#4 Shawn Michaels
For the number four spot on our most winning-est Hell in a Cell match participants, we have one of the most celebrated and decorated superstars in WWE history. He thinks he's cute, he knows he's sexy, and he's got the looks that drive the girls wild.
Shawn Michaels was there at the beginning. He battled the Undertaker in the first-ever Hell in a Cell match, held at Bad Blood in 1997. Shawn Michaels, as is his reputation, did the majority of the 'bumping' for the match. Basically he allowed the Undertaker to pound him mercilessly everywhere, even throwing the Heart Break Kid off of the satanic structure.
Michaels has managed to win the Hell in a Cell three times in four appearances in the event. It takes a legend to have a legendary record in the Hell in a Cell match, and that's just what Shawn Michaels is.