Green’s Dictionary of Slang

1. (US) an automobile.

1954

‘“Hipster” Rev. Dict.’ Mad mag. Oct.

2. (S.Afr.) a homeless young street beggar; thus strolling n. [note Scot. stroller, a vagabond].

1987		L. Beake Strollers 1: A stroller is someone who don’t sleep by his house. He don’t eat by his house – he eats by the bins. A stroller is someone who thinks he is free. [...] Why don’t you come with me, man? I’m going strolling. [Ibid.] 38: It was one of them what started it – the Spider Men. Wanted us to be lighties, you know, join the gang. Well we didn’t want to! We like strolling, man, not running errands for a bunch of [...] ‘diefs’.
2004		Social Services in a Changing S. Afr. 166: Sometimes we say we are the ‘Malalapipe’ because we sleep in the big pipes there where they are making the buildings. In Afrikaans the name for these children is ‘skadukinders’, in the Cape they call themselves ‘strollers’.

3. (US black) an itinerant street musician.

1971

B. Short (con. c.1935) Black and White Baby 139: [W]hat were known in those days as ‘strollers’—musicians who played portable instruments, accordion or guitar.

4. see stroller under stroll n.