Yesterday's question asked for a film that starred two of the nine men who have won the Academy Award for Best Actor twice, and was made after both men had won their second Oscars. First, here is the list of the nine two-time winners:
The only film that meets the criteria is Inherit the Wind, starring Spencer Tracy and Frederic March as fictionalized versions of Clarnece Darrow and William Jennings Bryan, the opposing attorneys during the famous Scopes Monkey Trial of 1925. The film was released in 1960.
The only films I could find which starred two of these men, at any time in their careers, were Design For Living (1933), which starred Frederic March and Gary Cooper before either of them had Oscars, and The Missouri Breaks (1973) a western starring Marlon Brando and Jack Nicholson. Nicholson won his first Oscar two years later. Nicholson also starred in The Pledge (2001) which was directed by Sean Penn, but Penn did not appear in the film and in any case had yet to win any Oscars.