6. A Gay Time In Prison With The Joker
Much of Batman's dialogue in his early adventures can now be read in a way which instantly embarrasses the hero, but perhaps one of the worst came when he sent arch enemy The Joker a Christmas greeting wishing him a Gay Time In Jail. Obviously that word once meant happy, but seeing as he's referring to jail at the same time, you have to wonder if Batman's message had a slightly more sinister intention. Needless to say, if Batman couldn't see how this could be misinterpreted, he ends up looking very silly indeed in this particular case.