Liev Schreiber's theatrical film debut. His first credited role was in Janek: The Silent Betrayal (1994), which premiered on television the day before this movie opened in theaters.
Director Nora Ephron is the voice of the Los Angeles Times' automated phone responder in the film.
When Dr. Kinsky (Rob Reiner) is complaining about Vanessa (Michele Singer) to Philip (Steve Martin), he mentions that she has twelve pillows, in all sorts of shapes, and at night, before they go to bed, they have to take all twelve pillows, and then in the morning they have to replace all the pillows, for no real purpose. This is the same routine that Ben Stiller and Jennifer Aniston go through in Along Came Polly (2004).
All of the characters reflect Christmas icons: Felix (Anthony LaPaglia) is Santa Claus, Gracie (Juliette Lewis) the Virgin Mary, Philip (Steve Martin) is an elf, Catherine (Rita Wilson) an angel, Mrs. Muchnick (Madeline Kahn) is the Grinch, Mr. Lobel (Robert Klein) is Scrooge, Louie (Adam Sandler) is the Little Drummer Boy, Chris (Liev Schreiber) is Rudolph, and Stanley (Garry Shandling) the Christmas tree.
Mrs. Munchnik (Madeline Kahn) reads an issue of "Distress Magazine". In Santa Claus Is a Stinker (1982), the suicide prevention hotline was called "SOS Distress".
The cast includes several actors who appeared as guests or played roles on The Larry Sanders Show (1992): Jon Stewart, Adam Sandler, Steven Wright, Haley Joel Osment, Rob Reiner, and Garry Shandling.
The first and only (as of April 2020) time that Steve Martin and Rob Reiner have worked on a film together. They share some screen time together approximately halfway through the film. Although the two never previously or subsequently worked on any other films together, Martin, in fact was a frequent collaborator on several films directed by Rob's father, Carl Reiner. Carl Reiner and Steve Martin worked together on The Jerk (1979), Dead Men Don't Wear Plaid (1982), The Man with Two Brains (1983) and All of Me (1984) all of which were directed by Carl Reiner and featured Martin as the lead actor.
Madeline Kahn (Mrs. Munchnik) & Anthony LaPaglia (Felix) also worked together on Betsy's Wedding (1990) as Lola Hopper & Stevie Dee respectively.
Kadeem Hardison and Rosie Perez were originally considered to play Felix and Gracie.