Shemals — Cartoon

However, it's worth noting that, the earliest and most notable example of a cartoon shemal was a character created by the legendary cartoonist, Max Fleischer, named 'Bosko'. Created in the late 1920s, Bosko first appeared in the cartoon "Sinkin' in the Bathtub" (1929) and was followed by a series of shorts featuring the character, often paired with his on-again, off-again girlfriend, Honey. Bosko was depicted as a shemal due to his ambiguous appearance, often sporting a mix of masculine and feminine features, such as a slender build, feminine facial features, and a high-pitched voice.