Cameron Crowe and Tom Cruise both tried to persuade legendary director Billy Wilder to make an appearance in the film, but he declined.
Kurt Russell agreed to do the film without reading the script.
The title Vanilla Sky was considered for Cameron Crowe's previous movie, Almost Famous (2000). The original title for Almost Famous was actually "Untitled", however Dreamworks would not allow this, so Cameron Crowe titled the bootleg edition of Almost Famous on DVD "Untitled".
The scene with Tom Cruise alone in Times Square is not computer enhanced. The production was given unprecedented permission to shut down Times Square for one Sunday. At the time, the news ticker was providing updates on the Bush-Gore election. To avoid dating the film, Crowe got permission to change the NASDAQ sign in post-production.
Penelope Cruz also starred in Abre los ojos (1997), of which this film is a remake.
To Kill a Mockingbird (1962) is one of director Cameron Crowe's all time favorite films and is prominently featured in Vanilla Sky. Also, at the beginning of Almost Famous, Crowe's previous work, William Miller and his mother are having a discussion about Atticus Finch, the protagonist of To Kill a Mocking Bird.
Cameron Crowe says that there are 428 references to pop culture made in the film - 429 if you include one made in error.
Early in the film, David's car's inspection sticker reads "2/30/01".
The sticker on David's car reads 2/30/01, a fictional date. On the commentary, Cameron Crowe says that it was an accident, although it lead to one of the different interpretations of the story.
Studio executives wanted Cameron Crowe to use special effects to remove shots of the World Trade Center after the terrorist attacks of 11 September 2001. Crowe didn't remove them, and they appear in several shots of New York.
The photo on the magazine cover that the editor keeps asking David's opinion on, (white letters or yellow letters) is of Izabella Miko, taken from the "Girls of Coyote Ugly" issue of Maxim.
Cameo: [Steven Spielberg] A guest at David's birthday party (wearing a Pre-Crime cap from Minority Report (2002). (Spielberg and Cruise were preparing to begin filming "Minority Report" at that time)
The song "I Fall Apart" on the soundtrack is credited to 'Julianna Gianni' - the name of Cameron Diaz's character - and is actually performed by Cameron Diaz.
In Tom Cruise's bedroom, there is a poster for _Jules et Jim (1961)_ , a French movie in which the climactic scene involves the female star driving a car with her and her lover off a bridge.
During David's birthday party, someone comments on a guitar in a glass case. They state "Danny Bramson gave it to him for his birthday last year". Danny Bramson is the music supervisor for this film.
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