"Up on Cripple Creek" is notable as it is one of the first instances of a Hohner clavinet being played with a wah-wah pedal. The riff can be heard after each chorus of the song. The clavinet, especially in tandem with a wah-wah pedal, was a sound that became famous in the early to mid-1970s, especially in funk music.
Robbie Robertson said of writing the song: I had some ideas for 'Up on Cripple Creek' when we were still based in Woodstock making Music From Big Pink. Then after Woodstock, I went to Montreal and my daughter Alexandra was born. We had been snowed in at Woodstock and in Montreal it was freezing, so we went to Hawaii, really as some kind of a way to get some warmth, and to begin preparing for making our second album. I think it was really pieces and ideas coming on during that traveling process that sparked the idea about a man who just drives these trucks across the whole country. I don’t remember where I sat down and finished the song, though.
Drawing upon the Band's musical roots—the American South, American rock and roll, and bluegrass/country—the song is sung from the point of view of a truck driver who goes to Lake Charles, Louisiana, to stay with a local girl, Bessie, with whom he has a history. In the song, he gambles, drinks, listens to music, and spends time with "little Bessie," who takes an active role in the goings-on, while expressing her opinions, further endearing herself to the narrator. At the end of the song, after exhausting himself on the road, he talks about going home to his woman, "big mama," but is tempted to return to Bessie again. He may or may not be cheating. Truckers also use the term "Big Mama" to refer to their dispatcher over CB radio. Concerns about the weather in other parts of the country and the line "this life of living on the road" suggest over-the-road trucking. At the start of the song he's hauling logs off a mountain and at the end he may be weighing options: "rolling in" to home base for a new cargo or seeing his Bessie again.
One verse has the singer and Bessie listening to and commenting on the music of 1940s and 1950s bandleader Spike Jones. Robertson said of Jones, "I was a Spike Jones admirer. I thought the way that he treated music was a healthy thing. He could take a song and do his own impression of it that was so odd and outside the box – and in many cases hilarious. I liked him a lot.”
Robertson has said of the song: We're not dealing with people at the top of the ladder, we're saying what about that house out there in the middle of that field? What does this guy think, with that one light on upstairs, and that truck parked out there? That's who I'm curious about. What is going on in there? And just following the story of this person, and he just drives these trucks across the whole country, and he knows these characters that he drops in on, on his travels. Just following him with a camera is really what this song's all about. From: https://en.wikipedia.org/wiki/Up_on_Cripple_Creek
