Guitarist Robbie Robertson wrote this song, which tells a disjointed story about a mountain man and a girl named Bessie. We hear about a trip to the horse races, listening to Spike Jones, and how what really makes him happy is when she "dips her doughnut in my tea."
Like many songs by The Band, it's wide open for interpretation. Robertson claims he doesn't even know what's going on. "I don't really write songs with anything other than just a storytelling sense," he said when asked about the song in Goldmine (August, 1998). "You sit down and write the song, and usually when something happens, you just don't even know where it came from, or why it came, or anything like that. That's the best. You know, when something comes out of you that surprises you. And it was one of those. You know, I was just sitting down to see if I could think of anything, and that's what came out. But it was a fun song to write."
Drummer Levon Helm sang lead on this track, giving it a very folksy vibe.
The guy in this song is one of the many curious characters Robbie Robertson has conceived. "We're not dealing with people at the top of the ladder," he said. "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."
Robertson is listed as the only songwriter on this track, which is something his bandmates disputed, as they claimed they helped write it. Songwriting credits going to Robertson was a great source of friction in The Band.
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 (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.
In The Band's 2000 Greatest Hits compilation, Levon Helm said, "It took a long time to seep into us. We cut it two or three times, but nobody really liked it. It wasn't quite enough fun. Finally one night we just got hold of it, doubled up a couple of chorus and harmony parts, and that was it."
The Band performed this on The Ed Sullivan Show in 1969. It was their only appearance on the show.
The rap duo Gang Starr sampled this on their 1990 track "Beyond Comprehension."