Ok, I'll bite:
(turns out it was easier than I thought, just like my previous challenge!)
Salvador Dali -->Father of the Bride(designer for this one, believe it or not) -->Elizabeth Taylor -->Peter O'Toole (Under Milk Wood) -->Sean Bean or Orlando Bloom (take your pick
)
or if you consider Troy not yet released (but still very soon to come):
Liz Taylor -->Paul Newman -->Kevin Costner (Message in a bottle)-->Elijah Wood (The War).