Green’s Dictionary of Slang

1. (also flopperoo) a failure, esp. of a film or stage play; also attrib.

1890–1904		Farmer & Henley Sl. and Its Analogues.
1920		R. Lardner Big Town 217: I got a flop on my hands unlest I can get a couple of ideas.
1928		W. Winchell Your Broadway & Mine 5 Dec. [synd. col.] Another flop show [...] is being doctored by ‘humor’ specialists.
1929		F. Borden ‘Guns of Gangland’ in Gangster Stories Dec. 🌐 Not that his act is any good—the kid is a worse flop each night.
1934		J.M. Cain Postman Always Rings Twice (1985) 61: It was the worst flop of a home-coming you ever saw in your life.
1942		W. Winchell On Broadway 27 May [synd. col.] ‘Popularity,’ Cohan’s first and only flopperoo, was recognised by everyone [...] as a turkey.
1947		A. Baer in Waterloo (IA) Daily Courier 19 Jan. 35/1: A refill in a Brooklyn movier theater who went in to take the place of a flop orchestra.
1947		B. Schulberg Harder They Fall (1971) 242: Why are you [...] afraid to try anything better than you’re doing — for fear you’ll be a flop?
1951		Cusack & James Come in Spinner (1960) 19: That Mystery of the Orient line had been a bit of a flop since the Jap war had taken the lid off Eastern glamour.
1963		G. Lambert Inside Daisy Clover (1966) 161: His play was a terrible flop, thumbs down from every newspaper in town.
1976		Cab Calloway Of Minnie the Moocher and Me 73: We were an absolute flop.
1989		M. Amis London Fields 250: The bottle of porno passed through the dust to settle the crime buzz and the crime flop.
1992		D. Jarman diary 1 Aug. Smiling in Slow Motion (2000) 182: One box office flop and your company is bankrupt.
2004		J.J. Fox How to Make Big Money in Your Own Small Business 63: The product was launched at $1.99 and was a complete flop.
2012		D. Spivey ‘If You Were Only White’ 85: The setting was perfect for a hero or an absolute flop.

2. a fat, ungainly, slovenly person, esp. a woman.

1909		H.G. Wells Tono-Bungay II 171: All the little, soft feminine hands, the nervous ugly males, the hands of the flops, and the hands of the snatchers!
1923		Glasgow Herald 12 Dec. 10: If that little flop [...] believes he can play fast and loose with the moral consciousness of this nation .
1936		F. O’Connor Bones of Contention 70: She was a great flop of a woman [OED].

3. (US Und.) an arrest.

1904		Number 1500 Life In Sing Sing 248: Flop. An arrest.
1916		J. Lait ‘Canada Kid’ in Beef, Iron and Wine (1917) 153: I was pretty near thirteen before I takes my firs’ flop.
1924		G. Henderson Keys to Crookdom 404: To take a flop – to get arrested.
1949		Monteleone Criminal Sl. (rev. edn).
1950		Goldin et al. DAUL 72/1: Flop [...] An arrest. ‘Tony the Junker took a flop on a dead-banger (red-handed).’.

4. a dull, unpleasant person, a misfit, a failure.

1923		H.C. Witwer Fighting Blood 237: I couldn’t of been such a flop or they’d never take a chance like that on nothing but my word.
1935		(con. 1920s) J.T. Farrell Judgement Day in Studs Lonigan (1936) 586: If he hadn’t been such a damn tongue-tied flop with shaking knees.
1941		V. Davis Phenomena in Crime 226: The old lags are the flops and ‘has-beens’ of the rackets.
1952		Lait & Mortimer USA Confidential 50: He was a miserable flop.
1969		P. Theroux Murder in Mount Holly (1999) 19: Two voices – one from the radio, one from the seat next to him – sassed him, told him he was a useless old fool, a flop.
1984		‘Derek Raymond’ He Died with His Eyes Open 105: It [i.e. a school] turned out flops, would-be revolutionaries, drug addicts and trendies by the score.
2000		P. Temple Dead Point (2008) [ebook] Barry Moran, a seminary flop who had joined the legion of other faith-challenged but inordinately sensitive people.

5. (US prison) the rejection of one’s application for parole.

1935		A.J. Pollock Und. Speaks 41/1: Flop, parole board not acting on application (prison).
1949		Monteleone Criminal Sl. (rev. edn).
1972		(con. 1950s) D. Goines Whoreson 183: The parole board had given flop, but that didn’t make any difference.
1983		R. Klein Jailhouse Jargon and Street Sl. [unpub. ms.].

6. (UK Und.) anywhere used for the division of criminal spoils.

2007

N. ‘Razor’ Smith Raiders 172: At the flop, when they counted the take, it came to just over £7,000. [Ibid.] 205: £3000 in loose change that nobody even wanted to pick off the carpet of the flop.