Youd think the worst for ol Frankie would be over after the Archie debacle, but sadly the worst was to come. Probably even more unfortunate was the worst for the Punisher wasnt being killed by Wolverines emo-raging son and turned into a Frankenstein-like monster for a year, or even being thrown into space and having to well be The Punisher in space. No, Frank Castles worst hour came during a team up with the Real Slim Shady. In 2009s Eminem and The Punisher, the titular rapper and anti-hero team up to take on the B-list assassin Barracuda. What resulted was a one-shot that served to be nothing more than a phallic extension device for Mr. Mathers. Whether hes pistol whipping and murdering Punisher look-a-likes or saving the superhero by eviscerating a contract killer with a chainsaw, Eminem and The Punisher seemed to exist solely to appease Eminems superbly grand ego at the expense of The Punishers masculinity. Its a shame, because such a crossover teased the possibility of The Punisher murdering Eminem, which would have made a far more entertaining story. Content for future fan fiction, I suppose.