Do It Again - Steely Dan

"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."

I picture this part as a Western.
He wakes up early to go after the man who stole from him. He hunts him down, finds him and then guns him down. He tries to escape, but the sheriff catches him before he crosses into Mexico. The funeral for the dead person isn't even over yet and they drag him to his lynching. But his sentence is commuted, and they let him go.

"You go back, Jack, do it again, wheels turinin' 'round and 'round
You go back, Jack, do it again."

The man is in a vicious cycle of making mistakes and then not learning from them. This anticipates how, in the rest of the song, he will keep messing up over and over 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."

He finds his gold-digging loser girlfriend having sex with his best friend. Desperate, he finds another crazy girl to have a relationship with. She makes him very unhappy, but she looks good, and she knows that he will come back to her no matter what she does to him.

"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 bring you money so you hide them when you're able
In the land of milk and honey you must put them on the table."

He pleads with his friends to take a trip to Vegas, that he promises he won't gamble away all his money again. They give up and take him. He takes not only a gun with him but also hides some cards, as he will also be cheating in Poker. He knows he can win big this way. This time, he will make it. So he tells himself.