[4] Research and speculation by both amateur and professional etymologists suggest that "hip" is derived from an earlier form hep, but that is disputed.
Many etymologists believe that the terms hip, hep and hepcat derive from the west African Wolof language word hepicat, which means "one who has his eyes open".
Because opium smokers commonly took the drug lying on their sides or on the hip, the term became a coded reference to the practice and because opium smoking was a practice of socially influential trend-setting individuals, the cachet it enjoyed led to the circulation of the term hip by way of a kind of synecdoche.
[7] Slang dictionaries of past centuries give a term hip or hyp meaning melancholy or bored, shortened from the word hypochondriac.
Norman Mailer, one of the voices of the Hipster-Movement, formulated the content-related interpretation of the terms "hip" and "square" in an essay in 1957 as opposites in attitudes towards life, Hip - Square / wild - practical / romantic - classic / instinct - logic / Negro - white / inductive - programmatic / the relation - the name / spontaneous - orderly / perverse - pious / midnight - noon / nihilistic - authoritarian / associative - sequential / a question - an answer / obeying the form of the curve - living in the cell of the square / self - society / crooks - cops / free will - determinism.