Green’s Dictionary of Slang

pain (in the neck) n.1

also pain in the head, ...side

1. a feeling of irritation; see give someone a pain in the neck

2. an annoying person, a bore, a euph. for pain in the arse n.

[[UK]F. Reynolds How to Grow Rich V ii: So, Mr. Pain-in-the-face, (tolatitat) You and the young alderman here have done it].
[US]Van Vechten Nigger Heaven 214: Carvin’s too good fo’ an achin’ pain lak him.
[US]D. Runyon ‘Tight Shoes’ in Runyon on Broadway (1954) 468: This young fellow [...] is known far and wide as a great pain in the neck.
[US]E. Ferber ‘Grandma Isn’t Playing’ in One Basket (1947) 547: Oh, Ma, you’re a pain in the neck!
[US]R.L. Bellem ‘Latin Blood’ in Speed Detective Aug. 🌐 ‘You know how women are.’ ‘Yeah,’ I said. ‘They’re a pain.’.
[US]‘Hal Ellson’ Tomboy (1952) 107: Aw, sometimes he’s a pain in the neck.
[Aus]‘Nino Culotta’ They’re a Weird Mob (1958) 9: One day my boss said to me, ‘Nino, you are a pain in the head.’.
[UK]Wodehouse Jeeves in the Offing 155: [He was] a constant pain in the neck.
[UK]T. Keyes All Night Stand 123: He’s all right [...] but a terrible drag. A terrible pain.
[US]Cab Calloway Of Minnie the Moocher and Me 166: Dizzy was a pain in the neck.
[UK]P. Theroux Family Arsenal 76: You’re a real pain.
[UK]T. Jones Curse of the Vampire Socks 59: Dorothy Jane / I’m afraid, was a pain / In the neck, in the side, in the head.
[US]Pileggi & Scorsese Goodfellas [film script] 107: Jesus Christ! You can be such a pain.
[Ire]R. Doyle Snapper 174: He was becoming a right pain in the neck.
[Ire]F. Mac Anna Last of the High Kings 85: Erin’s a pain [...] but that Rainbow is like something out of TheExorcist.
[UK]Observer 9 Jan. 13: ‘The sponsor was a pain in the neck,’ said one insider.
[UK]A. Sillitoe Birthday 139: He’s a pain most of the time.

3. an annoying situation, anything considered unpleasant, typically a task one does not wish to perform.

[US]Cab Calloway ‘The Worker’s Train’ 🎵 The eight-fifteen is the worker’s train, / The eight-fifteen, and I’m off again, / The eight-fifteen is an awful pain; / Wish I didn’t have to travel on the eight-fifteen!
[Aus](con. 1936–46) K.S. Prichard Winged Seeds (1984) 360: That’s a pain in the neck for the big boys on Wall Street.
[NZ]I. Hamilton Till Human Voices Wake Us 67: Why don’t they let us out and get rid of two pains in the neck, their’s and our own.
[UK]J. McClure Spike Island (1981) 54: Shoplifting’s a pain.
[NZ]G. Newbold Big Huey 31: Their authoritative bellowing and their patronising advice grew to be a pain in the neck.
[UK]N. Cohn Yes We have No 228: What was acceptable before is now a royal pain.
[Aus] J.J. DeCeglie ‘Death Cannot Be Delegated’ in Crime Factory: Hard Labour [ebook] The [...] backtracking it [i.e. murder] forced one to do just so as to keep your arse out of jail, real pain in the neck it was.

4. (Aus.) a general insult.

[Aus]G. Seal Lingo 127: In between [the extremes of insult lies an enormous and subtly graded range of possibilities that include the following: arseache; arsehole; [...] pain in the neck/arse.

In phrases

give someone a pain in the neck (v.) (also give someone an ache, ...a pain in the ear, ...face, ...guts, ...teat)

of a person, thing or situation, to irritate someone.

[US]C.F. Lummis letter 10 Dec. in Byrkit Letters from the Southwest (1989) 142: That began to give me a pain.
[US]St Paul Globe (MN) 20 Oct. 9/5: You give me a pain.
[US]Star-Gaz. (Elmira, NY) 15 May 4/3: Yale College Slang [...] [H]e [i.e. a tutor] gives me a pain in the neck.
[US]S. Crane George’s Mother (2001) 88: I was on’y sayin’ that this gettin’-up business gives me a pain.
[UK]Sporting Times 12 May 1/4: He may over-exercise it and give his long-suffering customers a dull pain in the neck.
[US]H. Green Actors’ Boarding House (1906) 110: Them mutts gimme a pain!
[US]S. Ford Shorty McCabe 165: For a girl that had a whole bunch of Johnnies on the waitin’ list, and her with only one best dress to her name at the time, you give me an ache.
[US]H. Green ‘At the Actors’ Boarding House’ in Galena Eve. Times (KS) 10 June 4/3: ‘That hotel guy is a rough man.’ [...] ‘His funny rules give me a pain’.
[US]Wash. Post 8 Oct. E3: Aw, you pikers gimme a pain in the neck.
[UK]Hall & Niles One Man’s War (1929) 159: And the visiting Americans [...] They give me a pain.
[UK]D.L. Sayers Unpleasantness at the Bellona Club (1977) 198: Well, it gives me a pain [...] But I thought perhaps that was my lack of artistic education.
[Ire]S. O’Casey Juno and the Paycock Act II: The two o’ them ud give you a pain in your face.
[US]J. Tully Beggars of Life 125: Them damn Johnny Bulls gimme a pain in the ear.
[US](con. 1918) W.T. Scanlon God have Mercy on Us! (1930) 4: What gives me a pain in the neck is all the time we wasted up at Verdun.
[US]V.F. Nelson Prison Days and Nights 25: Don’t that give you a pain in the neck?
[US]‘Boxcar Bertha’ Sister of the Road (1975) 86: These plutocrats with cars give me a pain.
[US]I. Shulman Amboy Dukes 45: You’re a pretty nice guy [...] but you still give me a pain.
[US]J.D. Salinger Catcher in the Rye (1958) 33: That’s something else that gives me a royal pain.
[WI]R. Mais Hills were Joyful Together (1966) 144: You gimme a pain in the guts.
[Aus]D. Niland Gold in the Streets (1966) 139: God, they’d give you a pain in the teat.
[UK]A. Wesker Chips with Everything II ix: Ah, you give me a pain in the neck, you do, you’re a coward.
[UK]Sun. Times 5 June n.p.: ‘How do you know those aren’t just frightened peasants?’ ‘Running? Like that? Don’t give me a pain.’.