8. Deadpool: Sins Of The Past
With Deadpool being a sleazy, creepy, gross kind of character in his early days, it's fair that his second miniseries writer, Mark Waid, felt less than entirely comfortable over detailing the character's questionable exploits, as was uncovered in an interview he had with Wizard magazine in 1997.
While this seems bizarre now - as Deadpool is arguably more a genuine hero than an anti-hero most of the time in modern comics - back in the day, he was capable of some pretty reprehensible things. And although it's not as though Waid writing Deadpool in character was him saying these things were okay, it is understandable that the writer was perhaps uncomfortable with trying to get into the mercenary's mindset, as Deadpool has experienced some considerable character development since this time.
Sins of the Past is arguably one of the first Deadpool comics that any fan needs to read in order to understand the character. However, seeing this much colder crueler version of Deadpool, it's readily apparent why Waid may have not enjoyed working on series as much as we may enjoy reading it.