Green’s Dictionary of Slang

flyer n.2

also flier

1. a game, a ‘lark’.

[UK]‘Answer to Captain Morris’ in Hilaria 77: Such pieces we push at, of pure flesh and blood; / Take a flyer in town, ’tis a hot butter’d bun, / And you’re certain to pay thro’ your nose for your fun.
[Ire]‘A Real Paddy’ Real Life in Ireland 280: From whim and frolic...he would go into the racket court in the Marshalsea, and have a flyer with any prisoner for a few pots of porter, hit or miss.
[US]‘Mark Twain’ Innocents Abroad 357: In the Hellespont we saw where Leander and Lord Byron swam across [...] merely for a flyer, as Jack says.
[US] in ‘Mark Twain’ Sketches New and Old 312: It so happened that we stepped into the Revere House, thinking maybe we would chance the salt-house in that big dining-room for a flyer, as the boys say.

2. a wager or investment.

[US]R. Waln Hermit in America on Visit to Phila. 2nd series 29: Let’s have a flyer if you’re flush.
[US]Spirit of the Times (N.Y.) 11 July 229/3: Lend me a quarter [...] just for a flyer.
[US]Matsell Vocabulum.
[US]J. O’Connor Wanderings of a Vagabond 447: ‘I’ll go yer a hundred fur a flyer,’ now sung out another capper, who up to this moment had remained a silent spectator of the scene.
[UK]Pall Mall Gazette 26 Aug. 11/1: He [...] turned to the Wall-street news to see how much he had already made on his flyer .
[US]Wichita Eagle (KS) 11 Nov. 7/1: If a man every goes back to the table to play a little flyer after having made a large winning he’s a ‘goner’.
[US]S. Ford Shorty McCabe 35: He goes off and leaves his good money up, just on a flier like that.
[US]Ade Hand-made Fables 294: The Matrimonial Speculation—that’s more than a Flier. Margins don’t go. The Geek has to set in his whole Stack.
[US]O.O. McIntyre New York Day by Day 31 Aug. [synd. col.] Men who have their ‘flyers’ in Wall street go to him for consolation.
[US](con. 1920s) Dos Passos Big Money in USA (1966) 908: Suppose you try a little flyer in Auburn just to get your hand in.
[US]Goldin et al. DAUL 71/2: Flier. Any risky, unplanned act; a desperate gamble; going to trial against overwhelming odds.

3. a try; an attempt.

[US]‘Mark Twain’ Sketches New and Old (1926) 170: My refusal of the position at $7,000 a year was not precisely meant to be final, but was intended for what the ungodly term a ‘flyer’—the object being to bring about an increase in the amount.
[US]‘Mark Twain’ Connecticut Yankee 113: The boys all took a flier at the Holy Grail now and then. [Ibid.] 424: I chanced another flyer.
[US]H.C. Witwer Fighting Blood 123: It wasn’t long before I took a flyer at this game again.
[US]A.J. Liebling Honest Rainmaker (1991) 100: Ricecakes, during his short flyer with the Spirit of the Times, had gained insight into how much money could be made [etc.].

In phrases

take a flier (v.) (also take a flyer) [SE take a flying leap]

1. to have quick and spontaneous sexual intercourse with both parties fully or partially dressed.

[UK]Grose Classical Dict. of the Vulgar Tongue n.p.: To take a flyer, to enjoy a woman with her clothes on, or without going into bed.
[UK]Lex. Balatronicum [as cit. 1785].
[UK]Egan Grose’s Classical Dict. of the Vulgar Tongue.
[UK]Farmer Vocabula Amatoria (1966) 31: Faire une barbe. To copulate; ‘to take a flyer’.

2. to go out on a spree.

[US]I.L. Allen City in Sl. (1995) 65: To go on a tear, to take a flyer, or especially to make whoopee was the way nightlifers spoke of these tamer sprees in the 1920s.

3. (US) to take a chance, to gamble, esp. financially.

[US]W.W. Fowler Ten Years in Wall Street 37: As for those who take ‘flyers’ in one or two hundred shares, they are a great host whom no man can describe, much less enumerate.
[US]H. Blossom Checkers 8: I ’m jes’ takin’ a flyer on her to win today.
[US]H. Green Actors’ Boarding House (1906) 158: The hotel’s staff read ‘the dope’ daily and took a flyer, one and all.
[US]‘O. Henry’ ‘Man About Town’ Four Million (1915) 84: The oldest girls are eagerly perusing the financial reports, for a certain young man remarked [...] that he had taken a flyer in Q., X. & Z.
[US]T.A. Dorgan Daffydils 23 Nov. [synd. cartoon strip] If a woman took a flyer in Wall Street would the street cleaner?
[US]H.C. Witwer Fighting Blood 264: Me and Nate and Kayo Kelly has already took a flyer in something apart from the ring.
[US](con. 1920s) J.T. Farrell Judgement Day in Studs Lonigan (1936) 521: He had taken this flyer on Imbray Stock [...] as if it were nothing more than risking a few shekels in a crap game.
[US](con. 1920s) Dos Passos Big Money in USA (1966) 747: He [...] took a flyer for the bit money in connection with a pulpmill started in Maine.
[US]Goldin et al. DAUL 218/1: Take a flier. 1. To commit a crime of gain impulsively, with no foreknowledge or plan. 2. To act impulsively or without plan.
[US] in T.I. Rubin Sweet Daddy 106: Sometimes I take a flyer but mostly I play it both feet on the ground.
[US]J. Thompson Texas by the Tail (1994) 151: Financing? We’ll take a flier on almost anything.
[US]L. Kramer Faggots 20: [It belonged to] Piping Rock sportsmen taking a flyer.
[US]G. Liddy Will (con. 1973) 328: [A] college professor, who had taken a flyer on a marijuana venture, was released on bond .
[US]J. Lansdale Bad Chili 203: They [...] decided you guys had a connection, took a flyer and toted Hap out to the woods.
[UK]K. Sampson Outlaws (ms.) 145: I [...] half thought maybe I could’ve just took a flier and that, could’ve just done a runner and hoped for the best.
[US]J. Stahl I, Fatty 258: He figured what the heck. He’s take a flyer.

4. (US prison) to escape from prison.

[US]Bentley & Corbett Prison Sl. 109: Takin’ a Flier A seldom used expression meaning to escape from prison.

5. to escape, to run away from.

[US]M. Spillane Long Wait (1954) 115: She took a flyer on Lenny and so what.