Jack (Thomas Haden Church) pours wine over his head as Miles (Paul Giamatti) watches in a bar
Film review

Sideways

2004 · Directed by Alexander Payne · 2h 07m · MPA R

In a sentenceA holiday with two men we would avoid at breakfast and worry about all day

Two friends head into wine country on a road trip. Miles (Paul Giamatti) brings a knowledge of wine and a store of disappointments; Jack (Thomas Haden Church) approaches their time together rather differently. As they taste and talk, their friendship becomes caught up in questions of middle age, pleasure and romance. Virginia Madsen plays Maya and Sandra Oh plays Stephanie. Alexander Payne directs this comedy-drama, adapted by Payne and Jim Taylor from Rex Pickett’s novel, about men trying to enjoy themselves while struggling with the lives they have.

Fi1m review

Alexander Payne’s wine-country comedy is funny, patient and unusually tender towards its difficult men. Paul Giamatti and Thomas Haden Church make the friendship convincing, though a slack middle and occasional cheap jokes need forgiving.

Alexander Payne’s Sideways is an excellent comedy about the effort involved in spending time with a disappointed friend. It takes the familiar road-trip pairing of two mismatched men and lets their conversation become more revealing than either would wish. The wine matters because it gives them something to do, and Miles something he can talk about with confidence. Payne and his co-writer Jim Taylor, adapting Rex Pickett’s novel, understand how a subject someone knows well can become an excuse to avoid everything else.

Paul Giamatti gives Miles’s wine talk the painstaking seriousness of a man who expects to be challenged. The precision is funny, especially when set beside his less successful dealings with people. We laughed, then felt rather sad for him. It was the care he gave those judgements that did it: Giamatti makes an opinion about wine sound like something Miles badly needs to get right. He lets the self-pity become tiresome, too, and trusts us to remain interested.

Thomas Haden Church’s Jack gives Giamatti someone who will not join him in examining every discomfort. Church’s ease is funny in itself, and he makes Jack’s lack of reflection feel like a habit Miles both resents and needs. The friendship is convincing because neither actor makes being together look consistently enjoyable. Virginia Madsen, as Maya, and Sandra Oh, as Stephanie, are equally persuasive, especially when the men stop being charming. We wanted more of the film’s attention to stay with them, rather than returning so reliably to the men’s troubles.

Phedon Papamichael’s cinematography lets us enjoy the wine country without suggesting that the view ought to cure anyone. The pleasure of looking around helps when the men become less pleasurable company. Jane Ann Stewart’s production design makes the places where they taste wine feel comfortable enough for Miles to settle into his subject. That relaxed setting gives Giamatti room to make wine tasting seem like serious work.

Kevin Tent’s editing generally gives the conversations enough time to become uncomfortable before moving on. We can register an embarrassment without having every joke pointed out. The middle does drift, though, and at 127 minutes the film gives some exchanges longer than they need. Rolfe Kent’s music lends those passages some lift, but cannot quite supply the missing momentum. His score is otherwise a good companion, light enough to let the sadness arrive without a musical warning.

Payne is less assured when he reaches for broader humiliation. A few jokes ask us to enjoy the men’s embarrassment in a simpler way than the performances have prepared us for, and the change feels cheap. The sharper comedy comes when these friends fail to listen to each other. For a buddy film, it is unusually willing to let companionship feel like work.

We would give it an unhurried evening, with one reservation. Anyone hoping for amiable holiday company may tire of Miles before Payne does. Stay for Giamatti, especially if someone else’s expertise has ever made a dinner feel longer than planned.

Critical consensus AI synthesised

88
Positive
15
Mixed
0
Negative
0

Most critics like Sideways a great deal, and the praise lands in the same two places: the writing and Paul Giamatti. Payne and Taylor’s script is credited with drawing two flawed, middle-aged men so exactly that critics find them likeable without being flattered, and several reviews note that the film is funny and sad in equal measure. Giamatti’s depressive Miles is singled out almost everywhere, with Thomas Haden Church close behind, and the pairing itself gets as much credit as either performance. The wine-country setting and the tasting scenes are mentioned repeatedly as more than decoration.

The spread is narrow. Reservations are minor: Empire notices a slight sag in the second act, and Slant Magazine, the coolest of the fifteen, objects to a late contrivance and to Payne’s fondness for cheap jokes even while admiring his structure and his cast. Nobody else sees much wrong with it, and more than one finds it lighter and better than Payne’s earlier films.

RogerEbert.com
28 October 2004 · ★★★★/4 · Roger Ebert
100

Ebert calls the film lovable and as wonderful as Fargo, praising its complex characters, necessary ensemble, and Payne's direction that distributes happiness where deserved.

Read the full review →
Empire
1 January 2012 · Dan Jolin
90*

The critic praises Payne and Taylor's script for its sharp observation of flawed, relatable characters and the uniformly excellent performances, especially Paul Giamatti's. Minor flaws like a slight second-act sag do not detract from the wonderful, original result.

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Los Angeles Times
22 October 2004 · Kenneth Turan
90*

Turan praises the counterintuitive triumph of turning morally sketchy characters into a satisfying movie through exact writing, precise directing, and transcendent acting, highlighting its emotional reality and maturity.

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The AV Club
18 October 2004 · Scott Tobias
90*

The critic calls the film a wonderful road comedy that uses wry behavioral observations and wine as a metaphor for life. He singles out Giamatti's performance and the film's ability to blend comedy with emotional resonance and intimacy.

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The Guardian
28 January 2005 · Peter Bradshaw
90*

This is a glorious, bittersweet comedy of male friendship and midlife crisis, even better than Payne's prior films, and a new classic of American cinema comparable to Cassavetes or Ashby. The critic singles out the beautifully written and acted observations, sight gags, and exquisite sadness that give the film its emotional power.

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The Hollywood Reporter
12 September 2004 · Kirk Honeycutt
90*

The critic praises the film as a hysterically funny yet melancholy comedy with a beautiful structure, buoyant romance, and tight control of subtext. He highlights the strong pairing of Giamatti and Church and the effective use of the wine country setting.

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Straight answers AI written, from our review

Is Sideways worth watching?
Sideways is worth watching for anyone who enjoys patient, talkative comedy about difficult men, and we scored it 86. Paul Giamatti and Thomas Haden Church make the friendship convincing, though the middle drifts and a few jokes are cheaper than the performances deserve. Anyone hoping for amiable holiday company may tire of Miles before the film does.
How long is Sideways, and what is it rated?
Sideways runs 2h 07m and is rated R by the MPA in the US. It is a comedy and drama film.
Where can I watch Sideways in the US?
Sideways is available to rent from Amazon Prime Video and Apple TV from $3.99. Availability is checked daily; the links above go straight to each service.
How violent or frightening is Sideways, and is it suitable for children?
Sideways is a UK 15 comedy-drama with no violence or frights to speak of; the certificate reflects adult language and sexual content rather than anything alarming. It is not a film for children, less because of what it shows than because its humour rests on middle-aged disappointment and embarrassment. Older teenagers with patience for conversation may find something in it.
How does Sideways compare to Withnail & I?
Sideways and Withnail & I are both fraught holidays with self-pitying men whose company is hard to give up, but Alexander Payne's film is the warmer and more forgiving of the two. Bruce Robinson's is sharper, sadder and more tightly written, with the funnier lines. Choose Sideways for tenderness and wine-country patience, Withnail & I for bite.
Is Sideways based on a true story or a book?
Sideways is not a true story; it is adapted by Alexander Payne and Jim Taylor from Rex Pickett's novel of the same name. Our review does not weigh how closely the film follows the book, and the film stands entirely on its own. You need know nothing about the novel, or about wine, to follow Miles and Jack.
What should I watch after Sideways?
After Sideways, try Withnail and I (1987, Fi1m 88): Another fraught holiday with difficult men whose company proves hard to relinquish. Then The Lunchbox (2013, Fi1m 75): For the tentative romance, patient observation and pleasure taken in ordinary meals; and Another Round (2020, Fi1m 80): Alcohol, male friendship and disappointment, with a more openly reckless appetite.

Cast

Awards

Academy Awards, 2005

Nominated
Best Director
Nominated
Best Picture
Nominated
Best Supporting Actor
Nominated
Best Supporting Actress
Won
Best Writing, Adapted Screenplay

If you liked this, try…

  1. Withnail and I (1987, Fi1m 88)Another fraught holiday with difficult men whose company proves hard to relinquish.

  2. Il sorpasso (1962) · not reviewed yetA mismatched pair take to the road, with charm and carelessness competing.

  3. The Lunchbox (2013, Fi1m 75)For the tentative romance, patient observation and pleasure taken in ordinary meals.

  4. Another Round (2020, Fi1m 80)Alcohol, male friendship and disappointment, with a more openly reckless appetite.

  5. The Station Agent (2003, Fi1m 82)A quieter study of prickly people finding friendship without becoming conveniently agreeable.

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