Trivia / The Holdovers

• Acting for Two: Alexander Cook plays both a priest and a bartender.
• Actor-Inspired Element:
  • Hunham's lazy eye was Paul Giamatti's idea.
  • Dominic Sessa suggested Angus doing a cartwheel while running.
  • Da'Vine Joy Randolph wore her grandmother's glasses in the film.
• Actor-Shared Background:
  • Paul Giamatti grew up in a similarly privileged position as Paul Hunham (being the son of A. Bartlett Giamatti, former Yale president and eventual baseball commissioner), and himself attended a boarding school much like Barton Academy.
  • Dominic Sessa was also a high school senior at a boarding school when he was cast as Angus Tully.
• Cast the Expert: Joe Howell plays the liquor store clerk who says "here you go, killer" as he gives the package to Hunham. He owned the store the scene was filmed in.
• The Danza: Paul Giamatti plays Paul Hunham.
• Darkhorse Casting: Dominic Sessa, who had never acted on camera before this film, was attending one of the schools being used as the location for Barton when he auditioned for the role of Angus. Paul Giamatti even had to lobby for him after Alexander Payne was concerned about his lack of on-camera experience.
• Dyeing for Your Art:
  • Hunham has a lazy eye, while Paul Giamatti does not, so to achieve this he wore one contact lens that made it difficult for him to see.
  • Da'Vine Joy Randolph decided to smoke real cigarettes, since she felt the fake ones looked unrealistic.
• Irony as She Is Cast: Dominic Sessa plays a character who falls while ice skating. He had been a hockey player and found it difficult to fall on command.
• Star-Making Role:
  • For Davine Joy Randolph, who was most recognizable to audiences for supporting roles in Dolemite Is My Name and Only Murders in the Building before winning a whole host of awards (including an Oscar) for her role as Mary.
  • Also for Dominic Sessa, who hadn't been in any screen role before this but wowed critics, who praised him for going toe-to-toe with the seasoned Giamatti.
• Underage Casting: Hunham is meant to be older than the school principal, as he's said to have been a former student of his. There is only two years between Paul Giamatti and Andrew Garman.
• What Could Have Been:
  • The first concept was for a television pilot called Stonehaven and set in the modern day. Alexander Payne suggested a period piece in either 1958 or 1970, and they went with the latter to avoid seeming too similar to Dead Poets Society.
  • They also considered shooting on film to properly make it look like a 1970s film, but digital was decided to be more practical.
  • Angus was written to be a 15-year-old freshman, but Dominic Sessa convinced Alexander Payne to make him a junior instead, feeling at 18 he looked too old to play 15.
• Write What You Know: Screenwriter David Hemingson based some of the events of the film on his own life. The scene with the prostitute is inspired by an incident that happened to him and his uncle while the cherries jubilee scene happened to him and his mother.