After a self-imposed exile, artist, Val Shepard, returns to New York City with the intention of picking up the life he left behind. With nowhere to go, he arrives on the doorstep of his ex-landlord and father figure, Jimmy Alfano. Jimmy is none too happy to see Val unannounced, and he lets Val know this. Annoyed with Val, but concerned over his wellbeing, Jimmy reluctantly offers him the Janitor’s closet across the hall from the studio Val abandoned when he left New York.
Cruising the Bars and Streets, Val soon learns that life on the Lower East Side has moved on without him. Looking to reconnect with the scene he visits the house of Madam Elsa Burgundy. She greets Val enthusiastically and introduces Val to Amiee. As Val and Amiee get better acquainted, they are interrupted by an argument in the hall outside their room where a man abuses a young girl. Val intercedes, and the man tells Val to move on and mind his own business. Unable to perform after his long trip, Amiee consoles him and allows him to stay for a while. She prepares a shot of heroin and asks Val if he’d like to try. He declines but asks her if he could watch while she shoots up. Before going on the nod, Amiee warns Val not to “stand on the sideline before it gets too comfortable.”
Val leaves Elsa’s house and returns to the bars of the Lower East Side, but nothing has changed, life has moved on without him.
Val begins to look for Jenna Bardi, the girlfriend he left without warning. After getting mislead by LES hustler Tommy Machine, Val has a chance meeting with Jenna, but Jenna wants nothing to do with him. Val tries explaining why he went, but Jenna tells him that it’s too late, she has moved on with her life. Val asks to see her one last time under the guise of obtaining closure. Jenna agrees to one final meeting at her new place for dinner that evening.
Upon arrival at her apartment, Jenna introduces Val to her friend Lara, and to Ian, Jenna’s new husband. (Ian looks suspiciously familiar to the man abusing the girl at Elsa’s house). Val is taken aback by the news of Jenna’s marriage. Further to add insult to injury, Val learns Ian is a successful painter and holding a show in a few months at the prestigious Turner-Prince Gallery. The same gallery where Val would have shown had he not sabotaged his career.
Val realizes he has lost Jenna, and as he is about to capitulate, Ian receives a phone call from his lover which instigates an argument between Jenna and Ian. While they argue, Val and Lara excuse themselves and leave.
Out on the street in front of Jenna's apartment, Val and Lara decide to go to a bar for a nightcap, and through their conversation, Val learns how Jenna met Ian.
Val takes a taxi back to the LES and has a philosophical discussion with the cab driver. Arriving home, Val walks into his building and hears Jimmy Hendrix’s Crosstown Traffic echoing through the stairwell. On his way to the top floor, Val passes two young girls entwined in a passionate embrace and several other people in various states of conjugation and altered consciousness.
Upon reaching the top, Val finds the source of the music is his old studio. Val enters to find a Warholesque party raging at full throttle. Val joins in and asks several people, whose party is this. He’s told, no other than Jackson King. Val looks for his neighbor and host to introduce himself, but Jackson King is nowhere to around. Val brings home a beautiful woman to his room, but before the two can perform, Val passes out.
The next morning Val wakes in bed up hangover. He rolls over and is startled by an unattractive woman. It is the same woman who Val left with last night, yet her appearance has changed as Val is now sober. While getting sick in his sink, the girl dresses, and asks Val or cab fare, Val reluctantly agrees. She tells him, “at least I asked first, if I had to take it, it would have been a lot more.”
While Val assembles himself, a young man wanders into his room. The man introduces Himself as Jackson King. Val tells him that he crashed his party last night. Jackson tells him that was fine, and he should have said hello. As Val tries explaining that he couldn’t find him, Jackson cuts him off to correct Val. “It wasn’t a party,” Jackson says, it was just some friends getting together and that even Val could recognize that. Val agrees obviously.
Val takes an immediate liking to Jackson, and the two go over to Jackson’s studio where they drink and talk. Val peruses Jackson’s collection of knick-knacks finding a piece of a Chagall mosaic. Knowing Jenna is a Chagall enthusiast, Val asks Jackson if he could buy the glass from him. Jackson gives Val the collage glass without charge. Jackson has another gift for Val, the paint brushes he left behind when he abandoned his studio. Seeing them, Val feels as if he is about to cry, but his ringing phone saves him from tearing up in front of Jackson.
Val returns to his room to take the call from the last person he was expecting, Jenna.
Val is surprised by the call and asks Jenna how she got his new number. Jenna tells him, from Lara, and she’s calling to make sure Val didn’t have the wrong impression, no matter what he heard Ian is not having an affair. Jenna must cut the call short and invites Val to lunch.
The next day over lunch Jenna apologizes to Val for putting him in such an awkward position. Val begins to explain why he did what he did. Jenna tells him it doesn’t matter. All dreams begin as they end and she is fine where she ended up.
Val tries to convince Jenna to leave Ian, it is less than a year, and he is already cheating on her. Jenna tells Val, there are only twelve covers of American Artist a year, just twelve! My husband is on the cover of September. Val takes out the Chagall Glass he was about to give to Jenna and then he stops. Jenna asks what he has. Val tells her it is nothing, just a piece of glass.
After lunch, Val throws the Chagall glass into the East River.
Val arrives at his home to find the police cordoning off the building with crime scene tape. Upon learning of his wife’s death, Ruta’s husband Peter tracked her down to Jackson’s studio. Thinking he was responsible for the death of his wife, Peter threw Jackson off the roof.
Val returns to Williamsburg and tracks down Ian and finds him on the street. The two men scuffle, and Val demands to know how Peter found out where Jackson lived. Ian tells Val everyone is better off with Jackson dead.
Jackson’s funeral is sparse. Apart from a few curiosity seekers, the only attendees are Jimmy, Val, and Jackson’s uncle, Jedidiah. After the funeral, they return to Jimmy’s, and the three men raise a toast, to Jackson King.
In the end, Val ascends the stairs to the floor where he supposedly lived with Jackson. He tries the door to his room, but the room is padlocked as it were in the opening scene. Val turns around and sees the door his old apartment open, and he walks in. All the splendor of Jackson’s apparent is gone. The room is bare and dilapidated. Val sits at his counter, his face is aged. Val begins to cook a shot of heroin as the screen fades to black.