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Film / Sideways

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A 2004 comedy/drama film directed and co-written by Alexander Payne.

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, adventurous, wine pourer who instantly takes Jack up on his charming advances.

Hilarity, and bittersweetness ensue. (And wine drinking. Lots and lots of wine drinking.)

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.
  • Actually Pretty Funny: After a naked and beat-up Jack shows up at the inn having ran for miles when his fling's husband showed up, including running through an ostrich farm ("those fuckers are mean!"), Miles goes from concerned to laughing his ass off at Jack's Laser-Guided Karma for the week.
  • Adaptation Name Change: In the novel, Maya's friend is named Terra. In the film, her name is changed to Stephanie.
  • The Alcoholic: Miles; he may think he's merely an oenophile, but he's really just a drunk.
  • Ambiguous Situation: Early on, it is established that not only is Miles prone to lying to cover up his drunken shortcomings, but Jack is able to see through them. After Stephanie breaks Jack's nose, Miles denies telling Maya about the wedding, and pins the blame on a bartender they spoke to earlier. Jack mulls it over and doesn't seem to buy it. Wrecking Miles' car to explain the broken nose may have also been Jack's way of getting back at Miles.
  • Apathetic Teacher: Miles's job goes unmentioned until near the end of the film, but when we see a shot of him teaching his class after the road trip is over he looks thoroughly disengaged. (Though it's not clear whether he's always like this in class, or is specifically distracted by the events of the road trip.)
  • Ask a Stupid Question...: Miles pleads Jack not to do this in wine country, being the Insufferable Genius Miles is.
  • 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.
  • Beware the Nice Ones: Stephanie is spirited and kind, but she did break Jack's nose when she figured out the truth.
  • Big Beautiful Woman: The waitress at the barbeque restaurant; Jack immediately (and successfully) hits on her.
    Jack: Betcha that chick's two tons of fun, you know, the grateful type.
    Miles: [annoyed] I wouldn't know about that.
  • Big "SHUT UP!":
    • Miles when Jack won't stop talking while he's trying to take a golf swing.
    • Miles again when Jack brings up the subject of his infidelity ("Shut up, shut your face! Shut up!"). Easily Miles' most firmly assertive and arguably his angriest moment in the film; he's not messing around when it comes to that subject, which Jack immediately drops.
  • Bitch in Sheep's Clothing: When Jack is fed up with Miles's obsession with getting Victoria back in his life, he reminds him of "all the bad times you had with Victoria, how small she could make you feel", which is why Miles had an affair during their marriage as it was falling apart.
  • Blatant Lies: Both Miles and Jack are prone to telling lies to cover up their less admirable qualities (Miles' drinking and Jack's philandering). The two friends have known each long enough to see through them.
  • Book Ends: The movie starts and ends with a knock on the door.
  • Bittersweet Ending: Miles' wife is moving on, and his novel is probably never going to get published, but he still might have a chance with Maya.
  • Cannot Spit It Out: Miles's affection for Maya.
  • Chekhov's Gun: Miles's unopened 1961 Chateau Cheval Blanc, which he was saving for a special occasion worth celebrating. When seemingly hitting rock bottom by the end of the movie, he glumly drinks it out of a Styrofoam cup with a fast-food meal.
  • Central Theme: Letting go. Jack and Miles are both living in the past; Jack's early acting success with the womanizing and party days that came with it, Miles still holding on to his (perhaps not as happy as he remembers) marriage and his great, but unpublishable novel. Miles's drinking the Cheval Blanc after Jack's wedding shows he's finally ready to move on with his life.
  • 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.
  • Contrived Coincidence: Stephanie, a wine pourer who serves Miles and Jack during their tour of Santa Barbara wine country, somehow just so happens to be friends with Hitching Post waitress Maya back in Buellton, whom Miles already knows from his past visits, setting up the main quartet of characters.
  • 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.
  • Deadpan Snarker: Miles when sober.
  • 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 chunk of paper...then goes back for another one just as big.
  • Double Meaning: While relaxing on Stephanie's patio, Maya asks Miles why he prefers pinot noir above all others. Miles talks about how pinot noir is so difficult to craft because the namesake grapes are notoriously thin-skinned and "temperamental", but that with enough care and attention, the taste is unlike any other - in essence, he's also describing himself. When he in turn asks Maya how she got into wine, she talks about her fascination with the complexity and ever-shifting tastes of wine in general, that a wine can even be at its best when beyond its peak - which doubles for her affection towards Miles even when he visibly is carrying personal baggage. And in case Miles missed the subtext, Maya reaches out and holds his hand when she makes her point.
  • Double-Meaning Title: The title refers to the way wine is stored, and that both the main characters are sort of stuck, holding on to unhealthy and immature behaviors.
  • Drowning My Sorrows: Miles does this often. Very often.
  • The Eeyore: Miles when drunk or depressed.
  • Establishing Character Moment: At the beginning of the movie, a hungover Miles gives an excuse to Jack about why he's going to be late picking him up, and lazily goes about his morning routine with no urgency. When arriving at Jack's house, he blames it on bumper-to-bumper traffic (it was smooth sailing on the freeway). Jack has been friends long enough with Miles to see right through it. Invoked by Giamatti on the commentary when he points out Miles prefers the "dark" cake for Jack's wedding as well.
  • Even the Guys Want Him: Jack claims to be this.
  • Everyone Can See It: Jack immediately notices the UST between Miles and Maya; Jack even tries to help Miles with 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.
  • Executive Meddling: In-universe: 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.
  • 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...
  • Fashion Dissonance: 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.
  • The Film of the Book
  • Flat "What": Miles's response when Jack asks him to go back to the waitress's house to reclaim his wallet.
  • 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.
  • Gilligan Cut: Jack is already miffed that Miles is stopping at his mom's house on her birthday on the way to wine country, and gets more so when Miles takes her up on her offer for food.
    Mrs. Raymond: Make yourselves comfortable! You boys hungry?
    Miles: Yeah, I'm hungry! (Jack gives him an annoyed look) Just a snack.
    (cut to them finishing off a buffet of food hours later with Jack shooting a Death Glare across the table)
  • Got Volunteered: Jack asks Miles to help him to get his wallet back from the waitress's house. Once they get there, Miles gets more than he bargained for, as usual.
    Miles: So what's the plan?
    Jack: The plan go.
  • 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.
    • Then another after 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's OK, it's just Miles, he's having one of his breakdowns.
  • Hypocritical Humor: When Miles wants to stop in Oxnard to see his mom (and more importantly, steal trip money), Jack is annoyed before Miles cuts him off saying it's her birthday. Jack apologizes and asks how old she is, to which Miles offers a disinterested "Oh, seventy....something" and signs and seals her birthday card in the parking lot.
  • I Can Explain: Jack while Stephanie beats him down with her motorcycle helmet to no avail.
  • "I Know What We Can Do" Cut: 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.
  • I'm a Man; I Can't Help It: Jack's rationalization to getting laid before getting married.
  • I Need a Freaking Drink: Miles's typical and immediate response to bad news, like when he learns his ex-wife is newly married, or Maya having the night off when he goes to the restaurant just to see her, or that his book isn't being published.
  • I Need to Go Iron My Dog: While the quartet are out to dinner, Miles gets hammered and drunkenly dials his ex-wife for a bitter conversation about her impending marriage. When he comes back to the table, he's visibly irritated, which leaves an awkward silence around the table. Stephanie silently signals to Maya to go to the bathroom with her right then so that Jack and Miles can hash things out alone.
  • 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.
    • A visual example, pointed out on the DVD commentary, is that Miles always does the Times Crossword Puzzle in pen.note 
  • 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 hearts of gold.
  • Karma Houdini: Reconstructed with Jack. He sleeps with two different women on the trip, including the day before his wedding. When one of these women learns he's getting married, Jack gets his face smashed. To explain the broken nose to his fiancée, Jack runs Miles' car into a tree, giving the appearance they had been in an accident. It appears that Jack feels real remorse and really wants to go back to his fiancee, which sort of "earns him" a second chance. Ultimately, Jack ends up happily married to her as scheduled.
  • The Lad-ette: Stephanie, who rides motorcycles, smokes weed, drinks, and is in as constant a state of horny as Jack.
  • Liar Revealed: Jack spends most of the first two acts pretending to be single. Needless to say, when Stephanie finds out he's getting married next weekend, she doesn't take it well.
  • 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.
  • Male Gaze: When meeting Maya for the first time, Jack's eyes linger on her chest for a moment or two.
  • Maybe Ever After: Miles and his wife are never getting back together, but he and Maya may have a future.
  • Meaningful Echo: The knocking that opens and closes the film.
  • Mood Whiplash: Stephanie while beating the crap out of Jack once she knows the truth about him.
    Stephanie: [angry] You're getting married on Saturday?! What about that shit you said to me! [sobbing] You said you loved me! [angry] I HOPE YOU DIE!
  • Most Writers Are Writers: Are you a sad, melancholic would-be author? Then there's an impossibly gorgeous blonde out there waiting to fall in love with you (and your unpublished, unappreciated magnum opus).
  • My Beloved Smother: When Miles stops by his mom's house to say happy birthday (and swipe money for the trip), she insists he stay the night and meet up with relatives the next day, keeps him there with a giant meal when he and Jack are on their way elsewhere, and unknowingly pours salt in the wound when she suggests he should get back with his ex-wife, whom he already still yearns for.
  • My Girl Is a Slut: Suffice to say that the waitress's husband is a lot less angry with her for stepping out on him with Jack than you'd normally expect.
  • My Greatest Failure: Miles's book doesn't get published. His agent even expresses sympathy that he's written "a really good book with no home."
  • Mythology Gag: Shares the same universe as Election, since both films were directed and partially written by Alexander Payne. 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?
  • Naked People Are Funny: 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. Giamatti noted this trope is the only way Alexander Payne will put a sex scene or nudity in his movie (see also: About Schmidt).
  • Nasal Trauma: Jack gets smashed him in the face by a motorcyle helmet-wielding Stephanie, breaking his nose. He spends the rest of the film wearing a nasal splint, and has to crash Miles' car into a tree to make it look as if they've been in an accident.
  • Naughty by Night: According to Jack, this is Stephanie. ("She is NASTY, Miles! Nasty, nasty, nasty!"). Also the waitress who hooks up with Jack; she comes across as a fawning fangirl, but when Miles pays an unexpected visit, she's having wild sex with her husband with both being turned on by him catching her having anal sex with Jack.
  • Nice Girl: Both Maya and Stephanie. Even though Stephanie can still bust Jack's nose when she discovers the truth.
  • 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.
  • Oblivious to Love: Miles doesn't notice when Maya is coming onto him. Justified because he's depressed and assumes nobody would ever love him.
  • 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.
  • P.O.V. Cam: Uses this perspective when Miles is scanning the waitress's bedroom for Jack's wallet, and zooms in when he spots it on the dresser.
  • 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!")
  • Rattling Off Legal: Jack mentions to Maya that he mainly does "voiceover" roles currently, and reveals this trope is his particular work.
    Jack: [radio voice] Now with a low, low 5.9% APR financing!
    Maya: That's hilarious, you sound just like one of those guys!
    Jack: I am one of those guys!
    Maya: You are not!
    Jack: [radio voice] Consult your doctor before using this product, side effects may include oily discharge, hives, loss of appetite, low blood pressure, if you have diabetes or a history of kidney're dead, asshole!
  • 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.
  • Road Trip Plot: 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.
  • 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, who consummate once their feelings are finally on the same wavelength.
  • Sexy Discretion Shot: When Maya pulls Miles into her apartment, the camera stays outside and the time of day changes from night to day, with Miles asleep in her bed.
  • Shipper on Deck: Jack for Miles/Maya.
  • Side Effects Include...: Invoked when Jack is reciting one of the adverts he did.
  • Single Woman Seeks Good Man: Maya.
  • Sommelier Speak: Miles likes to hold forth on the profile of every wine they drink; Jack's answer is always "tastes pretty good to me."
  • Sorry to Interrupt: Miles when he walks in on Jack and Stephanie. ("Not now, not now!")
  • Starts Stealthily, Ends Loudly: Miles takes several minutes quietly breaking into the waitress's house (with her husband inside as well) to find Jack's wallet, and finds to his horror it's in her bedroom (and for further horror, while she and her husband are having wild sex over her being caught with Jack earlier). Realizing he'd have a head start with their position, he simply runs in, grabs it, and dashes out with the naked old husband in angry pursuit.
  • Subtext: Miles and Maya's conversation on the porch about their love of wine. (Or at least Maya's side of the conversation - Miles is talking exclusively about wine doesn't seem to notice Maya's hints.)
  • Super-Senses: Miles when it comes to wine; he can even detect vegetables and cheeses in wine. This is Truth in Television among serious oenophiles, who tend to describe a wine's flavors in intricate detail. Played for Laughs in contrast to Jack, whose reaction to every single wine is to go "I don't know, it tastes pretty good to me."
  • 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.
  • 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.
  • Vitriolic Best Buds: Jack and Miles.
  • Wedding Ring Defense: Discussed by Jack. Miles is reluctant to talk to Maya initially because last time they spoke she was wearing a ring. Jack says that his current fiancee Christine did, too, but it was just to ward off unwanted suitors and he wasn't fooled—"How do you think I met her?" He later informs Miles that Maya doesn't have the ring on anymore.
  • 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 beautiful and completely confident, 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. Maya gives him a particularly scathing one after she finds out Miles had been withholding the fact Jack is getting married on Saturday and is just messing around with Stephanie under the guise of something serious between them.
    Miles: Please believe me, Maya, I was going to tell you last night, but—
    Miles (defeated):
    Maya: Yeah.
  • Wine Is Classy: Deconstructed Trope: As educated and cultured as Miles is about wine, his interactions with his ex-wife make it clear he's still just a drunk.
  • 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.


Video Example(s):


No Merlot

Miles makes it clear just how much he hates Merlot.

How well does it match the trope?

5 (4 votes)

Example of:

Main / PrecisionFStrike

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