Green’s Dictionary of Slang

wail v.

1. (orig. US black) to abandon one’s inhibitions, to lose oneself in an activity, esp. of musicians during an improvised solo, or of sexual pleasure.

[US]Wild One [film script] Now, if you’re gonna stay cool, you’ve got to wail, you’ve got to put something down, you’ve got to make some jive.
[US]‘Lord Buckley’ Hiparama of the Classics 8: Where upon they all started to wail the ‘Love Bridge on the River Ganges,’ a Wild tune with a Sanpan Beat.
[US]N. Heard Howard Street 97: If she git to lookin’ good to you, Shots [...] Just throw her on the bed and wail.
[US]C. McFadden Serial 72: Spenser was wailing with Grace Slick.
[WI]M. Thelwell Harder They Come 349: Dem a loot, dem a shoot, dem a wail — in Shantytown.
[US]M. Myers et al. Wayne’s World [film script] wayne: I hear they [i.e. a band] can wail. tiny: You heard right.
[US](con. 1986) G. Pelecanos Sweet Forever 5: This brother in the movie, he was just wailing on this punch.
[US]B. Coleman Check the Technique 24: ‘We tried to keep shit sparse and funky, but frequently we'd just start wailing, and we'd just keep going from there to see if anything good came out of it’.
‘Elvis Costello’ Unfaithful Music 619: [Aretha Franklin] [...] was absolutely wailing from the moment she entered.

2. (W.I.) to behave badly, aggressively; thus wail down the place, to dance and sing with utter abandon.

[US] ‘Sl. of Watts’ in Current Sl. III:2 51: Wail, v. To fight.
[US]Current Sl. IV:2 10: Wail, v. To criticize.

3. (orig. US black) to sing, to play a musical instrument.

[US]J.A. Williams Night Song (1962) 68: He can wail when he’s right, but he ain’t consistent any more.
[US]H. Selby Jr Requiem for a Dream (1987) 23: Hey, that’s mah man wailin.
[Aus]R.G. Barrett Godson 273: The Bachelors From Cracow could really wail [...] so full of energy you’d think there were twenty on stage, not seven.
[US]R.C. Cruz Straight Outta Compton 17: Thangs you put up with in Soul City when you’re not stinkypie rich or wailing at the Apollo Theatre.
[US]Eble Campus Sl. Nov. 7: wail – play a musical instrument or sing very well.

4. see whale v.1