In the late 1940s, a struggling novelist named Jack Kerouac and his two friends, Neal Cassady, a former reform school delinquent, and a poet, Ira Steiger, live in Greenwich Village, New York City. One day, Neal invites Jack on a road trip to San Francisco, California. In Iowa, Neal’s girl friend, Stevie, joins them. In San Francisco, Neal visits an old childhood friend, Dick, who is studying at the San Francisco Art Institute. When Dick introduces Neal and Jack to his girl friend Carolyn, she is intrigued because they are unlike any men she has previously known. By day, Carolyn continues art classes, Neal sells blood to pay the rent, and Jack works on his novel. At night, the three friends frequent Bud’s Bop Shop, a local jazz club. As Jack and Carolyn dance, Jack reveals that Ira’s nickname for Neal is “the Adonis of Denver,” hinting that Neal likes to romance men and women, depending on his mood. Back at their apartment, Stevie accuses Neal of having an affair with Carolyn “the debutante,” and Neal makes love to Stevie to diffuse her anger. Meanwhile, Neal does his best to dissuade Carolyn from accepting Dick’s marriage proposal. Later, Jack says that he is ready to move back to New York City, and wants Carolyn to join him. As Jack walks in the rain, he sees Carolyn step into Neal’s car. While Carolyn and Neal make love, Jack hitchhikes back to New York City alone. Stevie leaves Neal for other adventures, while he finds work as a train conductor. Although Neal and Carolyn write to Jack, he ignores their letters. In New York City, Ira presses publisher Mr. Ogden to accept Jack’s manuscript, but when Ogden rejects it, Ira suggests he and Jack try their luck in San Francisco. There, Ira stays with Neal and Carolyn, while Jack works at dead-end jobs and avoids his friends. Over Chinese food, Ira confesses that he loves Neal. Carolyn becomes uncomfortable and leaves the restaurant. Neal chases after Carolyn, and assures her of his love. Later, Neal has sex with several men in the jazz club restrooms, and then wanders through the seedy part of town. Neal discovers Stevie entertaining a sailor, but he scares him away and makes love to her. Meanwhile, Carolyn becomes depressed and remembers how Jack warned her not to expect too much from Neal. At sea, Jack toils as a ship’s cook, then as a migrant worker while he writes. When Carolyn finds Neal in bed with Ira and Stevie, Neal tries to explain, and Carolyn says that she is pregnant. She slaps Neal and then leaves, but later, convinces Neal to move to the suburbs in anticipation of the baby’s birth, and he proposes marriage. Later, Carolyn invites the neighbors, Bob and Betty Bendix, to dinner, but it is an awkward evening. Meanwhile, Jack refuses to take another dead end job and locates the Cassadys in the suburbs. At a bar, Neal admits that married life is hard. When Jack asks if Carolyn ever mentions him, Neal confesses that she talks about Jack whenever he makes a mess of things, which is often. Neal invites Jack to be a houseguest. Then, the men visit a nightclub, while Carolyn wonders where Neal has gone. When the friends return in the morning, Neal goes to work and Carolyn confesses that she is tired of Neal treating her like garbage, and Jack comforts her. Neal later apologizes, and disappears with Carolyn behind closed doors. Soon, Neal and Jack agree to take turns being Carolyn’s husband. Later, Neal decides to take a trip alone to Mexico, and says that Jack is the only thing keeping the Cassadys’ marriage together. One day, after ten years Ogden telephones Jack with an offer to publish his novel On the Road, based on his road trip with Neal and Stevie. Jack travels to New York City, where he promotes his novel on television. Neal is threatened by Jack’s new celebrity status, despite Jack’s assurances that his success is good for everybody. Carolyn claims that the notoriety of the book turns the lives of Jack and Neal into “an open book.” Soon, Neal and a literary fan are arrested for possession of marijuana. Jack wants to help his friend, but Ogden warns him not to get involved. Neal is sent to prison, but after his release, he joins writer Ken Kesey and his Merry Pranksters as they tour the country in a bus on a quest to make art out of everyday life. Although Neal and Jack are joined in literary history, in life they drift apart. When Jack returns to San Francisco on business, he hitchhikes to visit Carolyn, and asks her what he and Neal did wrong. She replies that they did nothing wrong, they just did it first.