Last Night in Rozzie is a drama film that revolves around Ray Timmons, a successful lawyer in New York City who returns to his hometown of Roslindale, Boston after receiving news that his childhood friend, Mikey, is dying of cancer. Ray reconnects with Mikey and meets his young son, Leo, who he promises to reunite with his father before he dies.
However, as Ray spends more time in Roslindale, he is forced to confront a childhood trauma that has haunted him for years. He was involved in a car accident as a teenager that killed two of his friends, and he has carried the guilt and shame of that incident with him ever since. As he tries to help Mikey and Leo, Ray struggles with his own demons and the trauma from his past.
Throughout the film, Ray navigates through the complicated relationships with his friends and family members, including his ex-girlfriend and his overbearing father, as he tries to make amends and find some closure for himself and others. The movie is a poignant exploration of grief, redemption, and the power of forgiveness.