Green’s Dictionary of Slang

describing a person or thing that is superlative, unique, extraordinary, usu. positive but occas. negative.

1828		Western Monthly Rev. June 15: The snapping turtle, the ring tailed painter, the best horse, dog and gun, &c. have been successive additions [DA].
1909		Eve. Star (Wash., DC) 1 Aug. 31/3: A couple of old ring-tailed galoots who’ve shirked all their lives.
1912		R.W. Brown ‘Word-List From Western Indiana’ in DN III:viii 587: ring-tail leader, n. The leader of the leaders; ring-leader ‘You ought to get him; I think he is the ring-tail leader’.
1921		Wash. Times (DC) 29 Jan. 16/4: The Smithsonian Institute will toss one of Paine’s ringtailed spasms at the moon just as soon as the weather gets balmy.