Okay, let’s do this!
Pierce Brosnan was in The Thomas Crown Affair with Denis Leary
Leary was in Love Walked In with J.K. Simmons
Simmons was in Spider-Man with 1973 Oldsmobile Delta 88
Delta 88 was in Stigmata with Jonathon Price
Price was in Game of Thrones with Max von Sydow
You may have known an easier way, but I really had to research this one.
Next up: Alec Baldwin to Chris Pine and bonus points if you can get Harrison Ford and/or Ben Affleck in there as well to encompass all the actors who have played Jack Ryan. I don’t think it’s possible to get all four, but maybe someone will surprise me. Note that Baldwin and Pine have to be the first and last entries!
EDIT: Scratch that, it IS possible to get all four!