The term "square", in referring to a person, originally meant someone who was honest, traditional, and loyal. An agreement that is equitable on all sides is a "square deal". The evolution of American culture transformed the term from a compliment to an insult to an obsolete term.
In the parlance of jazz, a square was a person who failed to appreciate the medium, hence (more broadly) someone who was out of date or out of touch. Such was the opprobrium attached to "squareness" among jazz lovers that musician Thelonious Monk adopted the middle name "Sphere". The term, with its broader meaning, has persisted and has permeated mainstream culture, as exemplified in Huey Lewis's 1986 hit Hip to be square. In ultimate self-reference, this song was later used by Sesame Street to illustrate the geometrical meaning of "square".
In the counterculture movements that started in the 1940s and took momentum in the 1960s a "square" referred to someone who clung to repressive, traditional, stereotypical, one-sided, or "in the box" ways of thinking. The term was used by hipsters in the 40s, beatniks in the 50s, hippies in the 60s, yippies in the 70s, and other individuals who took part in the movements which emerged to contest the more conservative national, political, religious, philosophical, musical and social trends. It was in this context that Sly and the Family Stone's trumpet player Cynthia Robinson yelled out in the hit "Dance to the Music": "All the squares go home!"
In modern usage it can be used to describe a person who leads a lawful existence, particularly in regard to employment.
One of the earliest records with the usage of the term can be found in the 1946 recording by Harry Gibson "What's his Story?," which includes the stanza:
Or an earlier song by the same artist, from 1944, called "Stop That Dancing Up There," which includes:
The term was used in the American Cub Scout Promise until 1971.
The chorus of the George M. Cohan song "Mary's a Grand Old Name" concludes with these lines: