A poor young man is finally able to achieve his dream of running a horse at the track, but when he starts becoming successful, he begins to lose sight of what mattered to him before.

Raised by Natalie Brennan, a flamboyant and irresponsible mother, Ziggy Brennan gets involved in hustling men at a young age. She hangs around with a wild crowd and learns gets her "street smarts" first from her mother, who wants everyone to think they are sisters, and then from Denny Reagan, an older man. He starts teaching her his tricks of the trade and she falls right in line with his crooked ways. Then one night she meets Martin J. 'Mart' Neilson, a tall, handsome, honest farmer boy who's a sailor and they fall in love. While he's away fighting the war, she discovers she's pregnant.

In the gay '90s, cardsharps take over a Mississippi riverboat from a kindly captain. Their first act is to change the showboat into a floating gambling house. A ham actor and his bumbling sidekick try to devise a way to help the captain regain ownership of the vessel.