Oscar Madison, played by Matthew Perry, is a sports talk show host. Like his friend Felix, Oscar is a divorcee, but his wife Gaby left him because she thought he was a thoughtless slob. Oscar now lives with Felix, but the two often clash because Felix is a neat freak and Oscar is very slovenly and more easy going.

He is the sixth incarnation of Oscar Madison following Walter Matthau in the 1965 play, the 1968 film adaptation, and its 1998 sequel, Jack Klugman in the 1970s television series and its made-for-tv film The Odd Couple: Together Again, a cartoon adaptation named Fleabag the Dog in the Oddball Couple, Demond Wilson in The New Odd Couple, and Rita Moreno as Olive in The Female Odd Couple.