An archetypal setup from the earliest weeks of "Thimble Theatre", featuring Olive as a damsel-in-distress and Willie Wormwood and Harold Hamgravy as competing suitors
An early example of Olive's exasperation towards Ham Gravy's "cheapness" (July 7, 1920)
Segar frequently utilized Olive's abysmal baking abilities as a staple of the early strip's comedy (February 14, 1921)
One of multiple early strips emphasizing Olive's disastrously awful singing (March 30, 1922)
Another indication of Olive and Ham's comic dysfunctionality (May 30, 1922)
Olive displays her physical combat prowess to Ham (July 15, 1923)
Olive, Ham and Castor opportunistically offer to "guard" and organize a millionaire's reserve of wealth (March 15, 1925)
Thimble Theatre, August 25, 1925
Ham and Olive as children in 1907 (February 4, 1926)
Thimble Theatre ad (July 11, 1926) featuring Olive
Olive engages in contemporary flapper fashion trends (March 30, 1926)
Olive and Ham feign stereotypically "idealized" appearances, much to Castor's incredulity (April 1, 1926)
Olive Oyl with her sister-in-law Cylinda (February 5, 1927)
Olive, following months of absence, reunites with an unexpectedly-bedraggled Ham (July 11, 1928)
Olive dons a "foolproof" disguise to investigate Ham's wavering loyalty (August 4, 1928)
Olive stows away on Castor and Ham's ship to
Dice Island, thus leading to her earliest encounter with Popeye within the daily strip (January 25, 1929)
Ham discovers Olive's affair with Popeye, thus marking the end of their longtime relationship (March 2, 1930)
Popeye indirectly professes his attraction to Olive within the Glint Gore storyline (March 1931), foreshadowing the beginning of their relationship within the daily strip's continuity