The Merc With The Mouth
VS
That Bitchy Goth Guy
I think they would get on each other's nerves so much that the whole thing would seem more like "The Mask Vs Lobo" than anything else. Picture the scene, two battered, blood and bleeding warriors, Deadpool with a pair of pliers ripping out Dante's teeth while Dante plays Cat's Cradle with Deadpool's intestines.
Ridiculous, but awesome.