Songfacts®:

• A Silver Cloud is a Rolls Royce, a high-end luxury car. In the song, Loudermilk walks into a Rolls dealership wearing boots and blue jeans. He asks to drive the Silver Cloud and is rebuffed, but when he shows the manager all his cash, he's suddenly granted the test drive and treated with respect.
  
  The song was written by Gordon Lightfoot, inspired by Ronnie Hawkins, whose backing band The Hawks later became The Band. Hawkins is from Arkansas but was living in Toronto, where he got to know Lightfoot. He had a few hit singles in Canada, so money was pouring in. But Hawkins kept his ragged look, belying his financial status. According to a story on Hawkins published in The Canadian in 1976, the story of the song is true, with a few details changed. Hawkins did indeed ask for a test drive and was shown the door. The car cost $18,500, so he left, went to the bank, and took out that amount in cash. He went back into the dealership, poured the money on the floor and said he was buying the Silver Cloud. He asked the sales manager what the commission would be on the sale, and was told $1500, so Hawkins took that amount out of the pile and kept it, since the salesman didn't earn it.
• Gordon Lightfoot was just getting started as a songwriter and singer at this time. His songs "For Lovin' Me" and "Early Morning Rain" were recorded by Peter, Paul & Mary in 1965, and in 1966 he released his first album, Lightfoot! "Talkin' Silver Cloud Blues" was released by John D. Loudermilk, who was best known as a songwriter; his compositions include "Tobacco Road" and "Indian Reservation (The Lament of the Cherokee Reservation Indian)."
• The title is a play on Bob Dylan's "Talkin' John Birch Paranoid Blues." Lightfoot and Dylan were friends and had the same manager, Albert Grossman. Lightfoot was on the bill for the 1965 Newport Folk Festival when Dylan famously plugged in.
• According to Ronnie Hawkins, he asked the Rolls Royce salesman if the dashboard was real wood and, when told it was, said, "Is there a termite warranty?" This part of the story comes around at the end of the song when the car breaks down and there are "termites running around and around on my dashboard."
• The song states the moral as "never judge a man by the way he is dressed," but it's also a parable on materialism. The singer only wants a Rolls Royce because he already bought a Cadillac and still has money to spend. He'll just keep wanting something more expensive and with more status, and will never truly be satisfied.