We can start out by thinking about the 1941 movie Tall, Dark, and Handsome. There are a couple possibilities - the film was popular enough to make the phrase into a cliche, or it was a cliche already and the title was playing off of it. While the film seems to have been reasonably popular, this seems to be a case of the latter.

The Oxford English Dictionary has citations of the phrase going back to 1906, but their list isn't exhaustive, and you can find the phrase in sources like the New York Times, the LA Times, and the Washington Post in the 19th century, back to the 1860s (here's a wedding announcement from 1888 in the NY Times that uses the phrase).

Interestingly, that Times citation is describing a woman, even though the cliche today is men-oriented (the OED's listing of a phrase even says "denoting a type of attractive man"), and other usages seem to suggest it was gender-neutral early on. The point where it became a cliche, and where it became gendered, appears to be with Mae West's usage of it to describe Cary Grant in the 1933 film She Done Him Wrong - a quote giving this explanation is specifically highlighted in the OED's listing. The movie was a hit (it also had Mae West's line "Why don't you come up some time and see me?" which made AFI's 100 Years, 100 Movie Quotes list), so it's not unbelievable, and Brewer's Dictionary of Modern Phrase & Fable (John Ayto and Ian Crofton, 2006) dates its status as a stock phrase to the 1930s, so that lines up.

As to the meaning, "tall" and "handsome" seem pretty self-explanatory, but "dark" is ambiguous. The film Tall, Dark, and Handsome starred Cesar Romero, who had Cuban and Spanish parents, and the NY Times citation I link above is also describing a Cuban woman. The Washington Post used it in 1900 to describe a Spaniard, and again in 1909 to describe an Italian man. That suggests there may be some "ethnic" component to it. However, Cary Grant was described that way, and he was a British-born actor. He was indeed tall and handsome, but his "darkness" seems to just be his hair and eye color. Given that he seems to be the cliche-making use of the phrase, it would suggest that that's what people consider "dark" in using the phrase, though dark hair and eyes often correlate with Hispanic ancestry anyway.

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