When David Smart, Henry Jackson and Arnold Gingrich published the first issue of Esquire in Oct 1933 they included fiction by Ernest Hemingway and Dashiell Hammett, sports instruction by Bobby Jones and Gene Tunney and a full-colour cartoon by George Petty. Petty’s airbrushed cartoons – essentially excuses to draw barely-dressed women – became, not surprisingly, the most popular feature in the magazine. Beginning with the Dec 1939 issue the “Petty Girl” was enlarged into a gatefold and the modern magazine pin-up was born.
By this time Petty’s relationship with the magazine was wearing thin and in 1940 he was replaced by Alberto Vargas.1 The next year Smart decided to take some of Vargas’ illustrations and produce a wall calendar. The Esquire Varga Calendar sold 320,000 copies and was the best selling calendar in 1941 of any kind. Over the next six years the Esquire Varga Calendar was published in many different formats including a wall calendar, a desk calendar (in leatherette!) and even a pocket-sized military calendar shipped to GIs in Europe.
January – Curtain Call, Ben-Hur Baz – February – RFD, Fritz Willis 
March – Objection, Joe De Mers – April – Bedtime Story, unsigned 
May – Predicament, J. Frederick Smith – June – Meadow Lark, Ben-Hue Baz
Vargas’ relationship with the magazine would prove even more contentious than Petty’s. He sued Esquire over his contract and he was replaced in 1947 by a rotating stable of artists including Ben-Hur Baz, Joe De Mers, Fritz Willis and J. Frederick Smith. The 1948 Esquire Glamour Gallery was their first post-Vargas calendar.
July – Endorsed, Fritz Willis – August – Maid to Measure, Joe De Mers 
September – Si, Si, Ben-Hur Baz – October – Floral Offering, Fritz Willis 
November – Exposure, Ren Wicks – December – Sawdust to Stardust, Joe De Mers
After the 1953 publication of Playboy and the popularization of the photo pictorial the pin-up fell out of favor. Esquire’s last illustrated calendar was in 1957.
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