Well, he probably didn’t drink bourbon. Most historians agree that he probably avoided alcohol save for the occasional glass of wine or beer. I did a double take, however, when I saw Hitler’s doppelgänger getting served Walker’s DeLuxe on the rocks in this classic ad.

I’ve come across quite a few vintage whiskey ad head-scratchers. Some are simply outdated — chauvinism and even racism aren’t uncommon. Then there are some ads that are just bizarre. This one appeared in Life Magazine in 1957, and that little tiny mustache and combover surely would have been noticed by the Greatest Generation, tweed jacket notwithstanding.

Image courtesy of the Gallery of Graphic Design