Benji is a 15-year-old Black teenager who lives in Manhattan during the school year and spends his summers in Sag Harbor. Anxious and observant, he attempts to rebrand himself as "Ben" over the summer of 1985 to appear cooler and more mature. He works making waffle cones at the local Jonni Waffle ice cream parlor and constantly analyzes his social environment to find authentic ways to act.

Reggie is Benji's 14-year-old brother. Often treated as Benji's twin when they were younger, he begins to assert his independence this summer by walking instead of biking and choosing different teams during games. He works at Burger King and schedules his shifts carefully to avoid his parents on the weekends.

A successful podiatrist who grew up facing adversity in the inner city. He struggles with alcoholism and a volatile temper, frequently subjecting his family to verbal abuse that drives his children out of the house. He actively wants his sons to be tough, aggressively teaching them to fight back against perceived slights in the world.

A successful lawyer whose parents helped establish the Azurest community in the 1940s. She looks forward to summers in Sag Harbor, where the environment makes her look and feel younger. Her joy and confidence routinely vanish behind closed doors when confronted by her husband's intense verbal abuse.

The college-aged older sister of Benji and Reggie. She maintains a cool, downtown persona and limits her visits to the Sag Harbor house to escape the family's severe domestic tension. Having previously acted as a babysitter and boss to her brothers, she advises Benji to leave the house as soon as he is old enough.

A core member of Benji's summer friend group. He wears bright white Filas, frequently exaggerates or lies about his exploits, and believes the racial divide in America is a state of perpetual warfare. He attempts to scheme his way into an 18-and-older concert by bribing a bouncer with free ice cream.

A friend of Benji who gains access to a car, granting the group new mobility across the island. He adopts a militant racial consciousness but readily accepts financial support from his mother's mainstream corporate job. He works alongside Reggie at Burger King.

A teenager in the summer crew who owns both a car and a BB gun. He instigates target practice in an abandoned parking lot and initiates the subsequent BB gunfight where he accidentally shoots Benji near the eye.

A member of the friend group who frequently becomes the target of teasing. Without a spot in the car, he must pedal his bike to meet the others. He argues passionately with Benji over music tastes, accusing Benji of favoring white artists.

A teen in Benji's social circle who attends basketball camp late in the summer. He pulls Benji to safety when Benji panics in the water and later encourages him to try shooting the BB gun during target practice.

The Dominican owner of the local Jonni Waffle ice cream parlor. He hires primarily Black workers, prompting his teen employees to constantly debate his own racial background based on his walk and physical features.

A year-round Sag Harbor resident who works at the ice cream shop. He embraces loud 1980s Black fashion trends, carries a massive radio that commands attention, and dates Melanie.

An employee at the ice cream parlor who sports a distinct New Wave haircut. She works alongside Benji, who harbors a quiet, constant attraction to her as they navigate the busy customer rushes.

A girl who returns to the summer friend group and immediately dates Nick. She shares a nostalgic moment and a brief kiss with Benji while breaking into his old childhood house, prompting Benji to reflect deeply on his past.

Benji's uncle, who is estranged from his own father. He agrees to buy beer for Benji and his friends in exchange for a ride to the Sag Harbor Hills neighborhood, where he points out his childhood home from the street without going inside.

A newcomer who arrives at the end of the summer without clear ties to the local families. He aggressively bullies younger children at the Labor Day party and recklessly throws patio furniture into the community bonfire.

A French student at Benji's Manhattan prep school. He mocks Benji's race, prompting Benji's father to demand that Benji retaliate physically to prove he is not soft.