Green’s Dictionary of Slang

hep-cat n.

also hepped cat, hip cat, hipcat
[hep adj. (1) + cat n.5 ; note Gold, A Jazz Lexicon (1964), 143–4: ‘though frequently represented as jazz slang...jazzmen have never used this term in speech except derisively. Its etymology...is based on a Northern white hearing a Southern negro speak hip with a diphthongized vowel sound’]

1. (also hep bird) an aware, sophisticated person.

[US]S. Lewis Babbitt (1974) 140: Something doing, boys. Listen to what the Hep Bird twitters.
[US]D. Burley N.Y. Amsterdam News 25 Feb. 17: A ‘hip cat’ [...] togged out in a draped coat that pinches in sharply at the waist and then blossoms about the hips and ends with a sassy flair.
[US]Pic (N.Y.) Mar. 8: hep cats. — people in the know. All they need is coca-cola and Prima’s music to get high.
D. Burley N.Y. Amsterdam Star-News 22 May 11: Hip-cats who are booted to the play.
[US]‘Hal Ellson’ Duke 45: You just want to be a hep cat with pretty clothes you don’t earn.
[US]L. Durst Jives of Dr. Hepcat (1989) 2: All to do about a hepcat’s dream fine clothes, easy job, good music, pretty girls, swell clubs and a good car.
[UK]‘Raymond Thorp’ Viper 162: A lot of hep cats wanting to get high in a cheap way.
[US]C. Himes Imabelle 60: The customers were the hepcats who lived by their wits.
[US]C. Himes Rage in Harlem (1969) 61: [as 1957].
[US](con. 1950s) H. Junker ‘The Fifties’ in Eisen Age of Rock 2 (1970) 100: Status was divvied up into geographical dualisms: in, out; with it, from squaresville. Hepcat.
[Aus]P. Doyle (con. late 1950s) Amaze Your Friends (2019) 25: Calling All Hepcats! / Learn to play the ELECTRIC guitar in just 6 easy lessons.
[UK]J. Poller Reach 38: Anthony is wearing [...] white toweling socks. ‘Anthony! You crazy hepcat, you.’.
[UK]Guardian Guide 5–11 Feb. 6: Mr Flanders: Hep-cat, goatee-sporting father of Ned. Abandoned concept of parental authority after becoming a ‘freaky beatnik’.

2. attrib. use of sense 1.

[US] ‘Honky-Tonk Bud’ in D. Wepman et al. Life (1976) 54: Honky-Tonk Bud, the hipcat stud, / Stood digging a game of pool.
E. Shrake letter 7 Jan. in Davis (ed) Permanent Wave 236: Willie [Nelson] has ‘blowed my brain,’ to use the hepcat phrase.
[US]N. Heard House of Slammers 86: [as cit. 1964].
[US]T. Piccirilli Last Kind Words 288: He was cool and handsome, hepcat aristocratic.

3. (US black) a jazz or swing fan.

[US]Cab Calloway New Hepsters Dict. in Calloway (1976) Hep cat – a guy who knows all the answers, understands jive.
[US]A. Lomax Mister Jelly Roll (1952) 231: Mister Jelly Roll never bothered his head with these hep-cats, until his bank account at last convinced him that ‘swing’ might not be so bad as he knew it was.
[UK]Guardian Guide 22–28 Jan. 83: Clicking his fingers to the swingin’ hep cats’ groove.
[US](con. 1962) J. Ellroy Enchanters 387: It drew [...] ‘Negro hepcats,’ ‘jazz cats,’ and ‘anyone with a lively wit’.

4. attrib. use of sense 3.

[US]R. Coover Public Burning (1979) 431: ‘Hey, zorch, man!’ his hepcat fans holler.
[US](con. early 1950s) J. Ellroy L.A. Confidential 225: A hepcat drawl. ‘Man, I want to report a murder. If I’m lyin’, I’m flyin’.’.
[UK]Indep. on Sun. Rev. 25 July 28: Hep cat jive talk and what-have-you.