1. Wolverine
Was Wolverine based on Clinty? I think he probably was but I'll leave that to someone more knowledgeable than myself to fill us in on (comments bellow). Over the years Logan has gone through patricide, world wars, samurai lifestyles, being torn limb from limb and even growing old as hell (took long enough). No matter which point in Wolverine's long and fruitful campaign of bad-assery you look at, Clint Eastwood is perfect for the role. All it took was a bit of stubble and a cigar to turn Rowdy Yates into the man with no name. Think what full on side burns and metal claws would have done! Wolverine is such an obvious fit because the character is so similar to Clint's on screen persona but what would have made it really special is how genuine it would have been. Hugh Jackman is pretty good in fairness (and if you check out some of Clint's early work, you'll notice they are strikingly similar looking) but he lacks the natural squint and gravely voice. Jackman has to put it on, it's never the same. For me the ultimate point in Wolverine's career for Clint to portray would be his twilight years, looking about 60 (but being a few hundred years old) as Clint would still have been fit enough to kick ass (he was fit enough for that in Gran Torino) and also Wolverine would have all that life pressing down on him.
