Square used as slang may mean many things when referring to a person or in common language. It is often used to speak of a person who is regarded as dull, rigidly conventional, and out of touch with current trends.
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In referring to a person, the word originally meant someone who was honest, traditional and loyal. An agreement that is equitable on all sides is a "square deal". During the rise of jazz music, the term transformed from a compliment to an insult.
Negative connotations
In the parlance of jazz, a square was a person who failed to appreciate the medium, or, more broadly, someone who was out of date or out of touch, hence the saying "be there or be square".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 1940s, beatniks in the 1950s, hippies in the 1960s, yippies in the 1970s, 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 comes from the square representing a four-beat rhythm as shown by a conductor's hands. 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!" If the counterculture was a shift from conservatism to liberalism, then square was what liberal people called conservative people and things. While the term waned in popularity during the 1980s, it remained in the public consciousness, particularly of the American baby boom generation, enough that its broad meaning (of a person who respects traditional principles) is exemplified in Huey Lewis's 1986 hit "Hip To Be Square".
The term found its way into various parts of popular culture. Perhaps the most obvious recurring reference today would be this line from "Jailhouse Rock", a song most famously sung by Elvis Presley:
The warden said hey buddy don't you be no square If you can't find a partner use a wooden chair.An early example of the usage of the term can be found in the 1946 recording by Harry Gibson, who performed as Harry the Hipster, "What's his Story?" which includes the stanza:
At the gate stands a sinning fool Shouting "Lordy Lordy" Saint Peter said "You square, Your place is way down there" And the square said, "What's his story?"In 1945 the song "Tampico" by Stan Kenton contained the lyrics:
"You ask a Mexican band to play a "rumba-down-dare" there, He turns and Says to the boys, "Hey fellas, dig that square!"
Or an earlier song by Harry Gibson, from 1944, called "Stop That Dancing Up There," which includes:
The people downstairs Say I'm an awful square When I shout, "Stop that dancing up there."Positive connotations
Square can mean good and honest, first attested in the 1560s, a sense preserved in the phrases "fair and square", "a square deal"; or upstanding, as in "squaring up" (to an antagonist). As a symbol of rectitude, the square, or set-square, is one of the principal allegorical symbols in Freemasonry.
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:
And there is something there / That sounds so square / It's a grand old name.'Square' is also an obscure Canadian slang term for a case of 24 beer bottles.
'Square' is also a slang term for a cigarette among the African-American community.