My post yesterday about the ugly "Get Out of Jail Free" card in the recent version of Monopoly led to an interesting discussion in the comments. The conversation steered in the direction Monopoly's awful gameplay. I can't argue with that. An even worse game, though, is Battleship. (Cracked has a good takedown of Battleship, along with Monopoly, Risk, and other popular boardgames.) I used to have the version of Battleship above. When I was a kid I thought it was funny (in a mean way) that the mom and girl were doing dishes while the dad and son were whooping it up in the next room. But as an adult, it strikes me just how horrible it is. Carla says this cover depresses her in the same way this 1956 "Busy Day" Jello commercial does.
Sexism still exists of course, but I don't think a major game company would make something so overtly sexist today. Feel free to prove me wrong in the comments.