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The term "square", in referring to a person, originally meant someone who was honest, traditional, and loyal. The evolution of American culture transformed the term from a compliment to an insult to an obsolete term. It has been said that nowadays, anyone who uses the term "square" to refer to a person, is one.

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the parlance of jazz, a square was a person who failed to appreciate the medium, hence (more broadly) someone who was out of date or out of touch.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 Thelonius 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 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 mostly utilized by beatniks, hippies, yippies, and other individuals who took part in the movements which emerged to contest the more conservative national, political, religious, philosophical, musical and social trends.

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

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 this line:

And there is something there / That sounds so square / It's a grand old name.

L7 is also a derivate term for square. The square shape is made by putting together an "L" made with the left thumb and index finger and a "7" made with the right thumb and index finger. This is similar to the "whatever" "W" and other communications with the hands, such as gang signifying and American Sign Language.

See also

• Hip (slang)
• The Man
• The Establishment

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