Not exactly "cool" but my Dad had some odd second cars over the years. They were always inexpensive; a VW Beetle would have been an extravagance for him.
I believe when I was little he owned two Crosleys. Crosley was a Midwest auto manufacturer who made very small cars -- bordering on microcars -- in the 1940s and early 1950s. They were pretty conventional in terms of front engine, RWD -- just tiny. Curb weight somewhere in the 1200-1400 pound range. Four cylinder 724cc engine.
My memory is fuzzy on the body style; I think he had a wagon; bought used of course. Crosley went out of business in 1952.
In later years, he had a Morris, a couple of Fiat 600Ds and a Renault Dauphin. He never could stretch to get a VW. After he retired from the Navy in 1968 and became a cattle rancher he had a pickup, of course.
https://en.wikipedia.org/wiki/Crosley