Green’s Dictionary of Slang

1. to improvise, to ad lib, to play a situation by ear without practice or rehearsal; thus winging n.

1895		Crowe Aus. Sl. Dict. 96: Wing it, a theatre phrase for actors who are prompted on their parts from the wings.
1899		W.J. Kountz Billy Baxter’s Letters 22: Let any of these fellows who own horses get a soak on, and they get to be a kind of a village pest, with their talk about blowing up in the stretch [...] etc. Now, since when did a horse get an arm? They have got me winging. I can’t follow them at all.
1905		A. Binstead Mop Fair 210: Seeing no harm in winging a little, he replies, with absolute truth.
1916		J. Lait ‘Canada Kid’ in Beef, Iron and Wine (1917) 181: It’s got me wingin’, too. I keep right on workin’ — I lift a boob for $106.60 on a mainstem caboose yesterday.
1924		H.L. Wilson Professor How Could You! 230: You don’t quite put that over – you ain’t up to the lines yet; you’re still winging the part.
1941		Lena Horne ‘Aunt Hagar’s Blues’ 🎵 Said he, ‘No wingin’, no ragtime singin’ tonight.’.
1969		C. Brown Mr Jive-Ass Nigger 191: How could she possibly know about the jiveass nigger? [...] Could she ever know he was winging it?
1979		E. Torres After Hours 57: They can’t wing it any more. Gotta do the paperwork.
1989		M. Amis London Fields 117: I guess I could just wing it. But all I know for sure is the very last scene.
1995		C. Hiaasen Stormy Weather 243: She was winging it with the lyrics.
2006		C. Hiaasen Nature Girl 67: She was obviously winging it, so Fry dropped the subject.
2013		K. Sampson Killing Pool 59: He hates having to accept that there are some things he just has to wing.
2016		T. Robinson Rough Trade [ebook] I was winging it.
2021		J. Ellroy Widespread Panic 107: He’d wing it, wham-bam.

2. in attrib. use of sense 1.

2010

Codella and Bennett Alphaville (2011) 112: Those winging-it, what-the-hell situations.

3. to move fast, to ‘fly’.

1909		H. Green Mr. Jackson : I ain’t had no sleep in three days, but I ain’t wingin’ yet, pal. I kin keep it up.
1917		Van Loan ‘The Last Chance’ in Old Man Curry 109: Still up in front and winging, just winging.
1945		W.R. Burnett Tomorrow’s Another Day 183: [A]fter the first few jumps she [a racehorse] was ahead of the field and on the rail, winging.
1960		Mad mag. June 46: Some cruising stud come winging.
1960		Baltimore Sun (MD) Sun. Mag. 4 Dec. 9/2: Blowing the pad means leaving, going home, flaking off, winging it, squealing out.
1970		Gaddis & Long Panzram (2002) 25: The more daring passenger learned to wing aboard passenger trains between the coal tender [...] and the baggage car.
1978		T. O’Brien Going After Cacciato (1980) 237: ‘Another two hours [...] Maybe less if you wing it.’ So Paul Berlin winged it. Flat-out through the Anatolian flatlands.

(UK black) to leave, to go away.

1997

C. Newland Scholar 137: All right people, I’m wingin’ out anyway.