[DataKing]

I too am having a hard time coming up with a single actor who portrays two different characters that I would consider "iconic." There are a number of actors with one iconic character (Mel Gibson as Riggs, Al Pacino as Michael Corleone), but two have two separate ones does appear to be a bit of a rarity. Then there are those actors who I don't feel have individual iconic roles, because they actually overpower the characters that they portray (Nicholson comes to mind).

The closest I can come up with (and props to whoever mentioned it first) is Clint Eastwood as Dirty Harry and The Man With No Name. Dirty Harry is definitely an iconic character, and I think the second qualifies as well, though perhaps only tenuously (since no concerted effort was ever made by Leone to show that it was indeed the same character from one movie to the next).

That's my take, anyway.

Edit: Actually I'd have to agree with Stallone as well. Rambo and Rocky are definitely both iconic characters (even if some of the movies they were portrayed in sucked).