Rambling, Gambling Willie (from "The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991" compilation)

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

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 gamblin'est 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

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

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

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

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

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

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