Walter Matthau

Matthau's screen career got moving in the late 1950s, with supporting turns in A Face in the Crowd (1957) and King Creole (1958) — the latter an Elvis Presley vehicle, which isn't where you'd necessarily expect to find a future Oscar winner, but Matthau was always good at showing up in unexpected places. He wasn't the lead yet. Character work, scene-stealing, building a reputation. The real turning point was The Fortune Cookie (1966), Billy Wilder's sharp comedy in which Matthau played a scheming lawyer named Whiplash Willie — a performance so committed and so funny that it earned him the Academy Award for Best Supporting Actor. Broadway had already recognized him by then: he'd won the Tony Award for Best Actor in a Play in 1965 for originating the role of Oscar Madison in Neil Simon's The Odd Couple, his second Tony after A Shot in the Dark in 1962. He also received a Primetime Emmy Award nomination in 1963 for his performance in The DuPont Show of the Week (Wikipedia). The stage work clearly sharpened him. Through the 1970s, Matthau hit a remarkable run — Plaza Suite (1971), Charley Varrick (1973), The Sunshine Boys (1975), The Bad News Bears (1976), California Suite (1978), Hopscotch (1980). That's a stretch of films that holds up. His Bad News Bears coach, Morris Buttermaker, is one of those roles where you can practically smell the beer-in-the-dugout atmosphere he brings to every scene. He kept working well into the 1990s, reuniting with Lemmon for Grumpy Old Men (1993) and cementing a late-career warmth that sat comfortably alongside his earlier, sharper edges.