Image consultant to history's greatest monsters
You know what actually would have made Saddam Hussein pretty cool? If, when the US put out that deck of cards featuring all the top Iraqi government figures, he had totally embraced it and made the ace of spades his new gimmick. He could have started using Motörhead's "Ace of Spades" as his personal theme music, either making elaborate Triple H-style entrances to the classic heavy metal anthem, or just having Paul Shaffer and the band play him out to an instrumental version whenever he appeared on Letterman (being a frequent Letterman guest would have made him cooler too, naturally). The lyrics would have even fit him, expressing bad-ass defiance in the face of his eventual defeat by American forces:
You know I'm born to lose
and gamblin's made for fools
But that's the way I like it baby
I don't want to live forever
Also, if he had to keep killing people, he could have left an ace of spades turned up on top of the body, as a personal calling card. Then he would have been like a Batman villain.