Origin in Thimble Theatre
Thimble Theater was a popular and well-respected serial comic strip that combined adventure, whimsy, burlesque humor, an unadorned yet poetic style, and honest insight into human nature. It originally centered on two comic schemers, Castor Oyl and Ham Gravy, and Castor's sister Olive, the voice of reason almost always ignored.
Olive Oyl first met Popeye when the sailor was hired by her brother Castor Oyl for another of his get-rich-quick schemes. After a while, Olive and Popeye fell in love with each other. In the original Thimble Theater comic strips, Olive played the role of "only sane person": she was usually the ignored voice of practical reason, first for her brother Castor Oyl and his best friend Ham Gravy in their various doomed schemes and later for Popeye, who had a tendency to fall for passive-aggressive tricks and emotional manipulations that Olive could see right through. It was not until the animated features that Olive's depiction changed to the then-popular stereotype of the fickle and unreasonably demanding girlfriend.
Olive Oyl is skinny in a comic strip in which almost of the female characters are skinny; it is never made clear whether almost all the women in Thimble Theater are comically tall or almost all the men in Thimble Theatre are comically short. Her tightly wound hair, drab flat skirt, and big feet would have been a signal to comic strip readers of the time that Olive should be understood as a comedic female character as opposed to the more common image of the sexualized female. This comedic status gave creator Segar the opportunity to develop more character depth in Olive Oyl than was common at the time in a female character.
Origin in the Cartoons and Popeye Comic Strip
People are most familiar with Olive Oyl from the Popeye cartoon created by Fleischer Studios and produced by Famous Studios. In these cartoons, Olive Oyl causes most of the fights between Popeye and Bluto. She keeps getting kidnapped by Bluto, after which Popeye has to rescue her.
No official explanation is ever given for how Olive and Popeye met or how they fell in love.
Much of the cartoon's humor comes from exaggerating Olive's long limbs, to the point she occasional appears to have the superpower of elasticity. Popeye once said she had perfect measurements 19-19-19.
Olive Oyl was created by Elzie Crisler Segar in 1919 for his comic strip called Thimble Theater, which he later changed to Popeye after he became the most popular character in the comic. Olive Oyl was a character in the comic 10 years before Popeye came into it.