Filmmaker Leonard "Leo" Fife, portrayed by Richard Gere, is facing the final stages of his battle with cancer. Revered as a hero by the progressive community in Canada, Leo is best known for his impactful muckraking documentaries that have captivated audiences and sparked conversation about important social issues. His life story is rich with intrigue and complexity, including the legend that he fled from the United States to Montreal to avoid the Vietnam War draft. Subsequently, he embarked on a Kerouac-inspired road trip to Castro's communist Cuba.
As he nears the end of his life, Leo consents to participate in a documentary being produced by his former students, Malcolm and Diana, played by Michael Imperioli and Victoria Hill, respectively. Malcolm assures Leo that the film aims to honor his career and legacy. However, aware of his own morally ambiguous past, Leo sees this documentary as a chance for personal redemption, particularly in the eyes of his wife Emma, who is also a former student of his, portrayed by Uma Thurman. Throughout his life, Leo has repeatedly misled the public and left a trail of abandoned relationships, making this confession all the more significant.
Years before his diagnosis, Leo, an aspiring novelist, resides in Virginia with his pregnant wife Alicia, played by Kristine Froseth, and their son Cornel, portrayed by Zach Shaffer. Despite his potential stability, Leo feels constrained by the conventional lifestyle and affluent in-laws that surround him. Yearning for a change, he accepts a teaching position at Goddard College in Vermont, while keeping this news a secret from Alicia, who values their life in Virginia. In an attempt to sway Leo to remain, his father-in-law even offers to guide him into the family business, which adds to Leo's turmoil as he wrestles with his decisions.
As the documentary unfolds, the narrative reveals Leo's abandonment of his family when he made the decision to escape to Canada. The adult Cornel, in a poignant voiceover presumably meant for the documentary, reflects on not having seen his father for thirty years. In a bid to shield Leo's image, Emma intervenes, expressing deep concerns over Leo's mental state due to his illness and reliance on prescription medication. Despite her worries, both Leo and Malcolm agree to continue the interview, leading to a confrontation with Leo's troubling history.
Throughout the film, Leo reveals various moments from his past that paint a picture of both his flaws and vulnerabilities—he recalls stealing from a family friend who had provided him with work after dropping out of college, seducing both Diana and Emma while in a position of authority, and even infidelity towards his first wife during her pregnancy. As Emma shares a painful memory of how her son Cornel approached Leo at a film festival, she reflects on how he brusquely informed Cornel that he had "no son," reinforcing the deep scars left by his choices.
Leo revisits critical events leading up to his flight to Canada, meeting with his old friend Stanley, played by Jake Weary, who reveals that life hasn't turned out as he hoped. The narrative intensifies when Leo receives devastating news of Alicia's miscarriage, yet finds himself entangled in an unexpected romantic advance from Stanley's wife, Gloria, further complicating his moral landscape.
As the interview unfolds, Emma eventually halts the proceedings as Leo's health declines. In a powerful moment captured on a hidden camera, Leo's last words ring out: "> Oh, Canada," echoing both a physical and emotional departure from the life he has known.
Finally, the audience learns of Leo’s true motivations for leaving America rather than the legend he has cultivated over the years—highlighting a complex interplay of self-identity and the search for authenticity. As he reflects on his journey, Leo recalls the moment he crossed the Canadian border, recalling his younger self raising his arms to the sun, stepping toward a new chapter in his life.
