In 1959's THE FIVE PENNIES, Danny Kaye plays noted jazz musician Ernest Loring "Red" Nichols. The real Nichols appears briefly in the picture as one of the "Clicquot Club Eskimos," in a sequence in which Kaye, as "Nichols," appears on a number of radio shows, singing "(Back Home Again in) Indiana" in various styles.
In 1980's THE HUNTER, Steve McQueen plays real-life bounty hunter Ralph Thorson. In one scene, McQueen, as Thorson, goes into a bar, and the bartender tells McQueen that a friend of McQueen's has died. The bartender is played by the real Ralph Thorson.
James Franco in The Disaster Artist, playing eccentric filmmaker Tommy Wiseau, has an appropriately bizarre aside with a random partygoer named Henry, who is portrayed by the real Tommy Wiseau.