Esquire magazine, which launched in 1933, was a precursor to Playboy in various ways. While it included substantial articles, it was mainly bought for its pin-up content. Instead of photographic nudes, Esquire’s pin-ups were alluring glamour girl cartoons, originally by George Petty. By 1939, these cartoons had developed into double-page spreads, essentially introducing the concept of the centerfold.

h/t: vintag.es

A dispute arose between George Petty and the magazine publishers, leading to his replacement in 1940 by Alberto Vargas. Vargas remained with Esquire until 1947, when he also had conflicts with the magazine’s publishers. This was unfortunate as the successful Esquire Vargas Calendar, introduced in 1941, sold approximately 320,000 copies in various formats. Later in 1957, Vargas joined Playboy, where his work continued to appear for the next 21 years.

After Vargas left Esquire, a rotating group of artists took over, creating the 1948 calendar, which ironically became the most famous. Stylistically, it closely resembled Vargas’ work (although Esquire had cleverly trademarked ‘the Vargas Girl,’ omitting the “S” from his name, resulting in Vargas losing a court case). Artists such as Ben-Hur Baz, Joe De Mers, Fritz Willis, and J. Frederick Smith contributed to this calendar.

Esquire produced calendars until 1957, when they phased them out due to the rise of new men’s magazines featuring explicit photographs.