Now we are getting to the nitty gritty of pure folk-rock Americana music – delivered by an almost entirely Canadian group formed in Toronto, Ontario. After their world tour with Bob Dylan in 1966 – where the Band helped shape what became known as folk-rock – they settled in Saugerties, New York, near Woodstock.

In a house called “Big Pink” in West Saugerties, they recorded the informal sessions that later became The Basement Tapes with Dylan. This is where they truly formed their own identity, leading to their 1968 debut album Music from Big Pink. So the tour and their time at Big Pink were really the inception of their Americana, roots-based sound – the one that would soon take the scene by storm.

Up on Cripple Creek was the first song performed in the legendary The Last Waltz, and it made an indelible impression on me. It was my first real foray into the group without Dylan. If there’s one magnificent introductory song that makes you sit up and take notice – especially if you’re unfamiliar with the Band – it’s this one. And it’s delivered by Levon Helm with that country-accented Arkansas drawl, full of vigor and grit.

You know right from the get-go this band – the Band – certainly know their stuff. They are just so tight. In terms of quality, I don’t think I’ve seen many bands reach the crescendo heights they achieved in their farewell concert on American Thanksgiving Day, November 25, 1976, at Winterland Ballroom in San Francisco.

I’m always left in awe when I watch it, wondering how they pulled it off – remembering so many songs, many of them by other famous artists, and playing with such precision for more than four hours. It’s hard not to think about what might have been lost if Martin Scorsese hadn’t filmed it. The thought of that is enough to make you shudder.

Up on Cripple Creek draws on music from the American South – rock and roll, country, and a touch of bluegrass. Lyrically, you get mentions of mountains, the Mississippi River, the Gulf of Mexico, and Lake Charles, Louisiana, where a girl named Bessie resides.

She tells him to come on by if there’s anything she can do. They head to the racetrack and have a flutter – and what do you know, Bessie wins. They split the winnings, but she throws hers in his face, just having a laugh. “That’s when that little love of mine
Dips her doughnut in my tea.”

He goes back out on the road to California but he says “this life of living on the road” is exhausting. He talks about going home to his “big mama,” but is tempted to return to Bessie again.

“This life of living on the road” suggest over-the-road trucking and ‘Big Mama’ also refers to their dispatcher over CB radio. Robbie Robertson does say below, the song is about a man who just drives these trucks.

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The following was abridged from Wikipedia:

Up on Cripple Creek is the fifth song on the Band’s eponymous second album, The Band. It was released as an (edited) single on Capitol 2635 in November 1969 and reached No. 25 on the US Billboard.

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 travelling 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.

[Verse 1]
When I get off of this mountain
You know where I want to go?
Straight down the Mississippi River
To the Gulf of Mexico
To Lake Charles, Louisiana
Little Bessie, girl that I once knew
She told me just to come on by
If there’s anything she could do

[Chorus]
Up on Cripple Creek, she sends me
If I spring a leak, she mends me
I don’t have to speak, she defends me
A drunkard’s dream if I ever did see one

[Verse 2]
Good luck had just stung me
To the race track I did go
She bet on one horse to win
And I bet on another to show
The odds were in my favor
I had ’em five to one
When that nag to win came around the track
Sure enough, she had won

[Chorus]

[Verse 3]
I took up all of my winnings
And I gave my little Bessie half
She tore it up and threw it in my face
Just for a laugh
Now there’s one thing in the whole wide world
I sure would like to see
That’s when that little love of mine
Dips her doughnut in my tea
He-he!

[Chorus]

[Verse 4]
Now me and my mate were back at the shack
We had Spike Jones on the box
She said, “I can’t take the way he sings
But I love to hear him talk”
Now that just gave my heart a throb
To the bottom of my feet
And I swore as I took another pull
My Bessie can’t be beat

[Chorus]

[Verse 5]
Now there’s a flood out in California
And up north it’s freezing cold
And this living on the road is getting pretty old
So I guess I’ll call up my big mama
Tell her I’ll be rolling in
But you know deep down, I’m kind of tempted
To go and see my Bessie again

[Chorus]

References:
1. Up on Cripple Creek – Wikipedia