Green’s Dictionary of Slang

loser n.

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

[US]Ade Girl Proposition 91: Just when Tess figured herself a sure Loser, some one hit her in the Back and called her Sis.
[UK]Marvel 1 Mar. 5: You’re a loser, Pye. There’s nothing on the chap to hash, but he’ll make soup.
[US]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.
[UK]G. Gibson Enemy Coast Ahead (1955) 203: He is backing a real loser.
[US]B. Schulberg On the Waterfront (1964) 156: It made him smile to think of this bunch of losers making trouble for [...] Johnny Friendly.
[UK]R. Cook Crust on its Uppers 16: Maybe, too, glamour always surrounds a loser.
[US]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.
[UK]Sun. Times Mag. 7 Oct. 96: Emigration is for losers, I’m afraid.
[UK]T. Blacker Fixx 15: I’d be obliged to describe Father as something of a loser.
[US]S. Morgan Homeboy 59: I work too hard for my money to put it on losers and lunatics.
[Ire]P. Howard The Joy (2015) [ebook] [H]e’d tell them all about the junkie loser he had in the car earlier.
[Ire]P. Howard Miseducation of Ross O’Carroll-Kelly (2004) 61: ‘Why don’t you ask lover-boy?’ [...] ‘He’s a loser, Ross.’.
[Aus]L. Redhead Peepshow [ebook] It was Monday morning and people were off to work. Losers.
[US]Mad mag. June 33: This is awesome! [...] Everyone here is a bigger loser than me.
[US]J. Ellroy Hilliker Curse 6: The Main Loser and the Main Blonde got in a fender bender.
[UK]J. Fagan Panopticon (2013) 44: He crosses the road and smirks back at me. Loser. Fucking troll.
[Scot]I. Welsh Dead Man’s Trousers 113: The socially awkward, ginger-heided loser.
[US]N. Walker Cherry 291: He was pissed off because he was a fucking loser.
[US]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.

implied in three-time loser under three adj.
[US]D. Lowrie My Life in Prison 54: Here I am a five-time loser.
[US]Jackson & Hellyer Vocab. Criminal Sl. 56: loser [...] current amongst prison habitues. An ex-convict.
[US]P. & T. Casey Gay-cat 166: A loser, a convict, had jes’ escaped from Joliet.
[US]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.
[US]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.].
[UK]F. Norman Bang To Rights 7: After all, a five-time loser – as we Americans phrase it – is badly handicapped.
[US]B. Hecht Gaily, Gaily 55: Most of the losers who stood briefly on the gallows had been landed there by ‘Ropes’ O’Brien.
[US]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.
[US]E. Grogan Ringolevio 107: A four-time-loser dope fiend.
[US]E. Bunker No Beast So Fierce 10: He used wit [...] to diminish confrontation with his own failures (he was a four-time loser).
[US]T. Willocks Green River Rising 218: He wouldn’t let one of our guys twist a fucken ankle to save that bunch of losers.
[US]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.

[US]R.S. Gold ‘Miscellaneous Notes’ in AS III:2 167: Set Up: Certain loser.
[UK]J. Curtis Gilt Kid 287: It was a bit of a loser, feeling bored before the trial had started.
[UK]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.
[US]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.
[US]J. Wambaugh Glitter Dome (1982) 251: He’s riding a string of losers. I believe he’s on his way out.
[UK]J. Cameron Vinnie Got Blown Away 64: I was there and Wayne Sapsford got to be a loser and Vinnie.
[UK]Indep. Rev. 5 Jan. 4: But Newport – an absolute food desert – is a clear loser.

In derivatives