"She-Sick Sailors" (1944) opens with shots of Olive Oyl reading Superman comics and swooning over the superhero's image. Popeye comes by for a visit and Olive puts him off for interrupting her comic book reading. Bluto happens by and overhears Olive pining for Superman, so he bursts onto the scene, newly clean-shaven, in a Superman costume. When Popeye protests, Bluto promptly throws Olive out the high-rise window and challenges Popeye to rescue her. Bluto has his own rescue plan, though, and he and Olive laugh at Popeye's failed attempt. So it goes, Bluto battles Popeye over Olive's affections until Popeye gets a burst of super power in his own time-honored fashion and shows Olive who the real superhero is. There are a few good gags on Bluto's part, including the ingenious way he uses a commuter train to "prove" his super-strength, but for a cartoon match between Popeye and "Superman," there should have been a little more effort made throughout. The story is credited to Bill Turner and animation pioneer Otto Messmer, who was recognized late in life as the genius behind the silent-era Felix the Cat. (Check out John Canemaker's documentary, "Otto Messmer and Felix the Cat.")
The depiction of Superman in the comic book Olive reads is quite unusual. The images certainly match what we know of the Superman comics of the era, but the dialogue balloon we see has Superman say, "Now to foil the dastardly curs and rescue the fair damsel," an odd and archaic turn of phrase to put into Superman's mouth, but one presumably guaranteed to appeal to Olive. Interestingly, when Bluto first appears as Superman in Olive's apartment, his blue costume has a red "S" on the front. When he leaves the apartment, and in all subsequent scenes, the "S" is gone. Curiously, in the opening credits, there is no mention of Superman or any acknowledgment of the rights owner. This cartoon was made a year or so after the last theatrical Superman cartoon short, "Secret Agent" (also reviewed on this site), was made by Paramount/Famous Studios, which also produced this cartoon. It's doubtful the studio still held the rights a year later to use the character in a cartoon. Even the Superman cartoons they made carried an acknowledgment: "By arrangement with Action Comics and Superman magazines/Superman comic strip created by Jerome Siegel and Joe Shuster." I would think some mention would have been required in this case also.
The depiction of Superman in the comic book Olive reads is quite unusual. The images certainly match what we know of the Superman comics of the era, but the dialogue balloon we see has Superman say, "Now to foil the dastardly curs and rescue the fair damsel," an odd and archaic turn of phrase to put into Superman's mouth, but one presumably guaranteed to appeal to Olive. Interestingly, when Bluto first appears as Superman in Olive's apartment, his blue costume has a red "S" on the front. When he leaves the apartment, and in all subsequent scenes, the "S" is gone. Curiously, in the opening credits, there is no mention of Superman or any acknowledgment of the rights owner. This cartoon was made a year or so after the last theatrical Superman cartoon short, "Secret Agent" (also reviewed on this site), was made by Paramount/Famous Studios, which also produced this cartoon. It's doubtful the studio still held the rights a year later to use the character in a cartoon. Even the Superman cartoons they made carried an acknowledgment: "By arrangement with Action Comics and Superman magazines/Superman comic strip created by Jerome Siegel and Joe Shuster." I would think some mention would have been required in this case also.