Risky Business

Joel Goodson is a successful high school student living with wealthy parents in Glencoe, Chicago. His father expects him to attend Princeton University, and Joel takes part in Future Enterprisers, creating small business projects with his classmates. His life is comfortable and high-achieving until he begins to seek more freedom.

Joel's parents go away on a trip, providing him with an opportunity to indulge in activities he normally wouldn't. With his newfound freedom, Joel raids the liquor cabinet and makes a scene in his house, dancing around to 'Old Time Rock and Roll' in his underwear. This night marks the beginning of his reckless adventures.

Joel's friend Miles contacts a prostitute named Jackie on his behalf, who turns out to be a male cross-dresser. Joel pays him to leave but is given the contact of Lana, a woman. This accidental encounter introduces Joel to a more intimate and complex relationship.

Joel is hesitant but ultimately calls Lana, with whom he spends the entire night engaged in passionate sex. This marks a turning point in his journey, venturing into adult relationships, far from his usual controlled lifestyle.

Lana asks Joel for $300 for her services, but when he returns from the bank, she has disappeared with his mother's expensive Steuben glass egg. Joel confronts Lana, demanding it back, leading to a confrontation with her pimp Guido, who pulls a gun.

Joel drives his father's Porsche 928 and is chased by Guido through Chicago streets. He eventually manages to escape, but the incident leaves him anxious about Lana and the situation with Guido.

Lana informs Joel that her belongings, including the stolen egg, are with Guido. She stays at Joel's house for safety, along with Vicki, another prostitute, until Guido's gang causes a confrontation on his lawn, forcing Lana and Vicki to leave.

Joel, Lana, Vicki, and his friend Barry get high on marijuana. During this chaos, Lana's attempt to retrieve her purse causes the Porsche to roll down a hill and into Lake Michigan, sinking the car and complicating Joel's plans.

To cover the costly car repairs, Joel and Lana set up a makeshift brothel at his house, hosting a large party with friends and Lana’s coworkers. The event is a major success but coincides with an interview from Princeton, which is disappointing.

The Princeton recruiter, Rutherford, is unimpressed due to interruptions, while Joel's house turns into a lively party. Afterward, Joel and Lana share an intimate moment on an 'L' train, symbolizing their complicated relationship.

Joel returns home to find his house has been burglarized; his mother notices a crack in her stolen egg. Despite setbacks, Joel manages to restore his home before his parents return, preserving his status with the Princeton interview behind him.

Joel's father congratulates him, sharing that the Princeton interviewer was impressed, and Joel is accepted. This symbolizes a pragmatic acknowledgment of his achievements amid his chaotic experiences.

Joel and Lana meet at a restaurant, reflecting on their relationship and future. Lana expresses her desire to continue seeing him, hinting at ongoing complications and feelings between a young man and an elusive woman.