9. That Time He Wore Blackface
Yep, what you're seeing is real. When was it released? 1991. Nineteen. Ninety. One.
In the storyline, Frank Castle - everyone's favourite perennial fugitive - is on the run and in need of a change of identity. Seeking out a disgraced surgeon, Castle goes under the knife and emerges as a black man, with writer Mike Baron using the opportunity to team Frank up with Luke Cage in some bizarre blaxploitation story-arc.
The storyline was as cringe-inducing and insensitive as it sounds, and Baron was taken off the book shortly after. As for Castle? The procedure soon wore off and he hit the road again, probably in search of a better creative-team.