The Holdovers

In mid-December 1970, Paul Hunham is a classics teacher at Barton Academy, a New England all-male boarding school that he once attended on scholarship. His students and fellow teachers despise him for his strict grading and stubborn personality. Dr. Woodrup, Barton's headmaster and Hunham's former student, scolds him for costing the academy money by flunking a major donor's son, causing Princeton University to rescind the boy's offer of admission.
When another teacher becomes unavailable for the duty, Hunham is forced to supervise five students left on campus during the Christmas holiday break, including Angus Tully, whose mother has cancelled a family trip to Saint Kitts in order to honeymoon with her new husband. Also staying behind is cafeteria manager Mary Lamb, whose late son Curtis attended Barton and recently died in the Vietnam War after being drafted. Unlike most Barton students, Curtis did not get a student deferment because he could not afford to go to college, and was only able to attend the school because of his mother’s job.
To the students' chagrin, Hunham forces them to study and exercise during the break. After six days, one student's wealthy father arrives by helicopter and agrees to take all five students on the family's ski trip with their parents' permission. Angus, unable to reach his parents for permission, is left alone at Barton with Hunham and Mary.
When Hunham catches Angus trying to book a hotel room, they argue about Hunham's disciplinarian policies. Angus runs through the school halls and defiantly leaps into a pile of gym equipment, dislocating his shoulder. Hunham takes him to the hospital. To protect his teacher from blame, Angus lies to the doctors about the circumstances of his injury.
At a restaurant, Hunham and Angus encounter Lydia Crane, Woodrup's assistant, who is fond of Hunham and invites the pair to her Christmas Eve party. Angus, Hunham, Mary, and Barton's janitor Danny attend Lydia's party. There, Angus is taken with Lydia's niece Elise, but Hunham discovers that Lydia has a boyfriend. As Mary gets drunk and has an emotional breakdown over Curtis's death, Hunham insists on leaving early. As he and Angus argue, the teen says that his father is dead and Mary scolds Hunham for his lack of empathy. Feeling remorseful, Hunham arranges a small Christmas celebration. Mary persuades him to grant Angus's wish for a "field trip" to Boston. After dropping off Mary in Roxbury to spend time with her pregnant sister, Angus and Hunham walk through Boston, ice skate and visit the Museum of Fine Arts.
The two encounter a classmate of Hunham's from Harvard College, who has become a successful academic. Embarrassed, Hunham lies about his career, and Angus plays along. Angus learns that Hunham was expelled from Harvard after a legacy donor's son plagiarized his work and then framed him, causing Hunham to semi-deliberately hit him with a car. Although the incident nearly ruined Hunham's career prospects, his old Barton headmaster took pity on him and offered him an adjunct teaching job.
When Hunham and Angus see the film Little Big Man at the Orpheum Theatre, Angus sneaks away and Hunham catches him entering a taxi. The teen explains that he wants to see his father, and Hunham agrees to accompany him, assuming that they are going to a cemetery. However, Angus's father is alive and confined in a psychiatric hospital.
Following the visit, Angus (who takes medication for depression) expresses his fear that he will grow up to become like his father. Hunham comforts him, affirming that Angus is not the same person as his father. Hunham, Angus, Mary and Danny celebrate New Year's Eve together.
In January 1971, when school resumes, Hunham is summoned to Woodrup's office, to respond to a complaint from Angus's mother and stepfather. They say that Angus is not allowed to see his father and that a snowglobe Angus had given him led to a violent incident at the hospital. Angus's mother and stepfather threaten to withdraw Angus from Barton and send him to a military academy. Hunham defends Angus and blames himself, claiming that the visit was his idea. Woodrup allows Angus to remain at Barton while firing Hunham, who steals expensive cognac from Woodrup's office as he leaves.
Mary, trying to come to terms with Curtis's death, gives Hunham a notebook for the monograph he wants to write. Hunham and Angus share a heartfelt handshake as they say goodbye to each other. In his car, Hunham takes a sip of the cognac, spits it out toward the school, and drives away.