I’ve strode the headwaters of Route 66 many many times: Michigan & Adams in Chicago, about 100 paces from the front door of Orchestra Hall.
Bobby Troup’s song has been done to great effect by many groups. Of the ones I’ve heard, I think I like the 1960 reading by the Four Freshmen best. (That recording is not on YouTube, as far as I can tell.)
Bobby of course was the Doctor on the “Emergency!” TV series, performing with Julie London, his off-screen wife. Julie was formerly married to Jack Webb, who ironically was the producer of “Emergency!”
Having only briefly glimpsed Bobby’s character on that TV series, I didn’t have too clear an idea of his appearance, especially in his heyday as a song writer in the 40’s and 50’s.
Well, about twenty years ago I was watching an old Perry Mason episode, made ca. 1960. Some of the action was set in a ‘beatnik’ nightclub, where Perry had to visit a musician/poet. The guy was dressed a little like a beatnik and I think he was wearing a little goatee. I don’t recall why the thought occurred to me, but I said to myself, “I think that character is being played by Bobby Troup.” I made sure to catch the end credits, and sure enough, it was. He did change a lot in the 20 years or so between that Perry Mason episode and his gig on Emergency!.
He also had a bit role in the original M*A*S*H movie.