Apparently, this particular usage of blackface also isn't funny, which is odd, given the fact that this picture contains almost all of the qualities I normally look for when deciding whether or not a picture is funny (i.e. blackface, gay panic, public embarassment of elected officials, barbie dolls being given as trophies, lavendar sateen jumpers being worn in concert with lavendar frilly cuffed blouses, and overt racism).
Actual quote from the mayor: "Blackface is shoe polish. That's not what I did. I dressed up to win and because it was so hilarious."