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US, mid-late 19th century, originally referring to then-recent stem-wind watches (invented in 1840s, commercialized initially 1850s by Patek Philippe & Co.).[1][2] These were expensive, top-notch watches, hence generalized (1892[3]) to “top-notch”, particularly applied to speeches, or to the orator in question. Non-speech senses later fell out of use. Nuance of “rousing” speech possibly by analogy with watch being wound up(“tighten by winding, excite, rouse”).[4]
Circa 2000, later sense of “interminable speech” a folk etymology, in sense “a speech that lasts so long one must wind one’s watch”.[1][2]
2000, Bill Schneider and Keating Holland, “What to look for Thursday at the Democratic National Convention”, August 17, 2000, CNN, “Clinton comparisons”:[2]
Or – heaven forbid – the Bill Clinton of 1988, who gave a tedious stemwinder in 1988 that has gone down in the books as the worst nominating speech in recent memory?
Note contradictory senses of “rousing speech” (earlier sense) and “boring speech” (later sense); use in the latter sense may be proscribed as a corruption, and is a folk etymology.