Hey, I have a good one that I’m surprised hasn’t been mentioned yet:
Played by Alec Baldwin, Harrison Ford, Ben Affleck, and Chris Pine.
Baldwin was in “Working Girl” with Harrison Ford.
Baldwin was in “Rise of the Guardians” with Chris Pine (both with major voice roles)
Baldwin was in “Pearl Harbor” with Ben Affleck
Affleck was in “Smokin’ Aces” with Pine.
Ford has nothing with either Affleck or Pine.
Robert De Niro and Jack Nicholson both appeared in The Last Tycoon.
De Niro played Satan in Angel Heart.
Nicholson played Satan in The Witches of Eastwick.
Back to Wyatt Earp…
Kurt Russell played Wyatt Earp in the great Tombstone.
Kevin Costener played him in the not-so-great Wyatt Earp.
They both played armed robbers in 3000 Miles to Graceland.
There’s a third! Donald Pleasance was also in The Greatest Story Ever Told, as Satan. And he played Blofeld in You Only Live Twice.
Now that’s impressive! A threefer!
This one hasn’t quite happened yet, but Ian McKellan will be playing the aged Sherlock Holmes in an upcoming movie, and he and Benedict Cumberbatch’s voice appear together in The Hobbit.
Christopher Eccleston and David Tennant were in the 1996 Jude. The were respectively Dr. Who ten and nine.
In the upcoming Michael Bay Teenage Mutant Ninja Turtles, William Fichtner plays Shredder. In the original theatrical version, the role of Shredder was played by James Saito. They both appear in Pearl Harbor.
ETA: Mako was also in Pearl Harbor, and voiced Shredder in the 2007 TMNT.
*Withnail and I *starred Paul McGann and Richard E.Grant.
PM was the official 8th Doctor Who. REG was an unofficialDoctor. Actually, twice.
Bernie Casey also had the lead in a remake of Get Carter. But I’m surprised to see that despite his long career, Casey has never been in a movie with Caine or Stallone.
Jude Law tried to follow in Michael Caine’s footsteps as Alfie before co-starring with him in the remake of Sleuth – playing, of course, Caine’s old “Milo Tindle” part.
Bryce Dallas Howard played Gwen Stacy in Spider-man 3.
Emma Stone played Gwen Stacy in The Amazing Spider-Man (and it’s sequel).
They were both in The Help.
The Hunger Games: Catching Fire has Philip Seymour Hoffman and Toby Jones, who both played Truman Capote–Hoffman in Capote (2005), Jones in Infamous, released a year later.
If TV movies count, Patty Duke and Melissa Gilbert have both played Helen Keller in The Miracle Worker, and have been in more than one TV move together, including the Gilbert version of The Miracle Worker, where Patty Duke played Annie Sullivan. So, that means that Anne Bancroft and Patty Duke have both played Annie Sullivan, and appeared together in the version of The Miracle Worker with Duke as Helen Keller.
Family of Strangers and* Touch of Truth* are at least two of the other TV movies Duke and Gilbert did together. All disease-of-the-week type stuff.
Patty Duke is so talented, and so lousy at picking good scripts.
Morgan Freeman and Gene Hackman appeared together in Unforgiven.
Morgan Freeman played God in Bruce Almighty.
Gene Hackman played God in Two of a Kind.
Josh Brolin spent MEN IN BLACK III doing a dead-on Tommy Lee Jones impression sure as they were both in NO COUNTRY FOR OLD MEN.
Frank Welker and Leonard Nimoy both provided the voice of G1 Galvatron, both were in Transformers: Dark of the Moon.
The Rock stars as HERCULES this month, forty-five years after Schwarzenegger was HERCULES IN NEW YORK, with them meeting in THE RUNDOWN along the way.
Dennis Quaid and Stacy Keach have played Sam Houston, and were also in The Long Riders.
Here’s an odd one… Val Kilmer played Doc Holiday in Tombstone (with Kurt Russel as Wyatt Earp), but then Kilmer went on the play Earp is a straight to video flick called Wyatt Earp’s Revenge
Both Randy and Dennis Quaid played Doc Holiday, and both were in The Long Riders.
Richard Harris played King Arthur in CAMELOT, as did Sean Connery in FIRST KNIGHT, and they both appeared in ROBIN & MARIAN – with Harris as Richard the Lionheart long before Connery got around to doing it when Costner played Robin Hood.