Originally Posted by
ChrisIII
Regarding Connery and Skyfall-we do have Connery to thank somewhat for the Scottish finale in the first place-Although initially not too pleased with the casting (Connery by the point he started doing Bond had been mostly known for small roles, modeling, and musicals), Bond's creator Ian Fleming warmed to the portrayal when he saw the films, and included Bond's Scottish ancestry in his last few books as a nod to Connery.
However, as for Connery in Skyfall, Connery pretty much quit acting over a decade ago with the exception of two voice over roles (Bond one last time for the From Russia With Love video game, and the weird Sir Billi/Guardian of the Highlands CGI movie). I think in part it was due to his bad experiences on the set of The League Of Extraordinary Gentlemen that prompted his retirement (Plus he's always been fairly difficult to work with anyway). He was also offered to return as Indy's father in Kingdom of the Crystal Skull but refused (due to his retirement) It's speculated by some that the Harold Oxley role was originally meant for him (as Henry Jones sr).
As for Brosnan as Silva, I doubt that would have worked out anyway. Pierce wasn't too pleased that he was kind of fired so they could reboot and cast Craig, so he probably wouldn't be too happy working for the producers again.