Hamilton complained in a newspaper article about being typecast, stating "After I was first cast as a heavy on The Untouchables, I couldn't ever persuade them [producers] that I could also do something else. " While comic roles were rare for Hamilton during his Hollywood career, he had one opposite Andy Griffith in the 1958 military comedy No Time for Sergeants, as well as an appearance in Steven Spielberg's raucous comedy 1941, released in 1979. He also appeared in a comedic guest spot on Mama's Family in the second-season episode, "Mama Cries Uncle", as Uncle Roy. He was more often cast in dramatic works, such as the stark science-fiction drama Seconds (1966), which starred Rock Hudson. In two of his most distinctive performances, Hamilton appeared with Paul Newman in The Hustler (1961), playing Findley, a wealthy billiards player who gambles for high stakes, and in The Graduate (1967) as Mr. Robinson, husband of the seductress Mrs. Robinson. In 1975, Hamilton appeared again with Newman in The Drowning Pool. He also worked with Robert Redford in a pair of films, The Way We Were (1973) and Brubaker (1980). In early 1982 he appeared as a judge presiding over an impromptu court case on an episode of Bret Maverick.