Vince is a seventeen-year-old high school student trying to live an ordinary teenage life despite being born into a prominent Mafia crime family. He is smart, observant, and fiercely independent, determined to break away from the family business and become an upstanding citizen. His moral compass frequently clashes with the chaotic, violent realities of his relatives, yet he continually finds himself dragged into their underworld affairs.

Anthony Luca is a formidable mob boss and a strict, old-fashioned father. While he commands an empire of crime and is widely feared by his associates, he maintains a mild, reasonable demeanor at home. He constantly pressures Vince to show more motivation and join the family enterprise, spending his free time pursuing a clumsy but dedicated amateur carpentry hobby.

Vince's Mother is the fiercely domestic matriarch of the Luca family. She spends much of her time keeping the household functioning and enforcing a strict code of manners upon her children. She is obsessed with maintaining order and insists on regular family dinners, providing a facade of suburban normalcy amidst her husband's dangerous underworld profession.

Tommy is Vince's older brother, working enthusiastically as an enforcer for their father's criminal organization. Violent, impulsive, and significantly less academically gifted than Vince, Tommy fully embraces the mobster lifestyle. He struggles with his father's lack of trust in his judgment and requires handlers to keep him out of trouble.

Kendra is an intelligent, observant high school student who works as a reporter for the school journal and at a local daycare. As the daughter of an FBI agent, she leads a regimented life but harbors a rebellious, romantic streak. She shares a sense of being an outsider with Vince, making them unlikely confidants as they begin dating.

Ray Francione is an unusually calm and reasonable adult within the Luca family's criminal organization. Employed to act as a "babysitter" for Tommy, he approaches his chaotic job with a sense of cool detachment. This level-headed demeanor makes him an ideal confidant and mentor figure for Vince, who struggles to find sound advice elsewhere.

Alex is Vince's socially awkward best friend. Lonely and romantically frustrated, he relies heavily on Vince to help manage high school social situations, dragging him into activities like joining the football team to attract girls. Though sometimes self-absorbed and intensely jealous, he remains Vince's primary connection to the normal teenage world.

James Ratelli, known as Jimmy Rat, is a small-time business associate who owes Anthony Luca a significant sum of money. Desperate and terrified of the Luca family's enforcers, he ends up appealing directly to teenage Vince for an extension on his debt, drawing the boy further into the criminal underworld.

Ed is a coffeehouse owner and friend of Jimmy Rat who has fallen into severe debt with the Luca family due to his weakness for women. Like Jimmy, he is caught in a web of bad investments and mob intimidation, leading him to cross paths with Vince.

Uncle Pampers is one of Anthony Luca's fearsome enforcers, saddled with a silly nickname that belies the terror he inspires in debtors. Despite his frightening reputation, he possesses a surprising, soulful talent for singing country music.

Benny is an associate of the Luca family who drives a Cadillac. He is responsible for indirectly causing Vince's disastrous beach date by failing to provide his car for Tommy's enforcement job, though he later arrives at the right moment to provide a dramatic distraction.

Angela is a highly attractive high school student whom Vince takes on a carefully planned date. Her romantic evening is ruined when Vince discovers a live mob victim in his trunk, prompting her furious and immediate exit.