sanders Show's Rip Torn). Speaking of Seinfeld wins: Julia Louis-Dreyfus also won for Best Supporting Actress in a Comedy Series in 1996 for her turn as Elaine Benes.