No. 45: “Sideways” (2005)

“Only somebody who really takes the time to understand Pinot’s potential can then coax it into its fullest expression.”
~~Miles Raymond

Alcoholism has many faces in film — Tommy Basilio (“Trees Lounge”), Dixon Steele (“In a Lonely Place”), Joe Clay (“Days of Wine and Roses”), George and Martha “(“Who’s Afraid of Virginia Woolf?”), to name a few. Alexander Payne’s sharp, touching “Sideways” makes a strong case for adding failed novelist Miles Raymond (Paul Giamatti) to that list. He can stagger along with these boozers; actually, he could put them to shame with his frightful pretentiousness. He’s too busy appraising wines as “quaffable but far from transcendent” to consider that he’s tasting his liver to an early grave.

“Sideways” has a bit of fun at the expense of self-appointed sommeliers like Miles. On paper, he is unappealing: aloof, condescending, persnickety to the nth degree. Miles steals cash from his mother’s underwear drawer. He is that dinner party guest who will march right out the door — hurling insults all the way — if he spies one bottle of merlot in the wine rack. Giamatti has played such men before, so he knows how to suggest the painful vulnerability underneath all the snobbishness. The humanity sneaks out in the little moments, like Miles’ drunk phone call to his ex-wife (Jessica Hecht), or his sadly beautiful speech about Pinot (really a veiled description of his own neuroses and nuances). It becomes more evident, too, the more time he spends with his slick, womanizing old college roommate Jack (Thomas Haden Church). The duo jaunts out to Santa Barbara County wine country for Jack’s bachelor party weekend, which Miles tolerates mostly because there will be wine, and lots of it. Otherwise, these two would have nothing to hold their friendship together but a few years of communal showers and keggers. It’s an Oscar-and-Felix partnership that’s long past its expiration date. But Church and Giamatti are a formidable comedic duo.

Jack’s libido is the cause of many of the hijinks in “Sideways,” most involving slapstick, plenty of enthusiastic sex and nudity. Out to sew his wild oats while the sewing’s good, Jack ends up romancing Stephanie (Sandra Oh), who works at a local winery. That leaves Miles to play the part of the wingman. He doesn’t grumble about that because he’s been quietly in love with Maya (Virginia Madsen), Stephanie’s friend, for years. Giamatti communicates this wonderfully in several scenes, particularly one late night when Maya drives Miles home. As she watches the road, the normally timid Miles gives himself permission to look at her, really look at her. Giamatti’s face and eyes are so revealing that dialogue is superfluous. Rare is the actor who can say everything with a lingering look. Bogart accomplished this feat in “Key Largo”; here, Giamatti matches him. This kind of talent doesn’t come along every day.

“Sideways,” based on Rex Pickett’s novel, might well be a full-blown character study if not for the comedy the Church/Giamatti pairing provides. Their differences are never more obvious, or hilarious, than when Miles tries to teach Jack the art of wine tasting. Jack’s more of a fill-my-glass-to-the-top kind of taster with no nose for subtleties. He’s an actor who’s accustomed to instant gratification, so when he decides he wants to ditch his gorgeous, rich fiancée (Alysia Reiner) and live with Stephanie, he can’t understand why Miles thinks it’s a bonehead move. “Sideways” is jam-packed with those kinds of stupid choices, the funniest being Jack’s dalliance with a waitress that sends him running naked back to the hotel when her husband gets home. Church has a grand ole’ time playing the vapid pretty boy (Church is a good enough actor that he bends our sympathy to Jack) to Giamatti’s oversensitive, smug overthinker. The Giamatti/Madsen pairing fairs even better, with Madsen hitting a career high as the intuitive Maya. Her careful response to Miles’ speech on the merits of Pinot marks one of the film’s most honest moments. For all the comedy, this is what we take away from “Sideways”: that there are people out there willing to coax us to our fullest expression. And when we meet then, we’d better hold on tight.

11 Responses

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  2. The quote at the top is one of my favourite lines! Another quote I love is “did you drink n dial, Miles” ( :

    The way Miles and Jack both encourage and stand by one another even at their lowest moments is the heart of the movie for me, for example the golf scene, or the smudge on a skyscraper dialogue. I think they realize on the trip this is what their friendship is about- support. So I think “coax us to our fullest expression” also is between miles and jack in some ways, do you agree?

    You may have noticed I also reviewed Sideways recently

  3. i have a huge crush on virginia madsen, hmmmmmmmmmm

  4. LOVE LOVE LOVE this movie. The poster is framed in my bedroom. Partly cuz it’s good and partly cuz it’s about booze… yes, wine counts! :)

    • @ Chris — You know, I’d never thought of Miles and Jack’s friendship that way, but you make a great point. In the past I’ve mostly wondered “What the hell do these guys have in common anymore?” I can see how maybe their friendship does deepen because of what happens on the trip.

      @ Japan — This movie was filmed before she had some awful work done, which is evident in the equally awful “Red Riding Hood.” Such a pity — she was a natural beauty for sure.

      @ Kaiderman — Wine is wimpy booze, but I’ll take it when nothing else is around!

  5. This is such a great film! I need to revisit it real soon. Love when he chugs the wine at the arbys/wendys place.

    • I think that’s one of the most poignant moments in the film. It’s sad, but it’s also kind of hopeful and it shows us how much Miles has changed — before that weekend, he’d NEVER drink his prized wine at all, much less out of a styrofoam cup!

  6. I absolutely adore this film and at the time it came out, I was big into wine tastings with friends – so there was an added level of personal hilarity for us. Great fun, and thoughtful review as always!

    • Thanks, Klaus — I like to hear from other people who love “Sideways” because they offer different perspectives. For example, I never considered how Miles and Jack’s friendship is “coaxed to its fullest expression.” I also tend to downplay the comedy because I enjoy Miles and Maya’s tentative romance so much. But “Sideways,” like all great films, shows me something new and different and wonderful every time I see it.

  7. I think my alcoholism is why I love the film so much.

  8. I just watched this again a few weeks ago. Like wine, it has gotten better with age. I didn’t not like it the first few times. Now, not so bad.

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