In Great Britain heights under 2,000 feet are generally called hills; 'mountain' being confined to the greater elevations of the Lake District, of North Wales, and of the Scottish Highlands; but, in India, ranges of 5,000 and even 10,000 feet are commonly called 'hills,' in contrast with the Himalaya Mountains, many peaks of which rise beyond 20,000 feet. [OED]Phrase over the hill "past one's prime" is first recorded 1950.
The term mountain is very loosely used. It commonly means any unusual elevation. In New England and central New York, elevations of from one to two thousand feet are called hills, but on the plains of Texas, a hill of a few hundred feet is called a mountain. [Ralph S. Tarr, "Elementary Geology," Macmillan, 1903]
Despite the differences in defining mountain systems, Penck (1896), Supan (1911) and Obst (1914) agreed that the distinction between hills, mountains, and mountain systems according to areal extent or height is not a suitable classification. ["Geographic Information Science and Mountain Geomorphology," 2004]
Then again, I do not think It will do so well. I would hate to see some old railroad man come here and take my job, and then, I don t think It is right to hire some Hill Billy and give him the same right as I just because he was hired the same time I was. ["The Railroad Trainmen's Journal," vol. IX, July 1892]
In short, a Hill-Billie is a free and untrammelled white citizen of Alabama, who lives in the hills, has no means to speak of, dresses as he can, talks as he pleases, drinks whiskey when he gets it, and fires of his revolver as the fancy takes him. ["New York Journal," April 23, 1900]
In reference to a type of folk music, first attested 1924.
Thra. What, if a toy take 'em i' the heels now, and they run all away, and cry, 'The devil take the hindmost'?
Dion. Then the same devil take the foremost too, and souse him for his breakfast! [Beaumont & Fletcher, "Philaster," Act V, Sc. 2, 1611]