The 365 Best Films of the 2000s

Heroes of the Zeroes: Sideways

Heroes of the Zeroes is Nick Rogers’ daily, alphabetical look back at the 365 best films of 2000-2009.

Rated R

Paul Giamatti’s stack-blowing skill borders on the supernatural. Lips quiver, eyes dart for an escape he’ll never find and his jittery voice cracks until his patience evaporates in a profane eruption.

When it came to hitting the ceiling, Miles Raymond of 2004’s “Sideways” represented Giamatti’s Sistine Chapel — a divorced, flabby, middle-aged English teacher able to discern when “Barely Legal” isn’t “the new issue” and whose fine-wine enthusiasm masks borderline alcoholism.

A natural fit for a romantic comedy — or at least one from co-writer/director Alexander Payne, fascinated by the emotional muck of people past their prime.

Miles and actor pal Jack (Thomas Haden Church, never better) drive to California wine country for a weeklong getaway before Jack’s wedding. There, Miles finally pursues Maya (Virginia Madsen), a waitress he’s fancied, as Jack foolishly sleeps with her single-mom friend, Stephanie (Sandra Oh).

“Sideways” is about wine aged to perfection sipped by men who’ve aged to mediocrity — softer, hornier versions of Walter and The Dude. But Miles’s brutal honesty is its soul. He’s annoyingly, depressingly out there, but never fraudulent — unlike Jack, whose foolhardy libido incites comic scenarios both riotously funny and unexpectedly grotesque.

In other hands, wine-as-life metaphors might feel as refined as Mad Dog 20/20. But Giamatti and Madsen’s expressions, cadences and pauses possess that warm rush of realized love. Miles and Maya could go everywhere or nowhere, but she’s as close to peace as Miles will get. For somebody so low for so long, plateaus might as well be peaks.

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12 Responses to “Heroes of the Zeroes: Sideways”

  1. […] it could have been addressed more explicitly. In terms of Alexander Payne’s other films, “Sideways” is a more direct address of a cliche, commenting on Peter Pan syndrome through Thomas Haden […]

  2. […] Descendants” — Alexander Payne (“Sideways”) seems to be making films on a Kubrickian timetable, but this black comedy starring George Clooney […]

  3. […] “The Descendants” (11/23) — Alexander Payne (“Sideways”) directs this tragicomedy about a father (George Clooney) whose family always came second, until […]

  4. Joe Shearer says:

    Thanks for your comment, Michael, but I have to disagree a little on the ending. It wasn’t a happy ending; it was merely a hopeful one. That it ended with him knocking on the door and not actually coming face to face with Maya is vague at best. For all we know, she didn’t open the door, or opened the door, looked at him and slammed the door in his face. More likely she did, and they had some relationship, but what kind? Maybe just a friendly one, maybe it didn’t last. There are just too many things that could have happened.

    But it’s that hope that Miles needs more than anything. That’s what he lost and was really looking for throughout the movie, and he didn’t find happiness, just that little spark that can keep him going.

  5. Michael England says:

    I really enjoyed this film (as we call such entertainment in the UK!) and it was really good to see an American film displaying a degree of subtlety.

    But I was disappointed by the achingly predictable happy ending. I realise the commercial pressures from producers may make this inevitable, but in real life guys like this don’t always get happy endings, and it would have been a lot more courageous (& I’d have respected the fim a lot more) if they had simply finished the film without the voicemail message from Mia.

  6. Peter Kohn says:

    A trivia note — in Sideways, Virginia Madsen’s Maya plays opposite Paul Giamatti’s Miles. In Electric Dreams, she appeared opposite Lenny Von Dohlen also playing a character named Miles.

  7. jake says:

    ‘Mostly I enjoyed it though for the beautiful scenery in Napa Valley."

    It wasn’t filmed in Napa Valley (north of SF). It was filmed in the santa ynez valley (south of SF).

  8. Linda says:

    My brother talked me into seeing this movie when I was visiting him in California when it first came out. I was pleasantly surprised and enjoyed the movie more the second time I saw it. A couple of years later I actually went to the towns "Solvang, CA and Buellton, CA" where they shot the movie and got a few pictures under the sign of the restaurant where Virginia Madsen worked in the movie. I was thrilled but nobody ever appreciated my pictures because "Sideways" was a movie that alot of people had never seen. I would tell them they had to see it. This movie definitely did alot for the careers of Paul, Thomas, Virginia & Sandra.

  9. Nick Rogers says:

    mia: Like Joe, I can’t really see George Clooney in that role. At least not *good* George Clooney. I’ve not particularly cared for any of the three films he’s done with the Coen Brothers. A lot of times, Clooney confuses bugging his eyes out for comedy, and I fear he might have made Jack too much of a goofball.

    Joe: I will cop to a guilty-pleasure appreciation of "The Wedding Date," but I would never suggest its superiority to "Sideways."

    Sheryl: Of the four, Sandra Oh definitely has the most under-written role. (Perhaps that’s why she and Payne eventually split up.) And props for the mid-80s Virginia Madsen references. "Electric Dreams" is a great movie, and I remember the scene of the helicopter’s lights shining on the ridge from "Fire with Fire’s" heavy Showtime rotation. Thanks for reading!

  10. Sheryl Messersmith says:

    I saw this movie on my birthday when it first came out. I did enjoy it but it wouldn’t be one that I’d watch over and over – though I wouldn’t mind seeing it again sometime. Mostly I enjoyed it though for the beautiful scenery in Napa Valley. Sandra Oh was annoying to me, as she usually is, but I do love Thomas Hayden Church and also Virginia Madsen who I’ve been a fan of since I saw her in Electric Dreams (fun movie with great music) and Fire with Fire in the mid 80’s.

  11. Joe Shearer says:

    Interesting tidbit about Clooney. I’m trying to picture him as Jack saying "You need to get your JOINT worked on." Can’t imagine it being delivered the same way. THC was spot-perfect in that role.

    And also "Sideways" is one of my favorite movies as well.

    Let me tell you that in 5 years of going to advance screenings I’ve put up with people kicking my seat, talking loudly, munching snacks loudly, yelling at each other, and even fondling my leg, but the closest I ever came to punching someone was when I was leaving a screening of the Debra Messing movie "The Wedding Date" and the early-20-something girl behind me said "that was SO better than Sideways."

  12. One of my all-time favorite films. I could watch it over and over (and I have!).

    The last shot just kills me. So much hope.

    And what a fantastic cast. Rumor has it that George Clooney was interested in the role of Jack. While I like Clooney, I LOVED Thomas Haden Church.