Oh, a gambler walked into a bar
With an octopus in a great big jar
Set it down and said to the bartender, "Tell you what
I'll bet you a couple of beers
Against two free hours of work around here
My friend can play any instrument you got"

Well, the day was slow and the business light
And wouldn't pick up 'til later that night
So the bartender scratched his head and said, "Why not?"
So he walked up on that dark bandstand
Came back with a flugelhorn in his hand
Put it down and said, "Okay, play me something hot"

Then all of a sudden, that jar began to shake
And the octopus came slithering out like a great big wad of snakes

He grabbed that horn and rolled around
First on the bar, then on the ground
And the bartender said, "You lose," in a laughing voice
The gambler said, "No, he's just confused
It's those three valves he's seldom used
You see, a bugle is his instrument of choice"

Well, the octopus and the gambler drank their beers
Then octopus crawled back in the jar with a burp everyone could hear
The bartender said, "Now don't go away
I know I've got something that he can't play"
And he left for a minute and came back with a saxophone
The gambler said, "Double down this time"
And four more beers were set in a line
And the octopus crawled out and two beers were quickly gone

The patrons in the bar all gathered 'round
To see if that saxophone would emit the sound

Then he grabbed that sax and rolled around
First on the bar, then on the ground
'Til the bartender said, "Now do you wanna concede?"
The gambler said, "He's just feelin' it out
And before he puts that thing in his mouth
He needs a minute or two to moisten up his reed"

The octopus crawled back in the jar and the gambler drank his beers
The bartender, all frustrated, said, "Now wait a minute here
I'll bet you the deed to this whole bar
That slimy critter in that jar
Can't play an instrument that I've got in the back
And if you lose, the both of you
Will work for me doin' what I choose
For the next six months, now what do you say to that, huh?"
And the gambler said, "Well, buddy, you're on
Just bring out your sackbut or xylophone"
And the bartender said, "Oh, it's nothin' quite that trite"
And he went in the back and soon emerged
With the awful-est sound you ever heard
And laid down Great Highland Scottish bagpipes

Now the octopus must have thought those bagpipes glamorous
'Cause he caressed them in a manner clearly amorous

Then they began to roll around
First on the bar, then on the ground
'Til the bartender said, "Haha, I've got him this time, it's true"
The gambler said, "Oh, he'll settle down
And play it when he stops foolin' around
And figures out that playin' it is all he's gonna do"

Oh, the gambler and the octopus, they were the best, I swear
There was no other like them anywhere
Yeah, the gambler and the octopus, they were a winning pair
A straight royal flush could not compare

Well, it wasn't a fair bet because the gambler cheated
Yeah, the octopus was a graduate of Juilliard
And a member of the American Federation of Musicians
Yeah, and was also president of the Charlie McCoy fan club
Now you can hear him every night playing in the Gambler's Bar down on Lower Broad
Hey, bartender, eight more beers for my little buddy
If you please