Though he turned out to be a cute (grumpy) old man, Walter Matthau's appearance and curmudgeonly attitude made the actor seem more suited for a tucked-away desk job. Instead, he found much success on both stage and screen. In 1968's The Odd Couple, Matthau's portrayal of the droopy-faced and sloppy Oscar Madison was the definition of "lovable loser." Indeed, his performance was so lauded that he would go on to star in the role in both the Broadway and Hollywood productions. His acting cred was boosted with a Best Supporting Actor Oscar for his role as a shyster lawyer in The Fortune Cookie, and again when he played the fan favorite in Grumpy Old Men.