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▲A critically acclaimed 2004 comedy/drama. Middle-aged [[Heterosexual Life Partners|BFFs]] Miles (Paul Giamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week, as Miles' gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[Drowning My Sorrows|just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[One Last Fling|wants to get laid one more time]] before settling down with one woman. During the week, they encounter two women: one is Maya (Virginia Madsen), a kindhearted, beautiful, and intelligent woman who Miles has longed after for a while (not in the least because she's just as knowledgeable about wine as he is) but [[Cannot Spit It Out]]. The other is Stephanie (Sandra Oh), a spirited [[MILF]] wine pourer who instantly takes Jack up on his charming advances. [[Hilarity Ensues|Hilarity]], [[Crowning Moment of Heartwarming|heartwarming]], [[Bittersweet Ending|and bittersweetness ensues.]] And wine drinking. Lots of it.
It opened to universal acclaim, winning the Oscar for Best Adapted Screenplay, as well as Golden Globes for Best Picture- Musical/Comedy and Best Screenplay, and the Screen Actors Guild Award for Best Ensemble Cast, which was notable since that ensemble was made up of only four actors instead of the usual [[Loads and Loads of Characters|loads and loads of actors]]. It was also a huge success, being Fox's biggest indie hit ever at the time, scoring $70 million domestically after an initial limited release turned into an eventual wide release. It elevated Paul Giamatti from character actor (as seen in films like ''The Negotiator'' and ''[[The Truman Show]]'') to billed actor in more mainstream films. It put the careers of Thomas Haden Church and Sandra Oh on the map after a career in bit roles; Church nabbed the role as The Sandman in ''[[Spider-Man (film)|Spider-Man 3]]'' based off his performance here and Sandra Oh landed a key role in ''[[Grey's Anatomy]]'' shortly after the film's release. It also resurrected the career of Virginia Madsen, an '80s sex symbol who had been relegated over the years as simply "Michael Madsen's sister".
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Also bizarrely got [[Foreign Remake|a remake by the Japanese.]]
{{tropelist}}
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* [[The Eeyore]]: Miles when drunk or depressed.
* [[Even the Guys Want Him]]: Jack claims to be this.
* [[Everyone Can See It]]: Jack immediately notices the [[Unresolved Sexual Tension
* [[
* [[Executive Meddling]]: In-universe: {{spoiler|A publication house passes on Miles' novel, saying that they liked it but did not know how to market it.}}
* [["Falling in Love" Montage]]: Miles and Maya spend a nice day-and-a-half falling for each other to Rolfe Kent's beautiful jazzy piano score.
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{{reflist}}
[[Category:Academy Award]]
{{Golden Globe Award Best Motion Picture Musical or Comedy}}
[[Category:Film]]▼
[[Category:Films of the 2000s]]
▲[[Category:Sideways]]
[[Category:Independent Films]]
[[Category:Films Based on Novels]]
▲[[Category:Film]]
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