In 1964 on Chicago's Near-North Side, Preach – an aspiring playwright – and Cochise – an all-city basketball champion – are best friends who are both celebrating the final weeks of their senior year with their classmates at Edwin G. Cooley Vocational High School. While sitting in class, Cochise sleeps while Preach comes up with the idea that Pooter, another classmate and friend should fake a nosebleed, so they can get out of class. As Preach and Pooter leave with the teacher's permission, Cochise, who's now awake, sneaks out the classroom's back door.
After getting out of class, the trio meet up with another classmate who's sitting outside the school. The group then hitch a ride from school by hanging on the back of a city bus. The group end up at Lincoln Park Zoo where they spend the day stealing snacks from the concession stand and antagonizing animals.
After spending a few hours at the zoo, the group heads back to the neighborhood via train. Once back, the group shoots a few basketball hoops with some locals before Pooter states he needs to return to school before closing to retrieve his books. The group ends up at Martha's, a local hangout where they run into another classmate on their way inside, Dorothy who is giving a "Quarter" party at her house later that evening. While inside, Preach is shooting dice with two guys from the neighborhood, Stone and Robert.
During the dice game, they encounter one of Preach's classmates, Brenda in whom Preach shows an immediate interest. After Preach is chased out of the hangout by the owner for gambling, the group then splits up. Cochise arrives home, where he learns via mail that he has received a basketball scholarship to attend Grambling State University. The group meet up and binges on alcohol, celebrating Cochise's scholarship before heading off to Dorothy's house party.
Once at the party, Preach encounters Brenda again, who has no interest in him. While the party is going on, Preach retreats to a bedroom where Brenda is and the two discuss love poems. The party ends abruptly when another classmate named Damon shows up and spots Cochise dancing with his girlfriend, Loretta. This leads to scuffle between the two.
Having trashed the house during the scuffle, the group retreats back to Martha's. The group, which consists of Cochise, Preach, Pooter and Tyrone, encounters Stone and Robert. The pair ride up in a Cadillac and convince Cochise and Preach to go for a joyride with them, driving through the neighborhood, downtown Chicago and the Gold Coast area with Stone at the wheel.
Preach convinces Stone to let him drive, which leads to attention from the police due to his bad driving. A chase leads from downtown into a garage at Navy Pier, in which they get away from the police, only to end up hitting a parked car with occupants inside. After the accident, they flee the vehicle: Preach and Cochise running in one direction and Stone and Robert in another.
The next day, Cochise, Preach, Pooter, Tyrone, and Willie all decide to go the movies. However, the group is short on cash. Preach and Cochise approach two prostitutes, pretending to want countless sexual services. Later, they are both stating they are actually cops. While searching and threatening to arrest them, one of the women pays $10 to Preach to be let go. The other one notices that the police badge is a fake. After realizing their scam is blown, the two run off with the money.
The group then ends up at the movie theater where they watch Mothra vs. Godzilla. Cochise, Tyrone, and Preach are with their girlfriends, while Pooter is left venturing around the theater by himself. Upon finding a seat, he bumps into a man who gets confrontational. Another man intervenes on Pooter's behalf, which leads to a brawl between the Disciples and the Counts street gangs in the theater. The following day, Preach and Brenda spend a day together which leads to their having sex back at Preach's house. After learning that Cochise and Preach had an inside cash bet on Preach hooking up with her, Brenda leaves the house upset.
The following day at school, Cochise and Preach are arrested for being in the stolen car and are charged with grand theft auto. While at the station, the pair are reunited with Stone and Robert who are also being questioned. Mr. Mason, the boys' history teacher, persuades the police to release Preach and Cochise because of their clean record. Both Stone and Robert remain imprisoned due to them being repeat offenders.
Confused as to how they were let off the hook early, Preach and Cochise leave the holding area. Thinking that Preach and Cochise placed all the blame on them, Stone and Robert immediately hunt for both of them after being released from jail a few days later. While in school, Preach learns that Mr. Mason actually got them out of jail. He sets off to look for Cochise to tell him the information. In his pursuit of looking for Cochise, Preach runs into Cochise's cousin Jimmy Lee who takes him to his apartment. Once there, Preach finds him with his ex-girlfriend. Preach becomes angry and leaves.
Preach then retreats to Martha's. Spotted by Damon, he walks over to a table where Brenda is sitting and begins to apologize. While talking to Brenda, Preach overhears Damon speaking to Stone and Robert who have just walked into the hangout. As he sends Brenda out of the restaurant, urging her to meet him at the train station in 15 minutes, he tries to sneak out the back.
Preach's presence is then made known by Damon. Stone and Robert began taunting and chasing Preach around the restaurant. After spotting the confrontation, the hangout's owner intervenes. She forces both Stone and Robert out of her place with a meat cleaver while Preach is hiding in the restroom. Preach tries to sneak out the side door but is spotted by the pair who are waiting for him outside.
After evading them, Preach meets up with Brenda, where he learns from her that Cochise went to Martha's looking for him. Stone, Robert, and Damon ultimately find and catch Cochise on a side street. Together, the vengeful trio corner him and beat him severely, leaving him to die. Having been notified of the attack on Cochise, Preach frantically searches the streets. He finds his best friend's lifeless body lying face down under an overpass. Using Cochise's untimely death as motivation and inspiration, Preach runs off after the funeral to pursue his dream of becoming a renowned Hollywood poet and writer. This ultimately makes both him and his newfound guardian angel proud.
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