I am hoping that the teeming millions might be able to help me discover the etymology of the use the word “square” to mean cigarette. I belive it to be primarily an AA (African-American) expression. The earliest usage that I can find is on Aretha’s 1968 recording of “your a sweet man” where she sings “gotta stop right there, gotta have me a square”, but it certainly predates this usage…thanx to all!
According to the OED, it means a cigarette conatining tobacco rather than marijuana and is related to “square” meaning a conventional or old-fashioned person. This is, in turn, related to “square” meaning honest or straightforward as in “square deal”.
Thank you Tom H!