Hi, Roger - I think this is my favorite Cole Porter song - I love this style of humor. Here's what David Ewen says in American Popular songs: From the Revolutionary War to the Present:

A number written for the private delectation of Cole Porter's friends. He improvised it one evening in 1934 during a party at the home of a friend. Monty Woolley proceeded to borrow a morning coat and a silver tray and impersonated a butler while delivering the lines to Porter's accompaniment. For the rest of that season Woolley enjoyed nothing better than to arrive at parties dressed up as a butler; always upon his entrance he would chant the first line of "Miss Otis Regrets." He sang it in the Cole Porter screen biography Night and Day in 1946.

So it seems to me that Porter wrote it simply for the fun of it, and that there's no deep meaning or complicated history to it. Ah, but when Ella Fitzgerald sang it, her voice was pure silver.

Here's what Robert Kimball says in The Complete Lyrics of Cole Porter

Porter wrote this as a parody of a country and western song, and dedicated it to Elsa Maxwell. Monty Woolley suggested the title to Porter, which he accompanied with a wager that Porter could not write a song to fit the title. It was first performed on stage by Douglas Bing in the London production of Hi Diddle Diddle that opened on October 3, 1934.

Now, I wonder what country song he was parodying....
-Joe Offer-