Following a string of failures, revered filmmaker Harry Stone returns to New York City after several years in France and decides to take on a more commercial science-fiction screenplay titled The Pickle. In a meeting with young studio executive Ronnie Liebowitz, Harry learns the script is about a group of Midwestern teenagers who grow an enormous cucumber and use it as a space vessel to fly to another planet. Although certain the project will ruin his career, Harry is eager to collect the generous paycheck being offered and agrees to begin production immediately. While staying at the Plaza Hotel, an adoring fan named Bernadette propositions Harry for sex, but they are interrupted by a telephone call from his ex-wife, Ellen. Harry meets Ellen in the hotel restaurant to discuss their daughter, Carrie, who has recently given birth. Ellen asks for more alimony payments, and Harry questions why they ever ended their relationship. Later, Harry’s twenty-two-year-old French lover, Francoise Tournier, unexpectedly arrives just before he leaves to visit his daughter. When Francoise teases him about The Pickle, Harry becomes irate and demands she go back to Paris. They reconcile in the limousine on the way to see Harry’s mother, Yetta, and Francoise forces Harry to watch a cut of The Pickle before its official preview screening the following day. As they drive through familiar neighborhoods, the director remembers visiting his grandparents’ general store on the day of President Franklin D. Roosevelt’s death. As Francoise returns to the hotel, Harry laments the loss of funding for one of his passion projects, a modern adaptation of Leo Tolstoy’s Anna Karenina. Outside Yetta’s nursing home, the sight of the boardwalk Ferris wheel triggers memories of his parents’ turbulent marriage. He decides to visit his childhood home, which has fallen into despair, and begins telling the new tenants about the premise of The Pickle. Back at the Plaza Hotel, Harry fights with Francoise about her presence in New York, but quickly apologizes and spoon-feeds her a hot fudge sundae during an interview with a newspaper reporter. Agent Phil Hirsch interrupts, as does Harry’s son, Gregory, a recovering drug addict. After postponing the rest of the interview, father and son have Harry’s blood pressure tested and see a lounge performance by his other ex-wife, Patti Wong. While becoming intimate with Francoise, Harry suffers what he believes to be a heart attack, but the house doctor diagnoses it as indigestion. The next morning, Harry goes to his ex-wife Ellen’s apartment and proclaims that he wishes to re-marry. When she refuses, he climbs onto the balcony and threatens to jump until she promises to go to bed with him. In a lunch meeting, Ronnie Liebowitz and marketing executive Mike Krakower assure Harry that audience polling for The Pickle has been surprisingly high. They begin swapping ideas for the director’s next picture—an epic adventure about Hernán Cortes and Montezuma—but the conversation turns sour when the executives suggest updating the story to a present-day barrio in East Los Angeles. Afterward, Harry sits alone and watches more footage from The Pickle, and reminisces with projectionist Butch Levine, who is a former childhood classmate. Before the premiere screening of The Pickle, Harry’s family and associates throw a party, but Harry stays behind in his hotel room, insisting he never attends the previews for his own films. Once he is alone, he swallows several pills while recording a goodbye message to his loved ones to be played after his suicide. He falls unconscious, but awakens when Butch Levine calls to inform him that the screening is going well. After regurgitating the remainder of the medicine, Harry rushes to the theater to hear the audience’s enthusiastic praise. Although Ronnie Liebowitz agrees to greenlight the Cortes and Montezuma film, Harry instead suggests a black-and-white drama about a father and son, which parallels his own career comeback since returning to New York. Looking up into the sky, Harry envisions his younger self aboard the “Pickle” spacecraft as it hovers over the marquee and twirls upward into the starry night.