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I am a big fan of the Legend Killer gimmick as well so I had to vote for Orton. HBK was excellent as a heel but I really liked how Orton's character evolved.
Big mark of The Legend Killer gimmick/evolution days and then his heel run a few years back when he got involved with the HHH/McMahon family and RKO'ing Stephanie then kissing her right in front of HHH. Great work from Orton so he gets my vote.
As great as the Lengend Killer was I don't remember him ever getting the kind of heat which HBK did in DX or even at the start of the HBK run. This is pretty one sided to me, Michaels all the way.