[[quoteright:350:http://static.tvtropes.org/pmwiki/pub/images/sideways.jpg]]

A 2004 comedy/drama. Middle-aged [[HeterosexualLifePartners BFFs]] Miles (Creator/PaulGiamatti) and Jack (Thomas Haden Church) take off to California's wine country for the week as Miles's gift to Jack before he is to be married on Saturday with Miles as best man. Both, however, have a hidden agenda: Miles [[DrowningMySorrows just wants to drink]] as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack [[OneLastFling 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 kind-hearted, 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 CanNotSpitItOut. The other is Stephanie (Sandra Oh), a spirited MILF wine pourer who instantly takes Jack up on his charming advances. [[HilarityEnsues Hilarity]], [[CrowningMomentOfHeartwarming heartwarming]], [[BittersweetEnding 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 [[LoadsAndLoadsOfCharacters 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 ''Film/TheTrumanShow'') 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 ''[[Film/SpiderMan Spider-Man 3]]'' based off his performance here and Sandra Oh landed a key role in ''[[GreysAnatomy 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".

[[TheRedStapler Interest in wine and tours shot up like crazy after the film came out]]; it even affected the sales of certain wines. Miles's love of pinot noir caused that wine's sales to soar, while his disparaging of Merlot ("If anyone orders Merlot, I'm leaving; I am NOT drinking any FUCKING Merlot!") caused Merlot's sales to dip, although it continues to be the most prevalent wine in the States.

Also bizarrely got [[ForeignRemake a remake by the Japanese.]]


!! This movie contains examples of:

* TheAlcoholic: Miles.
* AskAStupidQuestion: Miles pleads Jack not to do this in wine country, being the InsufferableGenius Miles is.
* BigBeautifulWoman: The waitress at the barbeque restaurant. ('Betcha that chick's two tons of fun.')
* BerserkButton: Miles will ''not'' drink any [[PrecisionFStrike fucking]] merlot. He'd also appreciate it if you didn't bring up his wife getting re-married or his affair during that marriage.
* BigShutUp: Miles when Jack won't stop talking while he's trying to take a golf swing.
-->'''Miles''': Shut up, shut up, SHUT UP! JESUS CHRIST, WHAT THE HELL IS WRONG WITH YOU, WOULD YOU PLEASE '''JUST SHUT UP'''! FUCK!
* BookEnds: The movie starts and ends with a knock on the door.
* CanNotSpitItOut: Miles's affection for Maya.
* ComicallyMissingThePoint: [[spoiler: After learning his latest novel will not be published,]] Miles bemoans that he's so insignificant that he cannot commit suicide. Instead of sympathetic uplifting, Jack helpfully points out that John Kennedy Toole of ''AConfederacyOfDunces'' committed suicide [[spoiler: before he was published.]]
* CreatorCameo: Off-screen, but it's Rex Pickett, who wrote the novel the film is based on, that hits Miles's golf shot that smacks into the rude golfer's cart.
* ADateWithRosiePalms: Implied with Miles after Jack and Stephanie go off on their own. He also drinks wine while [[IReadItForTheArticles reading the articles.]]
* DeadpanSnarker: Miles when sober.
* DidNotGetTheGirl: [[spoiler: The film ends with Miles looking to rekindle their friendship.]]
* DidYouJustHaveSex: Jack wants details after Miles come back from a night with Maya.
* {{Doorstopper}}: Miles lends Maya a manuscript of his novel. He gives her a decently sized chunk of paper...then goes back for another one just as big.
* DrowningMySorrows: Miles does this often. Very often.
* DVDCommentary: Giamatti and Church do one for the film that is almost as hilarious as the film itself, thanks to their endless SelfDeprecation.
* TheEeyore: Miles when drunk or depressed.
* EvenTheGuysWantHim: Jack claims to be this.
* EveryoneCanSeeIt: Jack immediately notices the [[UnresolvedSexualTension UST]] between Miles and Maya; Jack even tries to help Miles with this.
* EveryoneIsSingle: To Maya and Stephanie, this looks to be this trope in perfect form, but of course we know that isn't true when it relates to Jack.
* ExecutiveMeddling: In-universe: [[spoiler: A publication house passes on Miles' novel, saying that they liked it but did not know how to market it.]]
* FallingInLoveMontage: Miles and Maya spend a nice day-and-a-half falling for each other to Rolfe Kent's beautiful jazzy piano score.
* FanDisservice: If you came to see Virginia Madsen naked, you came to the wrong place. If you came to see [[Film/ConAir M.C.]] [[Series/{{LOST}} Gainey]] naked...
* FashionDissonance: Jack is watching some sort of spring break event on TV, but the hairstyles and blindingly-neon swimwear is clearly early-90's. The filmmakers had asked MTV for usage of spring break footage, but the channel was only willing to give them dated material free-of-charge.
* TheFilmOfTheBook
* AFriendInNeed:
** Jack when he asks Miles to go back to the house of the waitress he slept with to retrieve his wallet, [[spoiler: which has his wedding rings in them]]. Miles is in disbelief, but relents after an impassioned plea.
** To a lesser extent, Jack. He's always -- well, almost always -- looking out for Miles to make sure his friend doesn't tip further into alcohol abuse and depression.
* FunnyBackgroundEvent: When the quartet are hanging at Stephanie's house and Miles and Maya go back into the living room, you can hear Jack doing his advertising voiceover while fooling around with Stephanie in her room ("Now for a low, low 5.9%...")
* GetItOverWith: Miles's response to Jack's request to [[spoiler: total his car once more to look like they were in an accident bad enough to explain Jack's facial injuries that he actually received from another woman.]]
* HandsomeLech: Jack. All it takes is a smile and some banter and he's in.
* HeroicBSOD:
** Miles has one when Jack reveals Miles' ex-wife is getting re-married and Jack held that information back.
** Then another after [[spoiler: Miles tells Maya that Jack is getting married, which causes her to break contact with him]]. Miles even curls up in the fetal position on his motel bed, although it's played for laughs.
-->'''Jack''': Let me call you back...it's OK, it's just Miles, he's having one of his breakdowns.
* IKnowWhatWeCanDoCut: After one of the BSOD moments above, Jack says he knows what Miles needs, and the scene shifts to Jack taking Miles to the unfortunately-named Frass Canyon winery. A deleted scene also shows Jack taking Miles to Champs Sports for new shoes as a payoff for an earlier line in the movie; it's also why Miles is holding the store bag when they arrive back at the inn.
* ImAManICantHelpIt: Jack's rationalization to getting laid before getting married.
* InsufferableGenius: Miles. It's so deep that the one of the main reasons he can't let go of his ex and his attraction to Maya is that they're both equally astute about wine as he is.
** A visual example, pointed out on the DVD commentary, is that Miles always does the Times crossword puzzle ''in pen''.
* JerkAss: Both Miles and Jack have traits of this; Miles steals money from his mother for the trip, Jack has a goal of sleeping with other women before he gets married. It is one of the film's greatest triumphs that they win us over as eventual [[JerkWithAHeartOfGold jerks with a heart of gold]].
* KarmaHoudini: Jack, for the most part. [[spoiler: Despite sleeping with two different women on the trip, including the day before his wedding and lying about it to his fiancee, he ends up happily married to her as scheduled. Prior this though, when one of those women learns he's getting married, Jack gets his face smashed, so he doesn't escape karma entirely.]]
* TheLadette: Stephanie, who rides motorcycles, smokes weed, drinks, and is in as constant a state of horny as Jack.
* TheLoinsSleepTonight: Jack believes this for Miles when he's depressed after a night at Maya's.
* LoveEpiphany: Only when Jack [[spoiler: loses his wedding rings]] does he fully realize how much his fiancee and his impending marriage mean to him.
* MakeItLookLikeAnAccident: Jack does this [[spoiler: to Miles's car to give an explanation to his fiancee how he bashed his face in, instead of the actual story that the girl he hooked up with during the week did that to him upon learning of said impending nuptials.]]
* MeaningfulEcho: The knocking that opens and closes the film.
* MostWritersAreWriters: Are you a sad, melancholic would-be author? Then there's an impossibly gorgeous blonde out there waiting to fall in love with you.
* MyGreatestFailure: [[spoiler: Miles's book doesn't get published. His agent even expresses sympathy that he's written "a really good book with no home."]]
* MythologyGag: Shares the same universe as ''Film/{{Election}}'', since both films were directed and partially written by AlexanderPayne. Look for the principal from the high school from ''Film/{{Election}}'' at the country club, who even appears in the credits as "Vacationing Dr. Walt Hendricks".
-->''(Jack and Miles are talking about Maya while walking by a golfer and his son)''\\
'''Jack:''' Don't you just want to feel that cozy little box grip down on your johnson? \\
'''Vactioning Dr. Walt Hendricks:''' Hey, you mind keeping it down, buddy?
* NakedPeopleAreFunny: The scene in which Miles has to retrieve Jack's wallet, walks in on a couple having sex and is chased off by the naked husband.
* NaughtyByNight: According to Jack, this is Stephanie. ("She is NASTY, Miles! Nasty, nasty, nasty!")
* NoHoldsBarredBeatdown: [[spoiler: Stephanie beats the crap out of Jack after learning that he's engaged, forcing him to go to the ER to fix his face.]]
* NoodleIncident: It is mentioned only once that Miles had an affair with someone else during the downfall of his marriage.
* NowOrNeverKiss: Miles tries this at one point. Maya elects to leave immediately, but gives him a pity hug and peck before departing.
* OddCouple: Miles and Jack have very few things, if anything, in common, and yet have remained best friends since being college roommates.
* OhCrap: Miles's look when [[spoiler: he accidentally slips to Maya that Jack is getting married.]]
* OneLastFling: Jack's mission for the trip.
* PrecisionFStrike:
** Maya's capping sentence to her monologue to Miles, describing how wine just coming off its peak into its decline tastes "so fucking good"; she's also implying to Miles she thinks the same of him as she does wine.
** Also, [[spoiler: when she accuses Miles of not revealing that Jack was engaged while screwing her friend until after Miles slept with her: "But you wanted to fuck me first!" It's the bluntly honest use of the word that makes Miles more ashamed of himself.]]
** Miles' use of it emphasizes his disdain of Merlot ("I am NOT drinking any FUCKING Merlot!")
* RightThroughTheWall: A nice conversation between Miles and Maya turns into awkward silence as the lovemaking between Jack and Stephanie in the other room suddenly becomes audible.
* RoadMovie: Slightly subverted in that the journey isn't part of the plot itself, just as a means for the characters to get away from it all.
* RunningGag: Jack's {{Noob}} responses to Miles' wine critiques ("Tastes pretty good to me!"), as well as telling everyone that Miles is a published author when that is not true.
* SceneryPorn: The luscious cinematography of the beautiful Santa Barbara County wine country.
* SensitiveGuyAndManlyMan: Miles and Jack, respectively.
* SeriousBusiness: Miles and wine.
* SexEqualsLove: Miles and Maya.
* ShipperOnDeck: Jack for Miles/Maya.
* SideEffectsInclude: Invoked when Jack is reciting one of the adverts he did.
* SingleWomanSeeksGoodMan: Maya.
* TheSmurfettePrinciple: Averted in that the two women in the story are crucial in the CharacterDevelopment for the two male leads.
* SorryToInterrupt: Miles when he walks in on Jack and Stephanie. ("Not now, not now!")
* {{Subtext}}: Miles and Maya's conversation on the porch about their love of wine.
* SuperSenses: Miles when it comes to wine; he can even detect vegetables and cheeses in wine. Compare to real wine tasters, who have been known to lambast wine from one bottle and simultaneously lend glowing praise to another bottle from the exact same batch, simply because some bright spark managed to convince them that the second bottle was from a vintage that cost $30 more.
* TelevisionGeography: Averted for most of the film; most of the locales are real (such as the Hitching Post restaurant), in the correct places, and some even use their actual employees. Notable exceptions would be that Miles' apartment complex in San Diego and a panning shot of Miles' mother's complex in Oxnard are actually in Santa Maria, CA.
* TrailersAlwaysSpoil: Nearly every key plot point and revelation is found in the trailer, including [[spoiler: the women finding out Jack is getting married, and that Jack indeed ends up getting married in the end.]]
* UnresolvedSexualTension: Miles and Maya, which their friends quickly notice.
* UpToEleven: Jokingly invoked on the commentary. Paul Giamatti points out that the actress playing Jack's fiance is about six inches taller than both the actors playing her parents as all three stand side-by-side.
* VitriolicBestBuds: Jack and Miles.
* WhatDoesSheSeeInHim: Part of Miles' reluctance to pursue Maya is that he feels she's a bit out of his league. After all, she is a middle-aged hottie, and he's, well, Paul Giamatti.
* WhatTheHellHero: Jack gives him a few WTH remarks (or more like [[PrecisionFStrike "What the fuck?!"]]) when he's exasperated about Miles not making a move on Maya because of his depressed yearning for his ex.
* WineIsClassy: TheMovie!
* WomanScorned: [[spoiler: Stephanie's reaction to learning Jack's getting married in a few days? She pounds his face in with her motorcycle helmet.]]
* YouNeedToGetLaid: Verbalized word-for-word from Jack to Miles; he elaborates that it will be his gift to his best man to help him get laid during the trip.
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