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In the mornin' you go gunnin' for the man who stole your water
And you fire till he is done in but they catch you at the border
And the mourners are all singin' as they drag you by your feet
But the hangman isn't hangin' and they put you on the street
You go back, Jack, do it again, wheels turinin' 'round and 'round
You go back, Jack, do it again
When you know she's no high climber then you find your only friend
In a room with your two timer, and you're sure you're near the end
Then you love a little wild one, and she brings you only sorrow
All the time you know she's smilin'; you'll be on your knees tomorrow
You go back, Jack, do it again, wheels turinin' 'round and 'round
You go back, Jack, do it again
Now you swear and kick and beg us that you're not a gamblin' man;
Then you find you're back in Vegas with a handle in your hand
Your black cards can make you money so you hide them when you're able
In the land of milk and honey you must put them on the table
You go back, Jack, do it again, wheels turinin' 'round and 'round
You go back, Jack, do it again
And you fire till he is done in but they catch you at the border
And the mourners are all singin' as they drag you by your feet
But the hangman isn't hangin' and they put you on the street
You go back, Jack, do it again, wheels turinin' 'round and 'round
You go back, Jack, do it again
When you know she's no high climber then you find your only friend
In a room with your two timer, and you're sure you're near the end
Then you love a little wild one, and she brings you only sorrow
All the time you know she's smilin'; you'll be on your knees tomorrow
You go back, Jack, do it again, wheels turinin' 'round and 'round
You go back, Jack, do it again
Now you swear and kick and beg us that you're not a gamblin' man;
Then you find you're back in Vegas with a handle in your hand
Your black cards can make you money so you hide them when you're able
In the land of milk and honey you must put them on the table
You go back, Jack, do it again, wheels turinin' 'round and 'round
You go back, Jack, do it again
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But it is really about repeating bad choices in all different areas of. Fagen sings about the cycle (wheel spinning round and round) that one finds themselves in when they go back and repeat them again.
each verse describes a sinful or self destructive behavior i.e revenge, betrayal etc however I think the final verse describes the overall message of the song best. the phrases: " you swear and kick and beg that you're not a gambling man.." and "you're black cards make you money so you hide them when you're able" are about the way people hide and deny their sinful and deceptive natures. "in the land of milk and honey you must put them on the table." may, as one use pointed out refer to heaven however I think it may also refer to the pursuit of the promised land and that in that pursuit you must show your cards, meaning that to get ahead you must reveal your sinful nature.
I also think Gershwin cleverly used words that could have multiple meanings and interpretations to make the song more cryptic, such as "handle" possibly meaning booze, or slot machine handle.
In any case the song is definitely about how humans are incapable of avoiding sin and self destruction, returning to the same behaviors that they know will only cause pain and hardship.
...WHAT? Where you raised by wolves? Nevermind. We make a choice when we repeat behaviors. CHOICES. And some of us make the easiest of choices just because we can...then we're arrogant enough to pound on our chests and say that we made them because we're rebellious free individuals who buck societal expectations. What a fucking joke! And in reality, the person knows it's a joke. He's just a slacker who's happy taking the easiest path possible...
Personally I always thought it was about how we as humans do what needs to get done.
In the first verse, Jack loses an enormous amount of money, and in morning goes after the manager of the casino "the man who stole your water" . "Your water" is money. Things get out of hand "you fire till he is done in", and the manager calls the police "they catch you at the border". All the onlookers, the "mourners" clap and cheer as Jack is taken away by the police. The police release him "the hangman isn't hangin'". "Wheels turnin' 'round and 'round" is the roulette wheel calling him back for more and the dream of winning it big.
The second verse, "you know she's no high climber" is a game with a smaller jackpot that's "In a room with your two timer" which is the game played where all the money was lost. "Then you love a little wild one and she brings you only sorrow"...he's starting to win his money back, but then ends up losing again. "All the time you know she's smilin'" refers to overconfidence at winning, and how the house (she) always has the advantage.
The bottom line: Verse
1: When we make poor choices, and we do not appreciate the full force of the consequences, we will put ourselves into the same situations again.
Verse 2: Unless we admit that we don't know what we are doing, we will decieve ourselves into believing that next time things will be different.
Verse 3: You can lie to others, you can lie to yourself, but you can't lie when that monkey on your back gets hungry. You want to know if the monkey is still on your back? Walk by the produce store. I'll be damned if you don't come home with bananas.
You have and will continue to make the same stupid, yet dangerous, choices over and over again.