The term owl-hoot was coined after cock-crow, meaning dawn, to denote dusk. It is first recorded in Noctes Ambrosianæ—Nᴏ LX, published in Blackwood’s Edinburgh Magazine (Edinburgh, Scotland) of February 1832:

O these printers’ devils! Like urchins on an ice-slide, keeping the pie warm, from cock-crow till owl-hoot do they continue in unintermitting succession to pour from the far-off office down upon Moray Place or Buchanan Lodge, one imp almost on the very shoulders of another—without a minute devil-free—crying “Copy! Copy!” in every variety of intonation possible in gruff or shrill.

In American-English slang, the form owlhoot is used in the language of Wild West fiction to denote a fugitive, an outlaw, especially in owlhoot trail with reference to the life of such a person. For example, the Reading Times (Reading, Pennsylvania) of 26^th July 1934 had the following advertisement for one of “Two New Thrilling Magazines on Sale Today for the First Time”:

‘Mavericks’
Five Against the Law!

They were wanted men, those five hard-riding travelers of the still night trail . . . Mavericks all, they had entered outlawry for five different reasons, drawn irresistibly down the Owlhoot Trail from five different walks of rangeland life. They became one living inseparable unit of grim, uncompromising justice, united as one man by their friendship, their burning championship of the underdog—and the high, white flame of their courage . . . A blood-tingling tale of high adventure and heady romance.

Ask for ‘Maverick’s’—15c

The American author Luke Short (1908-75) used to go on the owlhoot and to take to the owlhoot to mean to enter outlawry in the twenty-first instalment of The Man on the Blue, published in the Daily Clarion-Ledger (Jackson, Mississippi) of 9^th December 1936:

“And Mayo submits to that or goes on the owlhoot?” Nancy asked quietly.
“Unless he wants to take up a homestead and brood. Do you think he will?”
“Stop it!” Hyatt commanded. He turned to Nancy. “Sis, I’ve tried to stick by our agreement—to stay put here on the ranch and not fight. But they won’t mix. Either we let Lobell call out the slope and kill us off, or we run—and take to the owlhoot.”

Luke Short used owlhoot in the sense of outlawry in the thirty-second instalment of the novel, published in the same newspaper on 22^nd December of that year:

“From now on it’s the owlhoot for Mayo—and Lee?”
“Would you rather see them swingin’ from that big Navajo pine over there?”

The sense of owlhoot has been extended to a worthless or contemptible person. In Media’s message to Gore: Don’t bother, published in the Press & Sun-Bulletin (Binghamton, New York) of 9^th August 2000, David Rossie wrote, about the 2000 Democratic National Convention:

Poor Al gore. He’s headed for Los Angeles this week, but he might as well be getting in line at the unemployment office for all the good it will do him.
[…]
We are told that Dubyuh* and that gang of owlhoots of his have run off all the Democrats’ issues and put Dubyuh’s Lazy B brand on them.

* Dubyuh: George W. Bush (born 1946), 43^rd president of the USA (2001-09)