James Brolin and Elliot Gould were in Capricorn One.
Both have played the role of Barbra Streisand’s husband.
Brolin’s still on tour!
John Carradine played Lincoln and appeared in the following movies with these other Lincolns:
Henry Fonda - The Grapes of Wrath.
Walter Huston - Of Human Hearts.
Raymond Massey - The Hurricane
Collaborating FDR’s
Ralph Bellamy & Jason Robards: The Good Mother
Bill Murray & Alan Cumming: Garfield (both voices)
cited in post #26, and disputed in post#30.
Cate Blanchett and Judi Dench both were nominated for Oscars for playing Queen Elizabeth I (Dench won).
They were also both nominated for Oscars when they appeared together in Notes on a Scandal.
Heh. "The same thing happened to meeeee!"
The Sheens also both appear in Hot Shots! Part Deux, where they find themselves on passing Vietnam patrol boats with clashing voiceovers. They see each other and simultaneously shout, “You were great in Wall Street!”
Damon and Pepper were also both soldiers in Saving Private Ryan.
Nitpick: It’s “McKellen.”
Whoopi Goldberg and Cher both appeared in The Player.
Whoopi Goldberg played God in It’s a Very Muppet Christmas.
Cher played God in an episode of Will and Grace.
Martin Freeman and Jude Law appear together in Breaking and Entering.
Martin Freeman plays Dr. Watson in the TV series Sherlock.
Jude Law plays Dr. Watson in the movie Sherlock Holmes.
Brian Cox and Anthony Hopkins appeared together in Red 2.
Brian Cox played Hannibal Lecter in Manhunter.
Anthony Hopkins played Hannibal Lecter in The Silence of the Lambs.