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. [Internet] ‘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’ [lyrics] 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.
[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]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.
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.
[UK]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.’.