The Simpsons: 10 Guest Spots That Almost Went To Someone Else
3. James Woods in “Homer and Apu”
Season 5's "Homer and Apu" is a great episode, but it wouldn't be half as great without James Woods. The voice of Hades is a total tour de force as Apu's replacement at the Kwik-E-Mart, hitting every single one of his beats perfectly and carrying the entire subplot of the episode basically by himself. It is, quite frankly, astonishing how Woods managed to pull this off, especially when he wasn't even the writer's first choice.
Of all people, Sir Michael Caine was actually the prime target for this role. The star of The Italian Job and Dark Knight trilogy would have also been in Springfield researching a part in a future movie, although it is unclear whether Sir Michael's role would also have been changed to that of "Inuit Firefighter".
Caine turned the role down and Woods was then asked to take it on, and thank God he did. James Woods is one of the finest guest stars The Simpsons has ever had and, whilst Michael Caine is a great actor, it's hard to imagine him coming remotely close to what Woods pulled out of the bag here.