In northwest Indiana, a boy named Rob spends his afternoons in the humid basement of his grandfather Silas, an 80-year-old former navy midshipman who reads aloud from books about train disasters while Rob draws in notebooks. One day, Rob discovers a book about the French painter Manet in a box of donated library books and is captivated by the bright, flat color and flawless draftsmanship. He notices a tiny woman on a swing hidden in a barmaid painting, a detail Silas says proves the boy's exceptional eye. Rob's mother, June, works for a title company. Her boyfriend Robert, a real estate agent, is verbally aggressive and physically menacing toward June and Rob. To distinguish himself from this man, Rob adopts the nickname "Cricket," after the clicking sound he makes before decisions. Silas counsels Cricket to treat Robert like bad weather: something to prepare for but not internalize.
On the first day of spring, Cricket arrives home to discover Silas has died. For months he withdraws, eating alone in Silas's old wingback chair. Robert reappears, and Cricket avoids him by riding his bike through empty streets. One day, a golden-eyed girl a grade above him named Pia stops Cricket on a bridge and recruits him to write vulgar rhyming phrases in ornate calligraphy on a new play structure. June arranges art lessons with Oana, a quiet Romanian émigré whose sister Madelena also fled dictatorship to settle in their small town. Oana teaches Cricket to draw and paint a still life at life-size scale, and he is stunned by the accuracy he achieves. Pia, who is Madelena's piano student, walks Cricket home and urges him to enter a police-sponsored art contest. She convinces him to submit a painting of a dead weasel that unmistakably resembles Robert. Cricket wins first prize. His mother recognizes Robert's features and covers her mouth.
At 15, Cricket works at the Whistlestop, a train-station café managed by J. J. Roulin and staffed by Jed Shipski, a lanky co-worker whose cop father beats him. At the library, Cricket reads about historical apprenticeships and is alarmed to learn that young artists were typically apprenticed by age 12. He signs up for a Saturday life drawing class at the Chicago Academy of Art and takes the train alone to the city. His instructor, Agnes Winter, teaches him the canon of human proportions, and for the first time he feels his innate skill married to formal instruction.
One night, a girl who claims to be the reincarnation of Albert Camus reveals she is Pia, now going by Olympia, her appearance transformed. Olympia has returned to Indiana after her stepfather's indictment. She sends Cricket annotated volumes of Camus's notebooks and delivers torrential lectures on Degas, Tolstoy, and the need to start an art movement. Cricket's nude drawings are briefly displayed in the public library but removed after the Daughters of the American Revolution, a patriotic women's organization, demands their censorship. On his 16th birthday, Cricket spends the day alone at the river, finding peace in drawing. That night, Olympia crashes her car through a plate glass window after her boyfriend Stuart publicly sings a song calling her "inconsequential." Cricket and June rush to the hospital, where Cricket tells Olympia she can never see Stuart again.
Olympia, whose family fortune has collapsed, transfers to the state university. Jed has joined the Reserve Officers' Training Corps (ROTC). Cricket enrolls with money saved from the Whistlestop. At a group critique, a student named Kyle Heaney is praised for a conceptual Polaroid while a virtuosic figurative painter is savaged for her representational crucifixion canvas. Marcus Carpenter, a mostly retired professor, storms in and thunders a defense of technical skill. Cricket and Jed find their way to Carpenter's farmhouse, where he runs an informal atelier with life drawing, sign painting, and Sunday sessions filled with cooking, instruction, and debate about what constitutes art.
When Iraq invades Kuwait in 1990, Jed's ROTC unit is called up. Olympia organizes a conceptual art show in which Cricket and Jed continuously paint a gallery's walls black and white in alternating cycles. After the ground war, Jed is killed in a car accident in Kuwait when his truck veers into a ditch. Cricket paints Jed's portrait obsessively but brings one version to Jed's family only to find it later discarded in their garage. Roulin hangs the portrait in the Whistlestop, calling Cricket and Jed his two boys. Carpenter dies of a heart attack a year later.
In his late twenties, Cricket lives in Chicago, working as a tiler. At Olympia's urging, he takes an unpaid internship at a sterile gallery where he guards an empty room of small abstract sculptures. Olympia arrives, horrified, and physically runs him out of the building. She reveals she is in a green-card marriage to an Argentine man from her master's program at Brown University. Cricket paints Bilyana, a 40-year-old Bulgarian factory worker, in an enormous canvas that becomes the best thing he has ever made. Olympia opens Barry's, a gallery in a former bagel shop, and shows Cricket's large figure paintings alongside cityscapes by Sun-Yu, a Chinese former doctor who is blind and draws cities from memory. Cricket gets drunk, punches the Argentine for mocking Olympia, and walks home through the frozen city.
Years later, Cricket's mother dies after a fall at work. Cricket has been working as a ship-breaker in Turkey, where he was seriously burned in a boiler explosion. Olympia lures him to Philadelphia with a job, concealing that the employer is Kyle Heaney, now a hugely successful artist who employs 40 people in a factory-like studio. Olympia has stage 3 breast cancer and tells no one except Cricket, who sits with her during chemotherapy. Kyle sees Cricket's ink drawing of Olympia and offers $50,000 for the idea as work-for-hire. Through Kyle's wife Honey Panaglovia, a former doctor who is drinking heavily, Cricket learns that Olympia is having an affair with Kyle. Honey has found love letters and an annotated copy of Camus in Kyle's car. One evening, Honey drops her 12-year-old son Luka at the studio with Cricket, then picks him up and leaves him with her mother. That night, Honey returns to the apartment and shoots Kyle six times with his own gun, then drives to the restaurant where they first met and shoots herself.
In his late fifties, Cricket lives on Phuket, Thailand, producing reproductions of famous paintings for tourists. Olympia arrives, clean from heroin for six years, now working as an art adviser. Cricket shows her his single private painting: six months of layered glazes capturing a tropical sky with an inner glow. She declares it the best thing he has ever done and proposes selling it. He refuses, insisting one painting, gotten right, is enough. That night they make love in the warm sea. In the morning, she tries to persuade him to return to the world, and he refuses. She leaves, unable to commit to his island life.
At 74, Cricket runs an atelier in Paris near Notre Dame, teaching students of all backgrounds to draw from life. A bicycle accident has left him unable to raise either arm above his chest. Roulin has died at 98. One evening, Olympia appears unannounced during model auditions, drops her robe on the platform, and calls Cricket up to pose with her. He has not posed nude in 50 years, but he undresses and joins her. They hold each other and whisper about their bodies, their scars, and the 62 years they have known each other. After class, they walk through a blacked-out Paris and return to the studio, where the students' drawings show them entwined in candlelight, their bodies like vines around trees, telling the story of their long, circling, unresolved love.