From a prison cell where he has been charged with murder, David Aames (Tom Cruise), in a prosthetic mask, tells his life story to court psychologist, Dr. Curtis McCabe (Kurt Russell).
In flashback, David is shown to be the wealthy owner of a large publishing firm in New York City which he inherited from his father, leaving its regular duties to his father's trusted associates. As David enjoys the bachelor lifestyle, he is introduced to Sofia Serrano (Penélope Cruz) by his best friend, author Brian Shelby (Jason Lee) at a party. David and Sofia spend a night together talking and fall in love. When David's former lover, Julianna "Julie" Gianni (Cameron Diaz), hears of Sofia, she attempts to kill herself and David in a car crash. Julie dies but David survives, his face grotesquely disfigured, leading him to wear a mask to hide the injuries. With no hope of repairing the damage through plastic surgery, David cannot come to grips with the idea of wearing the mask for the rest of his life. On a night out with Sofia and Brian, David gets hopelessly drunk and Sofia and Brian leave him to wallow in the street outside.
David is awakened the next day in the street by Sofia, who apologises for deserting him the night before, and takes him home. The two continue to see each other, and David has his face surgically repaired despite being told it was impossible before. Though his life seems perfectly content, David finds oddities, such as brief visions of his distorted face, and a man (Noah Taylor) at a bar that tells him David could control the world and everyone in it, if he wanted to. One day, when he goes to Sofia's apartment, he finds Julie there instead; all of the previous mementos of Sofia now show Julie's face. Angry and confused, David suffocates Julie, and is later arrested and placed in a mental institution, finding his face has reverted to its previously disfigured state.
David completes telling his story to Curtis, who proceeds to then visit David further for more sessions to try to help him recuperate. During one interview Curtis tells David the staff reported him calling out "Ellie" in a bad dream and asks who she is. David later sees a nearby TV advertisement for "Life Extension", a company that specializes in cryonic suspension, and realises he'd actually called out the letters "L" and "E". Under Curtis' and a police officer's guard, David is taken to the Life Extension offices, where salesclerk Rebecca (Tilda Swinton) explains they freeze people just after the point of death until a cure for their ailment is available in the future, keeping their brain active by placing them in a lucid dream state. David becomes anxious and breaks free of Curtis, realizing he is in his own lucid dream that has gone wrong, and calls for tech support.
David finds himself in the empty lobby of the offices, and the man whom he saw earlier at the bar appears, claiming to be David's tech support from Life Extension, which is now known as the Oasis Project. They ride up in an elevator to the top of an impossibly tall building, the height triggering David's severe acrophobia. The man explains that David has been in cryonic sleep for 150 years. David had opted for Life Extension's services after struggling with his breakup with Sofia and his disfigurement, and after securing the publishing company to its associates, proceeded to kill himself with a drug overdose; Life Extension preserved his body and, as David directed, put him into his lucid dream starting from the drunken night when Sofia left him, under the "vanilla sky" from a Monet painting. However, during his sleep, the dream went horribly wrong and attempted to incorporate elements from his subconscious, such as substituting Julie for Sofia and creating a father-figure in Curtis. As they arrive at the top of the building, the man offers David a choice: either to be reinserted into the corrected lucid dream, or return to the real world by taking a literal leap of faith off the roof that will wake him from his sleep. David decides to wake up, ignoring the vision of Curtis that his subconscious has brought to life to talk him out of it. David envisions Sofia and Brian to say his goodbyes. Conquering his final fear, David jumps off the building, his life flashing before his eyes, and whites out immediately before hitting the ground. A female voice commands him to "open your eyes" (a recurring theme in the movie), and the film ends with David opening his eyes.
The 2015 Blu-ray release offers the option to watch the film with an alternate ending. This alternate ending expands greatly upon the details at the end of the film. While it all leads to the same conclusion, there are additional scenes, alternate takes, and alternate dialogue.
After Rebecca describes the lucid dream, David rushes out of the room but does not immediately dash towards the elevator. He meets McCabe in the restroom who tries to convince him that this is all a hoax and a con and that his case is going to trial. David tells him that he's only in his imagination. Much like in the theatrical cut, the Beach Boys' "Good Vibrations" plays, but this version makes it clear that David hears the music and that he chose it; meanwhile McCabe tries to convince him there is no music.
At this point, David dashes out of the restroom for the elevator the way he does in the theatrical cut, but the scene in the lobby is expanded – David shoots the police officer who is firing at him and is then surrounded by a SWAT team whom McCabe tries to talk down, but the SWAT team fires at both of them. They black out and wake up in the emptied lobby where McCabe continues to applaud what he believes is a performance while David gets into the elevator with Ventura and tells him what happened at the end of his real life.
Once they reach the roof, McCabe re-enters again and his pleas to David not to believe Ventura become more and more desperate until he collapses onto the ground in despair. David's interaction with Sofia is extended as he tells her he loves her but can't settle for a dream. He then jumps off the building and screams that he wants to wake up as images from his life flash before his eyes. He wakes up in bed and a voice tells him "Open your eyes. You're going to be fine."
After the American debut of Alejandro Amenábar's 1997 Spanish film Abre los ojos (Open Your Eyes) at the 1998 Sundance Film Festival, Tom Cruise and his producing partner Paula Wagner optioned the remake rights. Hoping to entice director Cameron Crowe, who previously collaborated with Cruise on Jerry Maguire, Cruise invited Crowe over to his house to view the film. Cruise has stated:
I've been offered a lot of films to buy and remake, and I never have because I felt it was too connected with the culture of that place, whatever country it was from. But this was a universal story that was still open-ended, that still felt like it needed another chapter to be told.
The title of the film is a reference to depictions of skies in certain paintings by Claude Monet. In addition to Monet's impressionistic artwork, the film's tone was derived from the acoustic ballad "By Way of Sorrow" by Julie Miller and a line from an early interview of Elvis Presley in which he said, "I feel lonely, even in a crowded room."
Principal photography for Vanilla Sky began in late 2000 and concluded in March 2001. On November 12, 2000, shooting for the scene of the deserted Times Square in New York took place in the early hours of the day. A large section of traffic was blocked off around Times Square while the scene was shot. "There was a limit on how long the city would let us lock everything up even on an early Sunday morning when much of NYC would be slow getting up," said Steadicam operator, Larry McConkey. "Several times we rehearsed with Steadicam and Crane including a mockup of an unmovable guardrail that we had to work the crane arm around. [Cruise] participated in these rehearsals as well so we shared a clear understanding of what my limitations and requirements would be."
Filming lasted for six weeks around the New York City-area, which included scenes shot in Central Park, Upper West Side, SoHo, and Brooklyn. One prominent location in the area was the Condé Nast Building that served as Aames Publishing and David’s office. After filming finished in New York, production moved to Los Angeles, where the remainder of interior shots were completed at Paramount Studios. Crowe intentionally left in shots of the World Trade Center after the September 11 attacks in 2001 as a tribute.
Despite the film's distorted aspects of reality, the style of cinematography remains grounded for much of the film. "I didn't do anything that was overtly obvious, because the story revolves around the main character not knowing whether he's in a state of reality, a dream or a nightmare, so we want it to feel a little ambiguous," said cinematographer, John Toll. "We want the audience to make discoveries as [Cruise]'s character does, rather than ahead of him." American Cinematographer magazine wrote a feature story on the lighting designer Lee Rose's work on the film.
Aside from selected works by Icelandic group Sigur Rós, the musical score for Vanilla Sky was composed by Crowe's then wife, Nancy Wilson, who previously scored Almost Famous. Wilson spent nine months working on the film's music, which was done through experimentation of sound collages. "We were trying to balance out the heaviness of the story with sugary pop-culture music," said Wilson. "We made sound collages of all kinds. We were channeling Brian Wilson to a large extent. I was recording things through hoses, around corners, playing guitars with cello bows, and with [music editor] Carl Kaller, we tried all kinds of wacky stuff. In the murder–sex scene sound collage, Cameron even used Brian Wilson’s speaking voice from a Pet Sounds mix session."
According to Cameron Crowe's commentary, there are five different interpretations of the ending:"Tech support" is telling the truth: 150 years have passed since Aames killed himself and subsequent events form a lucid dream.
The entire film is a dream, evidenced by the sticker on Aames' car that reads "2/30/01" (February 30 does not occur in the Gregorian calendar).
The events following the crash form a dream that occurs while Aames is in a coma.
The entire film is the plot of the book that Brian is writing.
The entire film after the crash is a hallucination caused by the drugs that were administered during Aames' reconstructive surgery.
Crowe has noted that the presence of "Vanilla Sky" marks the first lucid dream scene (the morning reunion after the club scene)—all that follows is a dream.
Vanilla Sky opened at #1 at the box office in the United States when it was first presented on December 14, 2001. The opening weekend took in a gross income of $25,015,518 (24.9%). The final domestic gross income was $100.61 million while the foreign gross income was slightly higher at $102.76m for a worldwide gross income of $203,388,341.
Vanilla Sky holds an approval rating of 42% on Rotten Tomatoes based on 166 reviews. Metacritic reported, based on 33 reviews, a "Mixed" rating of 45 out of 100.
Roger Ebert's printed review of Vanilla Sky awarded the film three out of four stars:
Think it all the way through, and Cameron Crowe's Vanilla Sky is a scrupulously moral picture. It tells the story of a man who has just about everything, thinks he can have it all, is given a means to have whatever he wants, and loses it because—well, maybe because he has a conscience. Or maybe not. Maybe just because life sucks. Or maybe he only thinks it does. This is the kind of movie you don't want to analyze until you've seen it two times.
Ebert interpreted the ending as an explanation for "the mechanism of our confusion", rather than a device that tells "us for sure what actually happened."
Film critic Richard Roeper identified the film as the second best of 2001.
A more mixed review from The New York Times early on calls Vanilla Sky a "highly entertaining, erotic science-fiction thriller that takes Mr. Crowe into Steven Spielberg territory", but then it notes:
As it leaves behind the real world and begins exploring life as a waking dream (this year's most popular theme in Hollywood movies with lofty ideas), Vanilla Sky loosens its emotional grip and becomes a disorganised and abstract if still-intriguing meditation on parallel themes. One is the quest for eternal life and eternal youth; another is guilt and the ungovernable power of the unconscious mind to undermine science's utopian discoveries. David's redemption ultimately consists of his coming to grips with his own mortality, but that redemption lacks conviction.
A negative review was published by Salon.com, which called Vanilla Sky an "aggressively plotted puzzle picture, which clutches many allegedly deep themes to its heaving bosom without uncovering even an onion-skin layer of insight into any of them." The review rhetorically asks:
Who would have thought that Cameron Crowe had a movie as bad as Vanilla Sky in him? It's a punishing picture, a betrayal of everything that Crowe has proved he knows how to do right....But the disheartening truth is that we can see Crowe taking all the right steps, the most Crowe-like steps, as he mounts a spectacle that overshoots boldness and ambition and idiosyncrasy and heads right for arrogance and pretension—and those last two are traits I never would have thought we'd have to ascribe to Crowe.
Peter Bradshaw of The Guardian and Gareth Von Kallenbach of the publication Film Threat compared Vanilla Sky unfavorably to Open Your Eyes. Bradshaw says Open Your Eyes is "certainly more distinctive than" Vanilla Sky, which he describes as an "extraordinarily narcissistic high-concept vanity project for producer-star Tom Cruise." Other reviewers extrapolate from the knowledge that Cruise had bought the rights to do a version of Amenábar's film. A Village Voice reviewer characterized Vanilla Sky as "hauntingly frank about being a manifestation of its star's cosmic narcissism".
Cameron Diaz's performance was critically acclaimed, with the Los Angeles Times' film critic calling her "compelling as the embodiment of crazed sensuality" and The New York Times reviewer saying she gives a "ferociously emotional" performance. Edward Guthmann of the San Francisco Chronicle similarly says of the film, "most impressive is Cameron Diaz, whose fatal-attraction stalker is both heartbreaking and terrifying." For her performance, Diaz won multiple critic's group awards, as well as earning nominations for the Golden Globe Award, Screen Actors Guild Award, Critics' Choice Movie Award, Saturn Award, and AFI Award. Penélope Cruz's performance, however, earned her a Razzie Award nomination for Worst Actress (in addition to her roles in Blow and Captain Corelli's Mandolin).