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A critically acclaimed 2004 comedy/drama. Middle-aged BFFs Miles (Paul Giamatti) 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 just wants to drink as he's clinically depressed about his divorce (two years and counting) and failure to get his novels published; Jack 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 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, heartwarming, 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 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 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".

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 a remake by the Japanese.

This movie contains examples of:

  • Actor Allusion: Thomas Haden Church's character is a former TV star now doing commercial voiceovers, which mirrors Church's own career.
  • Ask a Stupid Question: Miles pleads Jack not to do this in wine country, being the Insufferable Genius Miles is.
  • BBW: The waitress at the barbeque restaurant. ('Betcha that chick's two tons of fun.')
  • Berserk Button: Miles will not drink any fucking merlot.
    • He'd also appreciate it if you didn't bring up his wife getting re-married or his affair during that marriage.
  • Book Ends: The movie starts and ends with a knock on the door.
  • Cannot Spit It Out: Miles's affection for Maya.
  • Comically Missing the Point: 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 A Confederacy of Dunces committed suicide before he was published.
  • Creator Cameo: 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.
  • A Date with Rosie Palms: Implied with Miles after Jack and Stephanie go off on their own. Although being the classy man he thinks he is, he drinks wine while reading the articles.
  • Did You Just Have Sex?: 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 chuck of paper...then goes back for another one just as big.
  • Drowning My Sorrows: Miles does this often. Very often.
  • The Eeyore: Miles when drunk or depressed.
  • Even the Guys Want Him: Jack claims to be this.
  • Everyone Is Single: 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.
  • Deadpan Snarker: Miles when sober.
  • Did Not Get the Girl: The film ends with Miles looking to rekindle their friendship.
  • DVD Commentary: Giamatti and Church do one for the film that is almost as hilarious as the film itself, thanks to their endless Self-Deprecation.
  • Executive Meddling: In-universe: A publication house passes on Miles' novel, saying that they liked it but did not know how to market it.
  • Everyone Can See It: Jack immediately notices the UST between Miles and Maya; Jack even tries to help Miles with this.
  • Fan Disservice: If you came to see Virginia Madsen naked, you came to the wrong place. If you came to see M.C. Gainey naked...
  • "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.
  • The Film of the Book
  • A Friend in Need: Jack when he asks Miles to go back to the house of the waitress he slept with to retrieve his wallet, 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.
  • Funny Background Event: 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%...)
  • Get It Over With: Miles's response to Jack's request to 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.
  • Handsome Lech: Jack. All it takes is a smile and some banter and he's in.
  • Heroic BSOD: Miles has one when Jack reveals Miles' ex-wife is getting re-married and Jack held that information back.
  • Hey, It's That Guy!: The four main cast members have a litany of supporting roles on their resumes. Virginia is also known as the sister of a certain other Madsen.
    • Also invoked in-universe. A waitress recognizes Jack from his stint on Days of Our Lives, which he parlays into sleeping with her.
    • Shares the same universe as Election, since both films were directed and partially written by the same person. Look for the principal from the high school from 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?

  • I'm a Man, I Can't Help It: Jack's rationalization to getting laid before getting married.
  • Insufferable Genius: 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.
  • 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 jerks with a heart of gold.
  • Karma Houdini: Jack. 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 on Saturday.
    • Conversely, he does get his face smashed (see Woman Scorned, below).
  • The Ladette: Stephanie, who rides motorcycles, smokes weed, drinks, and is in as constant a state of horny as Jack.
  • The Loins Sleep Tonight: Jack believes this for Miles when he's depressed after a night at Maya's.
  • Love Epiphany: Only when Jack loses his wedding rings does he fully realize how much his fiancee and his impending marriage mean to him.
  • Make It Look Like an Accident: Jack does this 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.
  • Meaningful Echo: The knocking that opens and closes the film.
  • MILF: Stephanie.
  • My Greatest Failure: Miles thinks his third attempt to get published may be his best, and Maya ends up loving it. It doesn't get published.
  • Naughty by Night: According to Jack, this is Stephanie. ("She is NASTY, Miles! Nasty, nasty, nasty!")
  • No-Holds-Barred Beatdown: Stephanie beats the crap out of Jack after learning that he's engaged, forcing him to go to the ER to fix his face.
  • Noodle Incident: It is mentioned only once that Miles had an affair with someone else during the downfall of his marriage.
  • Now or Never Kiss: Miles tries this at one point. Maya elects to leave immediately, but gives him a pity hug and peck before departing.
  • Odd Couple: Miles and Jack have very few things, if anything, in common, and yet have remained best friends since being college roommates.
  • Oh Crap: Miles's look when he accidentally slips to Maya that Jack is getting married.
  • One Last Fling: Jack's mission for the trip.
  • Precision F-Strike: 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, 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!")
  • Romance on the Set: Sandra Oh was married to director Alexander Payne. They divorced shortly after.
  • Road Movie: 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.
  • Running Gag: 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.
  • Right Through the Wall: 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.
  • Scenery Porn: The luscious cinematography of the beautiful Santa Barbara County wine country.
  • Sensitive Guy and Manly Man: Miles and Jack, respectively.
  • Serious Business: Miles and wine.
  • Sex Equals Love: Miles and Maya.
  • Single Woman Seeks Good Man: Maya.
  • The Smurfette Principle: Averted in that the two women in the story are crucial in the Character Development for the two male leads.
  • Sorry to Interrupt: Miles when he walks in on Jack and Stephanie. ("Not now, not now!")
  • Star-Making Role: Paul Giamatti, from character actor to now having the clout for billing on movies.
  • Subtext: Miles and Maya's conversation on the porch about their love of wine.
  • Super Senses: 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.
  • Television Geography: 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.
  • Throw It In: In film reviews, it is suggested that Miles is very self-absorbed in his own intelligence because he does the New York Times crossword in pen (while driving!). This was not intentional; the crew simply gave Paul Giamatti a pen because that was all they had on hand, but it indeed works for the character nonetheless.
  • Trailers Always Spoil: Nearly every key plot point and revelation is found in the trailer, including the women finding out Jack is getting married, and that Jack indeed ends up getting married in the end.
  • Unresolved Sexual Tension: Miles and Maya, which their friends quickly notice.
  • Up to Eleven: 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.
  • Vitriolic Best Buds: Jack and Miles.
  • What Does She See in Him?: 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.
  • What the Hell, Hero?: Jack gives him a few WTH remarks (or more like "What the fuck?!") when he's exasperated about Miles not making a move on Maya because of his depressed yearning for his ex.
  • Wine Is Classy: The Movie!
  • Woman Scorned: Stephanie's reaction to learning Jack's getting married in a few days? She pounds his face in with her motorcycle helmet.
  • You Need to Get Laid: 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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