While many of the earliest wristwatches included decorations on their faces, what we now know as the character watch was a uniquely 20th-century invention. Generally featuring cartoon characters, these watches were produced to capitalize on franchises from comics, films, and television.

The first watch to feature a cartoon character was a pocket watch designed in 1908 by Ingersoll, which depicted the Buster Brown comic strip character promoting Blue Ribbon Shoes. Most character watches followed in this format, incorporating a static painted face plate mounted behind a normal-looking mechanism, though their design was trumped in 1933 by the animated style of the Ingersoll-Waterbury Mickey Mouse watch. These watches depicted Mickey’s yellow-gloved fingers rotating on wiry black arms, and resulted in the most successful character watch ever.

Even so, their animated quality was soon outdone by the New Haven company with its 1934 Popeye watches, whose entire hands were shaped like the tattooed sailor’s arms, making Popeye seem to flail about in mid-stride. Around the same time, New Haven also released watches featuring the likenesses of other kid-favorites, like Superman, the Lone Ranger, Dick Tracy, Little Orphan Annie, and Smitty. Ingraham jumped in with Betty Boop and Buck Rogers, and the industry continued to boom until factory restrictions were imposed during World War II...