I was never crazy about 97% of the Tom and Jerry shorts, PERIOD. But "Calypso Cat" is one of the few exceptions.
When I saw this short for the first time in 1988 (I was on a business trip in Chicago and WTBS ran this short; Turner Entertainment Co. had just purchased the pre-1985 MGM movies and TV shows), I noticed something familiar in the style of the animation. Then I thought, "This Tom and Jerry looks Popeye-ish!" And I later discovered Gene Deitch, who produced some of those "Popeyes" and "Krazy Kat," produced "Calypso Cat."
Especially funny was when Tom tried to warm up to the white female cat after Jerry played his pranks on Tom (she thinks twice, smiles, and gives Tom her hand, after which they walk out of the boat onto the island). And somehow, that steel drum music the other cat played is reverberating through my mind right now, as when that cat used his drumsticks on Tom's head and it sounded like a steel drum!
And, long before Billy Ocean had a #1 hit of the same title in late 1984, the boat was named the "Carribean Queen" (which, obviously, went through my mind when I saw the name; I have the original Billy Ocean album that song's on).
All told, "Calypso Cat" is a likable cure for the common Tom and Jerry cartoon. I'd give it an 8.