The Despicable Deadpool: What’s So Entertaining About Pain?

When I returned to comics in 2015, one of the first trades I read was Brian Posehn and Gerry Duggan’s hardcover collection Deadpool (Vol. 1), containing the first twelve issues of their run going back to November 2012.  It was a Christmas gift from Kalie and my first real experience of the Merc with a Mouth, outside of occasionally seeing him as an X-Force villain back in the ‘90s.  I was instantly in love with the character!  Posehn and Duggan’s take became the primary lens through which I view the Regeneratin’ Degenerate.  With The Despicable Deadpool #300, Gerry Duggan ends his five-year run on the title.  Over the years the tales have gotten darker and darker, as he’s broken Wade Wilson to a painful degree.  As I read these stories my heart hurts, and I can’t help but wonder why do we partake in stories where the characters we love are damaged so severely?