5) Batman vs Iron Man - The ultimate rich kid brawl. The world's greatest detective matching dollars and gadgets with the industrialist playboy. I think Tony Stark would have the upper hand at first due to superior fire power but in the end I see Bruce as the victor. Given time, he would find the proverbial chink in the armor.
4) The Punisher vs Rorschach - Head to head psychotic vigilantes. Walter and Frank share an adherence to violence as a necessary evil, making for a gory bout. After a long, grotesque battle in which blood and possibly limbs would be lost, I see Frank walking out alive.

3) Spider Jerusalem vs Dwight McCarthy - The anarchist writer against the nihilist photographer. A gritty urbanite fight to the death. Dwight's dark brooding chivalry matched with Spider's unhinged hatred for all humanity. Bullets, blood and a disrupted bowel later, I see Spider standing winner with his filthy assistants.
2) Joker vs Delirium - Crazy is as crazy does. Packing that much insanity into a comic book probably has rules and regulations against it, but damn it I want to see it. While Delirium is not known for fighting prowess, her vast powers as one of the Endless would enable her to turn Mr. J into a potted flower or something along those lines.
1) Superman vs The Saint of Killers - The title fight of the century! The Man of Steel in a duel with the Angel of Death. Supes would put up a good fight - shooting eye beams, using super breath, hurling large objects, etc. But in the end the Saint would just get pissed and gun down the red and blue boyscout.
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