Retronaut unearthed a couple of weird 1930s ads for Virginia Rounds (grandmother brand to Virginia Slims), a cigarette by Benson & Hedges aimed at women.
The example above, with its sharable dark humour and user-generated content contest, isn't that different from "breakthrough" social media campaigns today. (Although the disregard for the baby's health would also create a massive social media PR meltdown in today's more sensitive media era.)
The campaign also used celebrity. Illustrator Russell Patterson was a legend, having helped define the flapper style in his 1920s cover and interior artwork for publications like The Saturday Evening Post, Vogue, Vanity Fair, Cosmopolitan, Redbook and Photoplay. He was also a successful syndicated cartoonist.
The dated, but interesting, "girl power" approach in the ad above foreshadows Virginia Slims' 1960s pseudo-feminist marketing strategy of "You've come a long way baby". And like it, it commits the unforgivable crime of co-opting female empowerment to sell a deadly product.
I found one more ad from the series at tobaccodocuments.org: