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Donald Duck is known for many things, including being one-third of The Three Caballeros alongside the likes of Panchito Pistoles and Jose Carioca. But that film was hardly the first time that Donald donned a sombrero – in fact, a 1937 Silly Symphonies short called Don Donald preceded it by several years.

Don Donald stars the titular duck as he rides a temperamental donkey through the desert on the way to see his girlfriend, Donna Duck. After Donald and Donna have a bit of a spat, Donald upgrades his ride by getting a car at a local trading post, which helps win Donna back. However, the car encounters engine issues and breaks down in the middle of the desert. After further hijinks, Donna bails on Donald (riding away on a unicycle that she happens to carry with her in her purse), and Donald ends up alone with his original steed in the end.

Despite featuring Mickey Mouse’s face at the beginning of the cartoon, the short was actually the first installment of the Donald Duck series for Disney, as it was the first to feature Donald as the primary starring character. Though Donald would later end up with Daisy Duck as his lady love, this also marked the first time a love interest was introduced for him in the form of Donna (who would later be retconned into being Daisy’s rival in a 1950s comic strip). Donna would later appear in the British Mickey Mouse Weekly magazine, but would never appear in another Disney cartoon.

Hake’s Auctions currently has a page of Don Donald artwork in their current Auction #227. Disney had an arrangement with Good Housekeeping magazine from 1934 to 1944 in which Disney’s animated shorts were promoted. This particular painted artwork by Tom Wood features Donald and Donna over the course of four panels – Donald arriving on his burro, playing guitar and giving Donna flowers before things go a bit sideways from there. The artwork is framed and ready to display, and is an excellent representation of one of Donald’s earliest appearances. This auction will close on Thursday, July 11, 2019, and interested collectors are encouraged to submit their bids soon.

For more on the history of Donald Duck, find an in-depth feature in celebration of his 85th anniversary elsewhere on Scoop.