Year: 1952

Classic shirt maker Van Heusen was par for the course with its ad campaigns back in the caveman days (a.k.a. the '50s): one popular series of ads featured a man spanking his wife while wearing a crisp button-down that simply refused to wrinkle no matter how hard he beat his spouse. Another campaign featured a selection of men and their preference in button-down shirts: the kicker being that the evil-looking African witch doctor loves Van Heusen, while the blonde-haired guy prefers Brooks Brothers. OK, we get the joke, and it's tasteless through and through.