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[–] COFfeebreak 1 points (+1|-0)

"Up on Cripple Creek" was written by Band guitarist and principal songwriter Robbie Robertson, with drummer Levon Helm singing lead vocal.

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. Or he may not be cheating. Truckers also use the term "Big Mama" to refer to their dispatcher over the 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.

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."

That funky sound on "Up On Cripple Creek" was created by keyboardist Garth Hudson, who played a Hohner Clavinet D6 through a Vox Wah Wah pedal. The Band recorded most of the album "The Band" (their second) in Sammy Davis Jr.'s Hollywood house, which they rented out. "Up On Cripple Creek" was one of three songs they recorded at the Hit Factory studios in New York City.