Casting What-Ifs
Castle Rock wanted Brad Pitt and Leo as Will and Chucky; Mel Gibson was attached to direct; Jeff Bridges or Dustin Hoffman imagined as Sean; Michael Mann wanted to direct the pair as car thieves and replace Damon
In the discussion (4)
Approx. transcript time · 00:38:01Read transcript
- Castle Rock wanted to replace Matt and Ben with Leo and Brad, and Mel Gibson producing and directing would have been weird.
- Nobody else seems to have been seriously considered for Sean until the tail end; there is an argument that Williams is more replaceable than Damon and Affleck, yet the movie is completely different with Jeff Bridges or Dustin Hoffman, and nobody else gets the community college bit about Freud doing cocaine, which must have been freestyled from his 70s stand-up.
- After Gibson dropped out, Michael Mann wanted to direct, making the two slightly different, as car thieves; he also wanted to replace Matt Damon, which is why it went no further; the hosts joke about James Caan or a Hemsworth and tell Mann to buy the rights and remake it.
- Earlier context: at Castle Rock the roles were at one point meant for Brad Pitt and Leo in a twice-as-long script whose second half had Chucky and Will on the run from the CIA; Mel Gibson was attached and developing it after Braveheart, and the writers asked him to let them have it back because they needed to make it faster.