Green’s Dictionary of Slang

1. to play truant from school.

1848		Bartlett Dict. Americanisms.
1859		T.F. Upson diary Mar. in Winther With Sherman to the Sea (1958) 4: H.M. and I played hookey one day and went down in the woods. When we got back to school the teacher wanted to know where we had been.
1871		Brooklyn Dly Eagle (NY) 9 Feb. 2/5: Children ‘Take the Chances’ by playing ‘hookey,’ or by real hooking.
1876		‘Mark Twain’ Tom Sawyer 19: He’ll play hookey this evening, and I’ll just be obleeged to make him work, to-morrow, to punish him.
1887		G. Devol Forty Years a Gambler 9: When my parents thought me at school, I was playing ‘hookey’ with other boys, running about the river [...] and having a fight nearly every day.
1891		J.A. Riis How the Other Half Lives 104: Nor is there any suspicion that the rest are playing hookey. They stay honestly home to celebrate.
1894		Shiner Gaz. (TX) 20 Dec. 2/5: How I wisht I had gone 2 scool and not plade hooky.
1904		B.L. Farjeon Amblers 295: ‘Playing hookey?’ suggested Colley.
1907		Frankfort Roundabout (KY) 2 Mar. 1/2: To go to school or not to go to school, that’s the question. / To play hookie and have a good time, / To play hookie and perchance get caught [etc.].
1909		J.W. Carr in ‘Word-List From Northwest Arkansas’ in DN III:v 398: hooky, to play, v. phr. To stay away from school. ‘Johnnie played hooky this morning.’.
1914		S. Lewis Our Mr Wrenn (1936) 42: I’m as scared as teacher’s pet playing hookey for the first time.
1922		NY Tribune 29 Jan. 65/2: [pic. caption] Lloyd George [...] playing hooky [...] in a little golf.
1923		Wodehouse Inimitable Jeeves 150: He’s played hookey from the choir so often.
1926		J. Black You Can’t Win (2000) 23: I also learned to play ball, football, marbles, and, I must admit, hooky, the most fascinating of all small-boy games.
1932		(con. 1919) Dos Passos Nineteen Nineteen in USA (1966) 584: Let’s play hookey and have a swell time.
1935		Cleo Brown ‘Lookie, Lookie, Here comes Cookie’ 🎵 Just a little angel, playing hooky, / From heaven on high, oh my, / Sweet as pumpkin pie.
1939		Wodehouse Uncle Fred in the Springtime 80: ‘The Boss being away, I am playing hookey at the moment’.
1943		C. McCullers Heart is a Lonely Hunter (1986) 303: Two or three days she played hooky from school.
1945		R.M. Lindner Stone Walls and Men 204: That day I played ‘hookey’.
1953		J. Thompson Criminal (1993) 35: You make a fool out of me with your hooky-playing.
1959		W. Brown Teen-Age Mafia 93: Boosting from the dime store. playing hooky.
1968		T. Wolfe Electric Kool-Aid Acid Test (1969) 215: It seemed that some kid had been playing hooky from school in New York that day.
1976		Cab Calloway Of Minnie the Moocher and Me 7: I played hooky, hung about in the streets.
1984		Grandmaster Melle Mel ‘Hustler’s Convention’ 🎵 I learned to be cool while playin’ hooky from school.
1993		S. King Dolores Claiborne 302: Not even the hellions will play on em after school lets out, or on the days when they play hookey.
2000		P. Beatty Tuff 60: Playing hooky in the Village one day. Walked past a marquee on this little place that said 400 Blows.
2010		A. Steinberg Running the Books 116: The inmate students could run but they couldn’t hide. It was impossible to play hookie in the joint.
2012		D. O’Donnell Locked Ward (2013) 230: Playing hookey. Plugging it, as they said when I was at school.
2018		T. Pluck ‘Hot Rod Heart’ in Life During Wartime 117: He played hooky the next day and drank with them.

2. in fig. use, to be absent, missing.

1906		C. M’Govern Sarjint Larry an’ Frinds 28: A shrivelled up carcase dat showed dat for the year at least she must have been playing hookey from a cemetery.
1912		G.R. Chester Five Thousand an Hour Ch. vi: I think I’ll play hooky. I don’t want to break up the party.
1936		Archie Seale Man About Harlem 18 Apr. [synd. col.] Dick Seay [...] is still playing hookey in Harlem.
1972		E. Grogan Ringolevio 277: Youngsters who were playing hooky from suburbia.
1979		‘Iceberg Slim’ Airtight Willie and Me 32: His watch and stickpin were playing hooky.

3. to be adulterous, to cheat on a partner.

1930		E.H. Lavine Third Degree (1931) 156: The safest racket in the world is to rob a married man or woman who is playing hookey.
1941		Willie ‘61’ Blackwell ‘Four O’clock Flower Blues’ 🎵 I’m not jealous but I’m superstitious, the most working men is that way; If I catch you playing hookey, ooh Lord, Lord, Betty June, what a day, what a day.