Green’s Dictionary of Slang

1. (also jacker-off) a general insult, lit. a masturbator (e,g, at a burlesque show, see cite 1975).

1938		‘Justinian’ Americana Sexualis 26: Jagoff (Jackoff) A man who is presumed to masturbate excessively. Any male disliked because of his idiosyncrasies or unconventional social habits.
1941		in G. Legman Limerick (1953) 258: A young jacker-off of Cawnpore / Never felt a desire for more.
1966		F. Elli Riot (1967) 197: What if those jack-offs from the school building decide to turn ’em loose?
1971		T. Thackrey Thief 312: We spend three hours [...] you jack-off – getting the safe open.
1975		J. Roe Same Old Grind 33: Diane’s languid, pensive strip might enthrall some, but to the men in the runway seats it was bad news. ‘Hey, stuck-up! Shake it! Show it! Do something!’ Her exhorters twiddled their pricks to no avail [...] ‘Boo!’ called a jack-off .
1980		W. Kotzwinkle Jack in the Box 84: The druggist would know you were a jack-off.
1990		S. Morgan Homeboy 74: Nothing too out of place about a jackoff in a Donald Duck suit in this theater.
2000		C. Cook Robbers (2001) 16: Fat jackoff died in the saddle.
2003		H. Hill A Good Fella’s Guide To N.Y. 161: An ‘empty suit’ or ‘jack-off’ was the mobster wanna-be, the guy that just hung around us to feel cool. We were; he wasn’t.
2012		M. McBride Frank Sinatra in a Blender [ebook] You parked your car in my driveway, jackoff!

2. (also jack-and-jill-off) an act of masturbation; thus fig., something worthless or pointless.

1952		in Kerouac letter 11 June in Charters Letters: 1940–56 374: Cut the comedy and crap and personalia jackoffs.
1967		L. Bruce Essential Lenny Bruce 257: Also [...] the terms asshole, jack-off, tits and ass.
1977		H. Crews Feast of Snakes 48: ‘Is that what you think, that they’re going to let you stay in here,’ he pointed to the television, ‘watching that jack-off?’.
1985		‘Thommo’ Dict. Aus. Swearing & Sex Sayings 74: JACK OFF — [W]here a male or female masturbates themselves into orgasm.
1993		Snoop Doggy Dogg ‘Ain’t No Fun’ 🎵 Your back now at the jack-off hour.

3. attrib. use of sense 2.

1967–8		C. Bukowski Notes of a Dirty Old Man (1973) 37: I loved like a crazy jackoff dog turned into a pen of heated female bitches.
1988		N. Eastwood Gardener Got Her n.p.: If he just waited for the right time, he could really have an adventure, a jackoff fantasy come true.
1989		Chapple & Talbot Burning Desires 300: The event that has been billed as ‘the World’s First Jack-and-Jill-Off party’ is [...] a gay masturbation party.
1993		Snoop Doggy Dogg ‘Ain’t No Fun’ 🎵 Your back now at the jack-off hour.
2001		(con. 1964–8) J. Ellroy Cold Six Thousand 182: Holly made the jack-off sign.
2003		J. Ellroy ‘Stephanie’ in Destination: Morgue! (2004) 57: They torqued [...] glue sniffers, hopheads, and public jackoff freaks.

4. as a derog. term of address.

1996		S. Frank Get Shorty [film script] I hope you drive better than you fucking spell, jackoff. My name’s Barboni, not Bar-bone.
1997		C. Hiaasen Lucky You 79: I got a hint for you, too, jackoff: Gimme my money.

5. in fig. use, a hoax, a confidence trick.

1968

T. Wolfe Electric Kool-Aid Acid Test (1969) 391: It’s great to be a part of the greatest jackoff in history.