In the 1920s Guinness had a problem. The venerable Irish brewer had been around since 1759—nearly two centuries—but geopolitical events were threatening to render its sales flat. Irish independence had leveled a new import tax on England-bound barrels. Add this to the near total loss of a prohibition-era U.S. market and things were not looking good for the sultan of stout. Guinness needed a marketing strategy—a relatively new concept at a time when legacy brands saw advertising as desperately uncouth. The in-house tagline “Guinness is good for you” was born in 1929 (the first of many touting the beer’s health benefits) but it wasn’t until Guinness tapped London creative agency S.H. Benson that the brand’s first legendary ad campaign would begin. Illustrator John Gilroy was given the account.

Gilroy, a former cartoonist for the Newcastle Evening Chronicle, transformed Guinness’ image from town drunk to safari satire by incorporating simple, effective slogans into his trademark animal illustrations. In a Draper-esque moment of clarity, Gilroy, on a trip to the circus, noticed a sea lion balancing a ball on its nose. His Eureka moment was replacing that ball with a pint of plain.

Gilroy sketched mock adverts for a planned Guinness expansion to Germany in 1936. (John Gilroy/Guinness/S.H. Benson)

The campaign was a hit, and Gilroy continued to pump out illustrations for the pint powerhouse into the 1960s. Most of his animal ads are now universally recognized—the toucan having risen at least to the level of the Irish harp in the echelon of Guinness logos.

Lesser known, however, are the campaigns Gilroy mocked up for Guinness that never ran. One, intended for the German market in 1936, incorporated Nazi insignias with translated versions of classic Guinness slogans. (My goodness, mein Guinness, anyone?) Another product-placed glasses of stout into masterworks from art history—a touch of oddball humor which feels on par with some of today’s beer marketing strategies. One rare series from the 1940s are a hard pitch at wartime morale, with feckless sailors and overworked mechanics finding their way through tough times with the promise of a comforting—and energizing—pint of the black stuff.