In thread 21644, containing Jules Allen songs, I have added his version of "Good Bye, Old Paint," from his "Cowboy Lore."
Jules Allen

To thread 14070, Help, Houlihan, Old Paint, have been added restatements of the definitions of hooley-ann, houlihan, and hooligan.
Hoolihan Old Paint

Sorcha, if your dad called throwing a loop to catch a horse a "houlihan, perhaps he was just trying to protect you from the true meaning of the word.
Seriously, however, Rapaire (and you) have a point. Much literature deals with the cattle drives from Texas to the railhead, or to Montana and the Canadian border. This was a short-lived phenomenon, apart from the normal ranching practice that grew up in the 1880s and later. Locally, there were considerable diferences in cowboy culture from region to region. Words were misunderstood and mis-used. Cowhands had a common occupation but different subcultures.

Walt Coburn, in his book "Pioneer Cattleman of Montana," about Robert Coburn who came to Montana in the 1870s and had a large ranch in the 1880s, speaks of some of these differences. He says some big Texas outfits trailed herds into Montana and established additional ranches there, including the XIT, 777, IXL and Turkey Track.
The Texans were born and raised in the cattle industry while many of the ranchers and cowhands in Montana had learned the trade by doing. "Some of the cowhands who came up the long trail ...were tough gun hands... They were a different breed of cowhand for the most part, and most of them spoke border Mexican like natives."
They wore a higher-crowned wider-brimmed hat..."with no dents except a crease down the middle...some tucked their pants legs into their boots...wore large-shanked spurs with rowels that chimed like tinkling bells...rode a double-rigged saddle...shorter ropes...shotgun pull-on chaps or batwing chaps...horses in the remuda were a smaller breed.
"Montana cowpunchers rode a larger-boned, longer-legged horse, stout enough to buck winter showdrifts...Morgan or cross between a Percheron stallion and a Hambletonian mare, or the Nez Perce Appaloosa type."
Conditions were quite different in the Arizona-western New Mexico area, and diffeent customs prevailed from either the Texas or Montana practices.

In none of the books I have about the old ranching days have I found terms like houlihan or Hooley-ann being used. The boys went down to the "hole" (the saloon area). A big whing-ding was called a "jamboree" in Coburn's book. In roping, cowhands threw a loop. That's why I suggest that the terms were late, perhaps originating with the Wild West shows (there were many) and the fledgeling rodeos (The Cheyenne get-to-gether started in 1897).

Sorcha, I wonder if the average working cowboy of some 50 years ago or more, such as your dad, were given a copy of Adams' "Western Words," how many terms would he find that he had never heard or had heard with another meaning.   
A great grandfather of mine was driving cattle for the Commissary in the Civil War period and eventually owned ranches later sold to the Maxwell Grant in New Mexico. Another ranched and mined in southern Colorado from 1877 on. In stories told by a grandfather, few of these terms appeared, and when they did, they were Spanish.