The food that Miles, Jack, and Miles' mother consume during the dinner at Miles' mother's house gave the three actors food poisoning.
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Paul Giamatti admitted to faking every bit of wine knowledge, and not understanding why anybody would care about it. He also claims he was shocked that he was cast in a lead role and initially thought it was a practical joke.
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During his audition, Thomas Haden Church stripped naked because that was what the scene called for. He later learned that he was the only actor to do that.
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During an emotional scene in the film, Miles talks with great passion about Pinot Noir. After the release of this movie, sales of Pinot Noir wines rose by more than 20 percent over the 2004-05 Christmas/New Year period, compared to the same period the previous year. A similar phenomenon was experienced in British wine outlets. Miles is deeply disparaging, in a different scene, about Merlot, and sales dropped after the film came out. Ironically, Miles's prized bottle of wine, a 1961 Château Cheval Blanc, is a blend of Merlot and Cabernet Franc, another grape Miles disparaged.
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An entire street was blocked off by the police for the filming of the scene in which M.C. Gainey runs naked down the street. Moreover, the people who lived in houses on said street were paid by the crew to stay inside their homes during the shooting of this particular scene.
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Alexander Payne was flying back from Edinburgh, where he had been at a film festival promoting Election (1999), when he finally had a chance to read Rex Pickett's book Sideways. As soon as he landed, Payne ran to a pay phone to call his agent about purchasing the rights. He later told Pickett he liked his novel because his characters were "so f*cking pathetic."
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George Clooney campaigned for the part of Jack, but Alexander Payne thought Clooney was too big a star. However, Clooney got to play the lead in Payne's next full feature, The Descendants (2011).
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Sandra Oh learned how to ride a motorcycle for her part in this film.
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Thomas Haden Church had left film acting, concentrating on voiceover work, when he received a phone call from Alexander Payne to audition for the role of Jack. Church was a finalist for a role in About Schmidt (2002), another Payne film, and Payne wanted to use the actor in one of his films. Funnily enough, his character in the movie is also an actor who has retired from live-action performances to do voice-over work.
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The picture that Miles (Paul Giamatti) looks at when at his mother's home is actually a picture of Paul Giamatti and his father (former Yale University president and Commissioner of Major League Baseball) Bart Giamatti.
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The source novel by Rex Pickett remained unpublished until Alexander Payne bought the film rights. The novel was released a month before the film premiered.
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Most of the dialog in the dinner scene with Miles, Jack, Maya and Stephanie was improvised.
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The first film to win best screenplay from all five "major" critic groups (National Board of Review, New York, Los Angeles, Broadcast Film Critics and National Society of Film Critics), the Golden Globes, the BAFTAs, the WGA and, ultimately, the Academy Awards.
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Most of the wine used in the wine-tasting scenes was non-alcoholic. The actors wound up drinking so much of it that it made them nauseated (and had to periodically switch to the real thing to clean out their palates). Thomas Haden Church estimated that grape juice or non-alcoholic wine was what they consumed 95 percent of the time. Conversely, Paul Giamatti claimed the actors drank real wine, and that he was actually very drunk after shooting a dinner scene.
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Rex Pickett later produced a sequel in novel form named "Vertical", in which Miles writes a best seller and is again reunited with his mother and Jack. However according to Pickett, Alexander Payne had no interest in directing a film version of the sequel.
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When Miles and Jack are sitting beside sea and Jack commiserates over the rejection of Miles' novel, Miles says "I'm a smudge of excrement on a tissue surging out to sea with a million tons of raw sewage," and Jack praises the phrasing, saying he (Jack) could never write anything like that. Miles then informs him that he couldn't write that either, and says he thinks it was a quote from Bukowski, referencing Charles Bukowski. While the quote sounds like something Bukowski could have written, in fact it was written by the Sideways novel's author Rex Pickett, and was never uttered by Bukowski.
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The house where Miles retrieved Jack's wallet was being used as a meth lab up until a few weeks before filming, when it was busted by police. Its interior was left essentially as is because the location scouts thought it was perfect for the scene.
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Alexander Payne and Jim Taylor wrote Maya's speech based off of a passage from Rex Pickett's book, and based some of it on how the director himself feels about wine. However, he didn't think the speech deserved as much praise as it received.
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Thomas Haden Church was nervous about filming the love scene with Sandra Oh, as she was married to Alexander Payne at the time. Initially Church and Oh played the scene as if it was funny, before Payne made the two act more and more passionate with each successive take. Payne and Oh divorced two years later.
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The reason for the film's title is never explained in the film itself, but it is made quite clear in the novel on which the film is based, as the two main characters use the term "sideways" to mean "intoxicated."
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According to W. Blake Gray of the San Francisco Chronicle, the producers had originally wanted to use a bottle of Petrus as the treasured wine gathering dust in Miles' apartment. But Christian Moueix, the chateau's owner, read the script and decided to pass. So, instead it was a bottle of 1961 Cheval Blanc.
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A slapstick scene involving Miles hitting a dog with his car while driving around was cut because it didn't fit the overall mood of the movie.
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The Erganian house is located directly opposite O.J. Simpson's famous N. Rockingham home at the time of the murder of his ex-wife and Ron Goldman.
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A reporter asked Alexander Payne if Miles running down the grassy hill was purposely evoking the opening credits to Little House on the Prairie (1974). It was actually borrowed, with permission, from the thesis film of one of Payne's former classmates.
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Voted movie of the year by Empire magazine in 2005.
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Director Chris Columbus said the film was "a 70s movie made in contemporary times".
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Alexander Payne selected the film's wine list himself.
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Restaurant locations used in the Santa Ynez valley: Solvang Restaurant (breakfast scene before wine tasting); Los Olivos Cafe (dinner scene with Maya and Stephanie); AJ Spurs (dinner scene with Cammie); and of course The Hitching Post.
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When Jack is watching a spring break event on TV, the hairstyles and blindingly-neon swimwear is clearly early-90's. The filmmakers had asked MTV for usage of more current footage from their spring break videos, but the channel was only willing to give them dated material free-of-charge.
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Author Rex Pickett was unhappy with the changes that Sandra Oh (who was married to director Alexander Payne at the time) made to her character: this included changing her name from Terra to Stephanie; having her ride a motorcycle; and giving her a biracial child. In retaliation, in Pickett's follow-up novel, "Vertical", Terra is mentioned as now working as a prostitute in Reno.
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The scenes in the winery "Frass Canyon" were filmed at Fess Parker, a winery owned by former actor Fess Parker, most famous for Disney's series Davy Crockett: King of the Wild Frontier (1955).
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The book that Miles is reading aloud from in the classroom is "A Separate Peace" by John Knowles.
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The guys visit "Frass Canyon" vineyards, which Miles describes with a sneer. "Frass" is insect excrement.
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There was a scene in the film in which Miles throws the hotel Bible in the garbage after looking through the drawer, but it was cut.
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Some of the scenes in the novel were cut from the film version including the boar hunt, the trip to Hearst Castle, and the hot tub scene. Some of the characters and other plot points were also changed.
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Despite receiving Best Actor nominations at the Golden Globes, Screen Actors Guild, and four of the five "major" critic groups (Broadcast Film Critics, National Society of Film Critics, Los Angeles, and winning at New York), Paul Giamatti failed to receive an Oscar nomination. Conversely, Clint Eastwood was nominated for Best Actor at the Academy Awards for Million Dollar Baby (2004) despite not being recognized at any of the major precursor awards for his performance, aside from the National Society of Film Critics.
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Thomas Haden Church's character is a former TV star now doing commercial voiceovers. This mirrors his own career.
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Despite the film being an adaption of the novel, Alexander Payne cited Il Sorpasso (1962) as a big inspiration for Sideways and the way he shot it. While making Sideways, Payne looked at the film shot-by-shot and he notes that each shot in the film has "a beginning, a middle, and an end." "Il Sorpasso" showcases the humanity of Italy, according to Payne, and while watching the film "you really get to see Italy in 1962."
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"The Sideways Wine Club", the licensee of Fox Searchlight Pictures, was started in April of 2005 and became the fastest growing wine club in the United States. It originally featured many of the wines seen in the movie then expanded to include similar wines from all over the world - wine from boutique producers who pour their heart and soul and second mortgage into their venture.
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The only Best Picture Oscar nominee that year not to be nominated for Best Actor, or in either of the lead acting categories.
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The two lead actors of this movie (Paul Giamatti and Thomas Haden Church) would both later voice exterminators in computer animated films released in the summer of 2006; Giamatti in The Ant Bully (2006) and Church in Over the Hedge (2006). And they would also both later play Spider-Man villains; Giamatti plays Rhino in The Amazing Spider-Man 2 (2014) and Church plays Sandman in Spider-Man 3 (2007).
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During the opening credits, Miles drives west along Sunset Boulevard crossing the 405 freeway, indicating that the Erganians' house is located in the posh L.A. neighborhood of either Brentwood or Pacific Palisades.
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Miles' (Paul Giamatti) prized bottle of wine, a 1961 Château Cheval Blanc, is the same wine that Mel (Jane Adams) offers to Niles (David Hyde Pierce) as a gift in Frasier (1993).
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A scene where Miles runs over a dog was cut, even though Paul Giamatti's facial expressions in the scene made it supposedly funnier than it sounded. Scenes where an agitated Jack calls his fiancée during his trip were also taken out.
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Included among the "1001 Movies You Must See Before You Die", edited by Steven Schneider.
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Both of the New York Times crossword puzzles that Miles solves in the movie are actual published puzzles. The constructor's byline on the second puzzle Miles solves is visible; the puzzle was constructed by Alan Arbesfeld, and was published in the Times on 9 October 2003. The constructor's byline on the first puzzle (the one Miles solves while driving) is not visible; this puzzle was constructed by Craig Kasper and was published in the Times on 27 September 2003.
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Costumes are handled by Wendy Chuck. Paul Giamatti's character in Billlions is called Chuck and his wife is Wendy.
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Alexander Payne changed the ending of the book, because he thought it was "too Hollywood". In the book, Maya showed up at Jack's wedding to say she sees Miles in a more positive light after reading his manuscript.
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When Stephanie is assaulting Jack with her motorcycle helmet, she is wearing a t-shirt with a peace symbol on the front.
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