Jolene Jessica Chastain is a fifteen-year-old orphan who breaks free from foster care and marries Mickey Zeberiah Newman, a nerdy 20-year-old, hoping for a new beginnings. They settle with Mickey’s Uncle Phil Dermot Mulroney and Aunt Kay Theresa Russell, pooling their limited resources as Jolene adjusts to a life she hadn’t anticipated. On the night before her sixteenth birthday, Jolene asks Mickey about his mother, but he rebuffs her and begins to cry. To soothe him, she seduces him, yet his inexperience makes the encounter feel uneasy and joyless. The next day, as Jolene’s birthday approaches, Phil and Kay treat Jolene with a mix of routine tenderness and awkward arousal. Phil is moved by Jolene’s dancing while he cleans the floor, and the pair engage in a secret affair, with Phil promising to build a house for them but insisting that their relationship remain concealed because they are both married. When Kay discovers them, she forces Jolene out of the house. A subsequent altercation with Phil follows, and Mickey drives away, ultimately ending his life by jumping off a bridge. The tragedy fractures the family and sets Jolene on a perilous path.
Aunt Kay places Jolene in a juvenile mental institution, where she meets Cindy [Frances Fisher], a psychiatric nurse who becomes deeply entangled with Jolene. Jolene, a naturally gifted artist, longs for drawing materials; her wish for paper and colored pencils is denied, but she is allowed crayons and begins making a small business out of crayon portraits for fellow patients. Jolene is called to testify against Uncle Phil, who is sentenced to eighteen months in prison for statutory rape. Cindy, who is a closeted lesbian, quickly develops feelings for Jolene, igniting another emotional entanglement. Cindy eventually helps Jolene escape from the hospital, hiding her in her apartment. Using the money she earns from her portraits, Jolene boards a bus westward out of South Carolina, then hitchhikes further across the country, supporting herself through prostitution as she moves toward new destinies.
Her journey carries her to Arizona, where she works as a waitress at an outdoor diner and meets Coco Leger [Rupert Friend], an aspiring musician and tattoo artist. A romance blooms, Jolene moves in with Coco, and he convinces her to marry. However, Coco’s life is tangled in cocaine addiction and drug dealing to sustain his habit and the parlor. One night, a young woman arrives claiming to be Coco’s wife—Marin [Denise Richards]—and presenting their son, Coco Jr. When Coco returns, Jolene is confronted by both women and then flees, destroying the parlor, dumping the drug money on the table, and placing her ring in the center of the cocaine before dialing 911 and escaping.
In Las Vegas, Jolene becomes an erotic dancer and encounters Sal Fontaine [Chazz Palminteri], a mobster who showers her with luxury and treats her as a centerpiece of a glamorous lifestyle. He invites her to abandon dancing and move into his high-rise condo, where she enjoys a life of upscale dinners and artistic expression. But one night, Sal asks her to come downstairs and wait for him; she falls asleep, only to discover Sal dead and the mob closing in on her. Jolene escapes and hitchhikes to Tulsa.
In Tulsa, Jolene finds work as a receptionist and banquet server, where she meets Brad Benton [Michael Vartan], a wealthy, outwardly religious, and arrogantly entitled young man who relentlessly pursues her. He pressures Jolene to marry quickly. On their wedding night, he discovers a tattoo on her body and violently rapes her. When Jolene becomes pregnant, he interrogates her about her sexual history; when she resists answering, he slaps her. After their baby is born, Brad’s parents probe Jolene’s past and inform him, triggering a brutal retaliation where he attacks Jolene and permanently damages her vocal cords. Despite Jolene’s efforts to leave with Brad Jr., a domestic-violence lawyer refuses to take her case because of her past. A child custody battle ensues, and Jolene is arrested for kidnapping, with Brad granted an annulment. She is convicted of the kidnapping and given supervised visits, finally choosing to step away from her infant, believing he can imagine his mother as anyone.
The story moves to Los Angeles, where Jolene becomes a comic illustrator for a graphic novel company, weaving the events of her life into her artwork. In her final narration, she reveals a dream of becoming an actress and hints that a film studio might someday want to use her story. She even imagines herself returning to Tulsa in a limousine to visit her son, a vision that underscores her enduring hope and resilience as she walks off, leaving the frame behind.
