Green’s Dictionary of Slang

cough n.

[cough v.]

1. a payment, the handing over of money.

[US]T.J. Hains Mr Trunnell Mate of the Ship ‘Pirate’ Ch. i: They wanted me to cough up stuff for the whole crowd. But nary a cough. One or two drinks is about all I can stand.

2. a confession (esp. one that is presumed to be sincere and factual); also attrib.

[UK]J. McClure Spike Island (1981) 98: He’s going to say he was tricked into this cough statement.
[UK]H.R.F. Keating Soft Detective 204: Putting the fear of God in them’s the way to get a cough.

In compounds

cough syrup (n.)

1. (US Und.) bribe money.

[US] (ref. to c.1925) Wentworth & Flexner DAS 125/1: cough syrup Bribe money paid to keep another from informing or coughing up information.

2. see cough medicine

SE in slang uses

In compounds

cough drop (n.)

1. (Aus./S.Afr.) a pretty woman.

[Aus]Dead Bird (Sydney) 27 Sept. 5/3: If you should want a tart, Ask a Special. / He knows their names by heart, / Does a Special. / He can fit you in a trice / With a cough-drop plump and nice.
[UK]Partridge DSUE (8th edn) 258/1: S. Africa 1942+.

2. a disagreeable person; the image is of an informer [cough v. (1)].

[UK]Referee 27 July in Ware (1909) 94/2: ‘Honest John Burns,’ who has been returned for Battersea by the skin of his teeth, and who would have benefited considerably had his constituents given him a holiday, objects to being called ‘a cough drop’.
[UK]W.W. Jacobs ‘Artful Cards’ in Monkey’s Paw (1962) 314: Fair old cough-drop, ain’t he?

3. a challenge, i.e. that which is ‘hard to swallow’.

[UK]Mirror of Life 3 Aug. 14/1: Lynch is a good two-handed fighter and clever, and will be a severe cough drop for most lads at his weight.

4. a ‘character’, a ‘card’.

[UK]T.W.H. Crosland ‘The Bold Militiaman’ in Absent-Minded Mule and Verses 14: Fine fellows for parade, / Done up in tasty tunics / An’ sashes an’ gold braid, / An’ loved by all the slaveys, / An’ cough-drops at their trade.
[UK]W.L. George Making of an Englishman III 317: ‘You are a cough-drop,’ she said. ‘Why, you must be barmy chucking up a good job like that.’.
[UK]J.B. Priestley Good Companions 269: Yond’s a coughdrop.
[UK]J. Curtis They Drive by Night 166: You are a funny boy. Regular cough drop, that’s what I call you.
[UK]J. Franklyn Cockney 286: ‘A lad’ in cockney slang means simply a witty, impertinent, or daring, person of either sex. [...] It is synonymous with a one, a card, a caution, a cough-drop, and very largely with an ’erb.

5. poison, or anything disagreeable [the slogan of a popular cough lozenge, ‘cough no more’].

[UK]Marvel XV:373 Jan. 13: Give the beauties leaden cough-drops!
[UK]J. Ware Passing Eng. of the Victorian Era.
cough medicine (n.) (also cough syrup)

(US) whisky.

Marshall Co. Republican (Plymouth, IN) 21 Feb. 3/1: We observe that whisky labeled ‘cough medicine’ is the favorite beverage of some heavy literary men.
[US]Salt Lake Trib. (UT) 13 Feb. 3/6: ‘Give me twelve bottles of cough medicine.’ [...] He inquired if there was sickness in the family. ‘Why, no,’ replied the purchaser. ‘Are you not wise? This is only booze’.
Small Story of 47tb 128: Everybody invests in a little ‘cough medicine.’ [Ibid.] 128: No more ‘cough syrup.’ [HDAS].
Public ledger (Maysville, KY) 30 Nov. 4/1: Prohibition agents [...] confiscated $600 worth of gin and ‘cough medicine’.

In phrases

soften one’s cough (v.)

(Irish und.) to render someone susceptible to confessing.

[Ire]Breen & Conlon Hitmen 119: A year in custody had not softened Wilson’s cough.