John Seymour Erwin · Public domain

Walter Matthau made ten films with his real-life friend Jack Lemmon, a pairing the New York Times called one of Hollywood's most successful, beginning with The Odd Couple in 1968 — a role he'd already originated on Broadway, winning a Tony for it. He won the Academy Award for Best Supporting Actor for The Fortune Cookie, and later played the exasperated coach of a hapless Little League team in The Bad News Bears, the hangdog face and weary timing that defined his comedy carrying him well past the awards.