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1* AlternativeCharacterInterpretation: More of the entire film interpretation that Cameron Crowe presents in the audio commentary for the film, which is the film is not really happening as it's seen and that it's a novel written by Brian Shelby, Jason Lee's character, and Brian has David as his lead character as a tribute to the real David Aames who committed suicide.
2* AwardSnub: 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.
3* SugarWiki/AwesomeMusic: The ending is set to an early version of Sigur Ros's "Untitled 4/Njósnavélin". It also features Music/{{Radiohead}}, Music/PaulMcCartney, Music/RollingStones, [[https://www.youtube.com/watch?v=OfV-YzMfvns&feature=related this special]] {{Leitmotif}} by Nancy Wilson, and Music/JeffBuckley's LyricalDissonance "Last Goodbye" fits perfectly for the part in which it's being played.
4* BrokenBase: 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. On the other hand, the debate itself is probably only possible because the remake is so faithful to the original in the first place.
5* CriticalDissonance: Critical reaction was decidedly mixed, but it made over 100 million at the box office and is Crowe's second most successful film.
6* HarsherInHindsight: As with many films set in New York before 9/11, it depicts the Twin Towers standing. The end of the film has David [[spoiler: 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.
7* {{Narm}}: "I swallowed your cum, it means something!"
8* NightmareFuel: David's flashing from healthy face to freakish face [[spoiler: when his dream is breaking up.]] Shudder.
9* OneSceneWonder: Creator/TildaSwinton shows up near the end of the film to deliver a sales pitch for Life Extension.
10* RetroactiveRecognition: Creator/MichaelShannon plays the prison guard.
11* RewatchBonus: Stacks and stacks of {{Foreshadowing}}, among other things. Creator/RogerEbert even went so far as to admonish prospective viewers not to try to analyse the film until after they'd seen it twice.
12* SciFiGhetto: Is it a romance involving dreams? Is it Sci-Fi?
13* UnintentionallySympathetic: 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.
14* TheWoobie: David after his car crash, with shades of JerkassWoobie (particularly in the nightclub scene).

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