- Award Snub: As divisive as the film was, Cameron Diaz earned critical acclaim for her performance, and it seemed like she was a contender for an Oscar nomination (as she had been recognized by the Golden Globes, BFCA, SAG, and a number of critics groups). Unfortunately, she just missed out.
- Awesome Music: The ending is set to an early version of Sigur Ros's "Untitled 4/Njósnavélin". It also features Radiohead, Paul McCartney, this special Leitmotif by Nancy Wilson, and Jeff Buckley's Lyrical Dissonance "Last Goodbye" fits perfectly for the part in which it's being played.
- Broken Base: Which one is better? Vanilla Sky or Open Your Eyes? One of the few cases where the "Foreign Original Vs. Hollywood Remake" debate is pretty legitimate, with solid arguments on both sides.
- Critical Dissonance: Critical reaction was decidedly mixed, but it made over 100 million at the box office and is Crowe's second most successful film.
- Follow the Leader: Eternal Sunshine of the Spotless Mind, Inception, Sucker Punch, and an army of less successful wannabes all borrow pretty heavily from concepts in Vanilla Sky, but it's rarely acknowledged. Inception's Mal is almost beat-for-beat Julianna (the former lover who killed herself because of the lead and is now a malicious and insidious force wrecking the dream world), while Eternal Sunshine is likewise a Genre-Busting blend of romance, science fiction and psychological thriller, the relationship between Joel and Clem following many of the same emotional beats as that of Sophia and David.
- Harsher in Hindsight: As with many films set in New York before 9/11, it depicts the Twin Towers standing. The end of the film has David hurling himself off the top of a New York skyscraper, which took on a darker resonance after many people in the Twin Towers did the same thing.
- Mood Dissonance: The "Narm" line below may be funny for viewers. On the other hand, the fact that it's coming out of a clearly unstable woman recklessly driving a speeding car with David in the passenger seat may also produce some other feelings.
- Narm: "I swallowed your cum, it means something!"
- Nightmare Fuel: David's flashing from healthy face to freakish face when his dream is breaking up. Shudder.
- One-Scene Wonder: Tilda Swinton shows up near the end of the film to deliver a sales pitch for Life Extension.
- Rewatch Bonus: Stacks and stacks of Foreshadowing, among other things. Roger Ebert even went so far as to admonish prospective viewers not to try to analyse the film until after they'd seen it twice.
- Sci Fi Ghetto: Is it a romance involving dreams? Is it Sci-Fi?
- Unintentionally Sympathetic: While the film is ambiguous about how much sympathy Julianna deserves, the fact that she genuinely loves David to the point of killing herself earned her a lot of sympathy from the audience, as well as the fact some people thought that Sofia isn't really particularly interesting. This couples with the fact that Julianna isn't really an obsessive stalker like her original counterpart Nuria (all of the stalker-ish actions is done by her dream form), and she is portrayed by Cameron Diaz, who has much more acting experience than Nuria's actress Najwa Nimri and Sofia's actress Penelope Cruz as well as arguably outshines Cruz, and you might have a clear picture why Julianna ended up being the one the audience root for.
- The Woobie: David after his car crash, with shades of Jerkass Woobie (particularly in the nightclub scene).
YMMV / Vanilla Sky