Bob Dylan

Released: March 26, 1991

Songwriter: Bob Dylan

Producer: John Hammond Tom Wilson (producer)

[Verse 1]
Come around you roving’ gamblers and a story I will tell
About the greatest gambler, you all should know him well
His name was Will O’Conley and he gambled all his life
He had twenty-seven children, yet he never had a wife
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gambling now, nobody really knows

[Verse 2]
He gambled in the White House and in the railroad yards
Wherever there was people, there was Willie and his cards
He had the reputation as the gamblingest man around
Wives would keep their husbands home when Willie came to town
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gambling now, nobody really knows

[Verse 3]
Sailing’ down the Mississippi to a town called New Orleans
They’re still talking’ about their card game on that Jackson River Queen
“I’ve come to win some money,” Gambling Willie says
When the game finally ended up, the whole damn boat was his
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gambling now, nobody really knows

[Verse 4]
Up in the Rocky Mountains in a town called Cripple Creek
There was an all-night poker game, lasted about a week
Nine hundred miners had laid their money down
When Willie finally left the room, he owned the whole damn town
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gambling now, nobody really knows

[Verse 5]
But Willie had a heart of gold and this I know is true
He supported all his children and all their mothers too
He wore no rings or fancy things, like other gamblers wore
He spread his money far and wide, to help the sick and the poor
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gambling now, nobody really knows

[Verse 6]
When you played your cards with Willie, you never really knew
Whether he was bluffing or whether he was true
He won a fortune from a man who folded in his chair
The man, he left a diamond flush, Willie didn’t even have a pair
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gambling now, nobody really knows

[Verse 7]
It was late one evening’ during a poker game
A man lost all his money, he said Willie was to blame
He shot poor Willie through the head, which was a tragic fate
When Willie’s cards fell on the floor, they were aces backed with eights
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gambling now, nobody really knows

[Verse 8]
So all you roving’ gamblers, wherever you might be
The moral of the story is very plain to see
Make your money while you can, before you have to stop
For when you pull that dead man’s hand, your gambling days are up
And it’s ride, Willie, ride
Roll, Willie, roll
Wherever you are a-gambling now, nobody really knows

Bob Dylan (born Robert Zimmerman May 24, 1941), is an American singer-songwriter, writer, and artist who has influenced popular music and culture for more than five decades. Dylan has especially played a critical role in the American folk music revival.

Dylan’s songs are built from myriad political, social, philosophical and literary influences. Many of his anti-war and civil-rights-influenced songs set social unrest, as journalists widely named him the “spokesman for his generation” in the 1960s.

The musician has a signature change in voice and style in many different albums of his throughout the decades. He has notably explored and experimented with the genres of folk, rap, blues, and rock.

more tracks from the album

The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991

From the albums

Bob Dylan popular songs

Rambling Gambling WillieBob Dylan

Bob Dylan

The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991