Montgomery 'Monty' Kessler [Brendan Fraser] is a Harvard Government senior who shares a cramped house with his friends: Courtney [Moira Kelly], a creative art student; Everett [Patrick Dempsey], a carefree radio disc jockey with a habit of bending the truth; and Jeff, a neurotic medical student who keeps everyone on their toes. While Monty works on his ambitious senior thesis—a skeptical critique of public assistance—the campus routine is upended by a sudden power outage that ruins his hard drive. He scrambles to print a backup copy, but a misstep on the sidewalk sends him tumbling, breaking his ankle and sending the failed thesis plunging down a grate into the boiler room beneath Widener Library.
There, Monty discovers a homeless man, eerily reminiscent of Walt Whitman, who calmly burns page after page of the thesis. He calls campus security, who arrest the man, yet the crucial document slips beyond reach. In court, the man is identified as Simon Wilder [Joe Pesci], a charismatic wanderer with a sharp mouth and a softer heart than his rough exterior suggests. Although Simon survives the legal blow, he is briefly held in contempt, a fine Monty ends up paying. The peacemaking result is a strange, evolving bargain: for every service Monty provides, Simon will return a page of the lost thesis. This odd pact becomes the seed of an enduring bond.
Monty brings Simon to live at his house, where a weathered van in the backyard becomes Simon’s makeshift home. As the weeks pass, the two men forge an unexpected friendship. Monty confides in Simon about his absent father, and Simon offers a window into a very different life. He helps Monty see that the poor and those living on the margins are fully human, worthy of respect and care. Simon also introduces Monty to his own world—his collection of stones, each one symbolizing a memory from his long life at sea and ashore.
The mood in the house shifts as the roommates respond to this new influence. Courtney grows to value Monty’s broadened perspective, and Everett is delighted to have a steadying influence in the van’s repairs in exchange for wine. Jeff, however, remains wary—especially when a bitterly cold night arrives and Simon is barred from the basement. Monty’s decision to lie about why Simon cannot come inside strains the fragile trust, ending their formal arrangement for the moment.
When Christmas break arrives and everyone leaves town, Monty stays behind to rework his thesis. Simon, in a gesture that reinforces their fragile trust, sends a friend to deliver the rewritten pages but makes it clear he does not want to see Monty in person. Monty discovers that Simon has been living on the street, weakened by years of exposure to asbestos in the U.S. Merchant Marines. Deeply moved, Monty invites Simon back into the house and withdraws the earlier bargain, choosing to support him rather than continue the tenuous exchange.
With Simon living under their roof again, the household dynamics shift. Simon begins to receive disability benefits that help cover the rent as Monty commits to a full rewrite of his thesis. The togetherness of the roommates—Courtney and Everett’s support, Jeff’s reluctant openness—helps keep Simon’s dignity intact even as his health deteriorates. Before long, Simon drafts an obituary for himself, revealing that he once left his wife and child to serve in the Merchant Marines. Monty’s initial anger softens into forgiveness, and the two attend a campus pajama party together, a small celebration of the life they’ve built.
A pivotal moment arrives when Simon gently nudges Monty toward confession and love. Courtney, watching the moment unfold, reciprocates Monty’s feelings, and their relationship becomes a bright thread through the story. To honor Simon, Monty agrees to drive him to visit Frank Wilder, Simon’s son he had once abandoned. The long trip delays Monty’s thesis further, but the act of reconciliation feels essential. The group accompanies him, including Jeff, who has come to recognize Simon’s humanity. Frank, however, refuses to acknowledge his father, a disappointment that stings Simon as he speaks with his granddaughter, Marty [Claudia Haro], who asks about her grandfather’s past. Before leaving, Simon adds another stone to his collection, a quiet gesture of memory and legacy.
Back on the road, Simon’s condition worsens. The roommates stay up through the night, turning pages of Walt Whitman as a living litany of memory and hope. By the time they reach home, Simon dies. At his funeral, Monty reads an obituary written by Simon that frames the roommates as a true family and declares that Monty “will graduate life with honor and without regret.” The moment seals a philosophy that Monty will carry into the rest of his life.
Seeking closure and truth, Monty meets with his stern mentor, Professor Pitkannan [Gore Vidal], to explain the shift in his thesis from a pessimistic to a more hopeful subject. Pitkannan accepts the change but informs Monty he will not graduate with honors because of the lateness of the work. In a final symbolic act, Monty returns the Walt Whitman book to Widener Library, signaling that the memory of Simon and his chosen family will always be part of the scholarly home he leaves behind.
The roommates graduate together, and Monty begins a new personal project: a growing collection of memory stones—each one a tangible reminder of people, moments, and choices that shaped his life. The film closes on a quiet, hopeful note, a celebration of human connection, responsibility, and the courage to see others as real people with their own stories, even when those stories come at a cost to one’s hard-won plans.
