Paramount's Famous Studios division had stopped making Superman shorts, but still held the rights to the license. To that end, they decided to pit the Man of Steel, or an unreasonable facsimile, vs. Popeye. Obviously, you know how this is going to end.
Olive (Mae Questel) is poring through an issue of Superman when Popeye (Jack Mercer) shows up without bothering to knock, bearing flowers. However, he finds that Olive's tossed him aside pro tempore for her four color crush. That allows Bluto (Jackson Beck) an opportunity to put one over on both of them. He shaves off his mustache & beard and dons a padded costume to impersonate Superman, just to impress Olive. Ironically, Beck was also the narrator of the Adventures of Superman radio show, and would reprise that gig when Filmation landed the franchise more than 20 years later. In fact, he was the only cast member still at Paramount when "She-Sick Sailors" was made in 1945.
Another quick fact: co-author Otto Messmer is better known for his association with another cartoon icon----Felix the Cat!
Here's "She-Sick Sailors", which might be a big reason why Norm Crosby relied so much on malaprops as part of his act, considering how Popeye and Olive fracture the English language this time around........
In order for a "rematch" to happen, DC would have to talk to IDW, which had the last comics license for Popeye, but given how they gave Superman more of an anti-social attitude when they started the New 52........!