Green’s Dictionary of Slang

1. (orig. US) a failure, esp. a socially inadequate person.

1902		Ade Girl Proposition 91: Just when Tess figured herself a sure Loser, some one hit her in the Back and called her Sis.
1919		Marvel 1 Mar. 5: You’re a loser, Pye. There’s nothing on the chap to hash, but he’ll make soup.
1927		H.C. Witwer Classics in Sl. 16: Gremio and Hortensio, the two losers, is standin’ on the corner tryin’ to kid each other that the world is full of Blanches and what’s one more or less.
1946		G. Gibson Enemy Coast Ahead (1955) 203: He is backing a real loser.
1955		B. Schulberg On the Waterfront (1964) 156: It made him smile to think of this bunch of losers making trouble for [...] Johnny Friendly.
1962		R. Cook Crust on its Uppers 16: Maybe, too, glamour always surrounds a loser.
1965		Wisconsin State Jrnl 17 Jan. 1-2: On the other side would be the girl or guy called a ‘loser’ or a plain-looking date with no personality.
1973		Sun. Times Mag. 7 Oct. 96: Emigration is for losers, I’m afraid.
1989		T. Blacker Fixx 15: I’d be obliged to describe Father as something of a loser.
1990		S. Morgan Homeboy 59: I work too hard for my money to put it on losers and lunatics.
1996		P. Howard The Joy (2015) [ebook] [H]e’d tell them all about the junkie loser he had in the car earlier.
2000		P. Howard Miseducation of Ross O’Carroll-Kelly (2004) 61: ‘Why don’t you ask lover-boy?’ [...] ‘He’s a loser, Ross.’.
2004		L. Redhead Peepshow [ebook] It was Monday morning and people were off to work. Losers.
2005		Mad mag. June 33: This is awesome! [...] Everyone here is a bigger loser than me.
2010		J. Ellroy Hilliker Curse 6: The Main Loser and the Main Blonde got in a fender bender.
2012		J. Fagan Panopticon (2013) 44: He crosses the road and smirks back at me. Loser. Fucking troll.
2018		I. Welsh Dead Man’s Trousers 113: The socially awkward, ginger-heided loser.
2019		N. Walker Cherry 291: He was pissed off because he was a fucking loser.
2021		T. Pluck Boy from County Hell 123: [T]he usual cliche skulls, nooses, knives, and iron crosses found on Nazi losers.

2. (US) a convicted prisoner, one who served a jail sentence; often ext. by a number that denotes the number of sentences; thus two-time loser n.; three-time loser under three adj.

1908		implied in three-time loser under three adj.
1912		D. Lowrie My Life in Prison 54: Here I am a five-time loser.
1914		Jackson & Hellyer Vocab. Criminal Sl. 56: loser [...] current amongst prison habitues. An ex-convict.
1921		P. & T. Casey Gay-cat 166: A loser, a convict, had jes’ escaped from Joliet.
1928		Flynn’s Weekly 4 Feb. 436/1: Big Bill Douglas was enjoying a year’s vacation from his usual haunts up at Sing Sing at the expense of the State. To his underworld associates he was doing a short bit in the Big House, or a one time loser.
1950		Goldin et al. DAUL 129/1: Loser. (P) Anyone convicted of a felony. [A second felony conviction makes one a ‘two-time loser’; a third conviction, a ‘three-time loser,’ etc.].
1958		F. Norman Bang To Rights 7: After all, a five-time loser – as we Americans phrase it – is badly handicapped.
1963		B. Hecht Gaily, Gaily 55: Most of the losers who stood briefly on the gallows had been landed there by ‘Ropes’ O’Brien.
1967		M. Braly On the Yard (2002) 4: He had been jailing for thirty of his forty-five years and was now a five-time loser.
1972		E. Grogan Ringolevio 107: A four-time-loser dope fiend.
1973		E. Bunker No Beast So Fierce 10: He used wit [...] to diminish confrontation with his own failures (he was a four-time loser).
1994		T. Willocks Green River Rising 218: He wouldn’t let one of our guys twist a fucken ankle to save that bunch of losers.
2002		J. Lerner You Got Nothing Coming 30: Before I give you losers your cell assignments, you’re all going to shower.

3. (orig. US) a disappointment, a problem, an obstacle, a useless thing or idea.

1927		R.S. Gold ‘Miscellaneous Notes’ in AS III:2 167: Set Up: Certain loser.
1936		J. Curtis Gilt Kid 287: It was a bit of a loser, feeling bored before the trial had started.
1937		J. Curtis You’re in the Racket, Too 251: He’d have to get straight out of the West End, straight out of the smoke most likely. And that was a bit of a loser when he had a pocketful of dough.
1977		E. Torres Q&A 54: This junkie will show up in night court with a turban around his head and say I assaulted him, his wife, and his baby en route to the hospital [...] This is a loser, fuck it.
1981		J. Wambaugh Glitter Dome (1982) 251: He’s riding a string of losers. I believe he’s on his way out.
1995		J. Cameron Vinnie Got Blown Away 64: I was there and Wayne Sapsford got to be a loser and Vinnie.
2000		Indep. Rev. 5 Jan. 4: But Newport – an absolute food desert – is a clear loser.