Jack Klugman vs Tony Randall
Show: The Odd Couple
Rivalry years: 1971-1975
Who won: Klugman, 2; Randall, 1
The legendary stars went up against each other for the Best Actor in a Comedy Series all five years the show was on the air (1970-1975). Klugman won twice for his role of Oscar Madison — in 1971 and 1973 — while Randall (as Felix Unger) walked away with the award once, for the series' final season in 1975. They both lost twice: in 1972 to All in the Family's Carroll O'Connor and in 1974 to M*A*S*H's Alan Alda.