A young, ferociously ambitious performer, Joey is a notorious cad. He’s a handsome, fast-talking and charming hustler, but he’s also a bit unrealistic, often getting ahead of himself. After landing an emcee gig on Chicago's South Side, he toys with the affections of a young woman and charms an important female patron of the city's elite. Brash, confident and deeply flawed, he somehow always lands on his feet.

A glamorous, dignified woman of high social class in Chicago, Vera Simpson is married to Mr. Simpson, the owner of a major bread company. She is a clever, quietly ruthless woman who doesn't miss a beat, and she usually stays a few steps ahead of Joey. Bored with married life, she enjoys being desired by a younger man like Joey, though she remains ambivalent about her feelings towards him.

An honest and good-natured young woman, Linda meets Joey outside of a pet store while looking at puppies. Though slightly naïve, Linda eventually catches on to Joey's lies. Still, she remains charitable and forgiving, hanging on to the glimmers of good she saw in him and helping him as a friend.

An embittered and bored chorus dancer in the Chicago vaudeville scene, Gladys was once severely slighted by Joey in an incident that sent her to the hospital. Incited by revenge, she and her old mobster friend Ludlow Lowell plot to profit from Joey and Vera's downfall.

A seasoned and sharp reporter who interviews Joey about the opening of his new nightclub, Melba has seen it all. Two sentences into their interview, she goadingly calls Joey out on his obviously fabricated origin story. But she remains unphased. After all, she’s interviewed all kinds of showfolk, including the surprisingly intellectual burlesque performer Gypsy Rose Lee.

A high-crime con artist and crook, Ludlow has earned a reputation on the South Side as an intimidating mobster. Scheming with Gladys Bumps, he convinces Joey to sign a deceptively one-sided contract making him Joey's "representative.”