This Distracted Globe random header image

Sideways (2004)

May 21st, 2008 · 9 Comments

sideways-2004-poster.jpg   sideways-dvd-cover.jpg

Hung over from a wine tasting, Miles Raymond (Paul Giamatti) oversleeps and hits the road late from San Diego to L.A. to pick up his crass buddy Jack Lopate (Thomas Haden Church). Miles has finished a novel. Jack is an actor about to be married. To celebrate, Miles has planned a week in Santa Barbara County. “We’re gonna drink a lot of good wine, we’re gonna play some golf, we’re gonna eat some great food, we’re going to enjoy the scenery and we’re going to send you off in style, mon frere.”

After stopping for the night in Oxnard to visit Miles’ mother (Marylouise Burke) – and to steal some cash – Miles and Jack arrive in Buellton for dinner. A waitress named Maya (Virigina Madsen) recognizes Miles from his previous visits. Jack claims they’re in town to celebrate Miles’ book being published. Despite her attention, Miles acts uninterested in Maya. Jack reads his buddy the riot act: “I am going to get my nut on this trip, Miles, and you are not going to fuck it up for me with all your depression and anxiety and neg-head downer shit.”

On a grape tour, the men meet a bohemian winery employee named Stephanie (Sandra Oh). Miles dislikes the Cabernet Franc they sample, but Jack likes her service enough to arrange them a dinner date with her and Maya. Being back in Santa Ynez Valley reminds Miles of being there with his ex-wife, Victoria. Jack breaks the news that Victoria has remarried and will be attending the wedding with her new husband. Miles falls into a deep funk and before dinner, his friend has to remind him to behave. “I don’t want you passing out or going to the dark side.”


Miles is unable to resist stumbling to a phone and drunk dialing his ex-wife in despair. While the evening turns amorous between Jack and Stephanie, Miles is only able to express his feelings for Maya by talking about his love for Pinot. Jack neglects to mention to his latest conquest that he’s getting married, and ditches Miles to hang out with Stephanie and her daughter. While spending more time with Maya, Miles lets it slip that Jack is getting married. This results in some serious pain for Jack in the short term. Miles takes him home for the wedding, but is unable to get Maya out of his mind.

Production history
Rex Pickett had spent twenty years as a screenwriter and aspiring filmmaker. By 1998 he was divorced, nearly broke and ready to walk away from Hollywood. He tried remaking himself as a novelist and landed agents on both coasts, but fifteen different publishers rejected his first manuscript. Desperate, Pickett had one last idea for a novel. It was based on a road trip he’d taken to Santa Barbara County, “introducing my friend to wine and telling him all these crazy stories.” Pickett’s friend urged him to write about it.

Pickett based the self-loathing novelist and wine connoisseur Miles on himself and the self-possessed actor Jack on his own friend. His agent felt the manuscript read so much like a movie that he tried submitting to producers. Pickett passed a draft to producer Michael London, a college friend. London felt the material might interest writer-director Alexander Payne. “I knew he would like the idea of two guys who go to such an idyllic place on what should be a very happy trip only to find pain and misery as a result of their self-induced misadventures.”


Payne was busy promoting Election, but when he finally got around to reading Pickett’s manuscript in August 1999, “went nuts for it.” Already in pre-production on About Schmidt, Payne split the cost of an option on Sideways with London and committed to making it later. Adapting a spec screenplay with his collaborator Jim Taylor, Payne pooled $10,000 with a matching sum from London, opened an office, hired a casting director and started meeting actors.

George Clooney, Brad Pitt, John Cusack and Russell Crowe were among those who either loved the material or wanted to work with Payne, but through the audition process, the director was most impressed by Paul Giamatti and Thomas Haden Church. Virginia Madsen – who also made an impression on Payne with her reading – joined the director’s wife Sandra Oh as the female leads. Even with the opportunity for a bigger budget with bankable movie stars, Payne stuck with his cast.

Fox Searchlight liked the package enough to commit $16 million in financing and shooting commenced in September 2003. St. Martin’s published Pickett’s book the following spring, but considered its commercial potential so bleak that the author had to promote it out of his own pocket. The movie’s box office prospects seemed almost as dim, but when released October 2004, Sideways received nearly unanimous critical praise and five Academy Award nominations on its way to grossing a surprising $71 million in the U.S.


not only rocketed veteran actors Giamatti, Church and Madsen to the top of casting lists, it defied expectations by drawing audiences in spite of its unsympathetic male characters. Payne commented on the film’s appeal by stating, “Perhaps too many films in this current era have eschewed humanity for slickness. I’m interested in revitalizing the American cinema of the ‘70s with its emphasis on real people and real struggles, and I think we desperately need human movies right now.”


While the look and feel of the film has its foothold the ‘70s – particularly the work of Hal Ashby – the reason Sideways is a classic has everything to do with its commitment to its characters. When it comes to big screen hilarity witnessed in the ‘00s, two sequences in the last half hour rank at the top, but Payne & Taylor aren’t working for laughs or trying to make a hip comedy. Their screenplay explores the questionable decisions and bad taste of its characters with the sophistication and finesse only the best writing can summon.

The casting – which garnered Oscar nominations for Thomas Haden Church and Virginia Madsen, and cut Paul Giamatti loose in the most flammable role of his career – is an ingenious complement to Rex Pickett’s source material, which fluctuates between the exterior beauty of Santa Ynez Valley and the rancor of its central character’s inner life. Payne imbues the film with a tremendous sense of freedom, particularly in the jazz score by Rolfe Kent, which like everything else in the film, is pitch perfect.


Steve Evans at DVD Verdict writes, “Payne and his marvelous cast deliver a superb entertainment—intelligent, provocative, heartfelt, and funny as hell. No more observant a comedy about male-female relationships has been released in the last 25 years, which is as much a wistful observation as it is cause for celebration. Like a perfect Pinot Noir, Sideways hits the spot.”

“As much as Payne lampoons the haughty language of the tasting elite, he also uses wine as a natural metaphor for aging gracefully and seizing peak moments before they crest. Though his unpretentious style and generous sense of humor could be mistaken for a lack of artistry, Payne’s knack for broad, crowd-pleasing comedy fails to do justice to how much thought and feeling goes into the tiniest details in his movies,” writes Scott Tobias at The Onion A.V. Club.

Michelle Thomas at Future Movies Reviews writes, “Sideways will speak to anyone who has ever thought themselves a bit of a failure or gazed into the abyss between the mountain of their ambitions and the slag heap of their actual achievements … It’s also really refreshing to see women in a movie who are the right age to be with these men – both Oh and Madsen are extremely attractive, but they look real, they have wrinkles, they also have charm and stories to tell and a bit of life experience. Hurrah! Directors, take note.”

© Joe Valdez

Tags: Ambiguous ending · Based on novel · Black comedy · Drunk scene · Mother/son relationship · Road trip · Small town

9 responses so far ↓

  • 1 Joseph // May 21, 2008 at 7:09 pm

    Sideways is a gem of a film that I picked up for 50 cents at the library. It hit me on so many levels throughout the film. Great characters, especially contrasting characteristics between them.

    That scene that always gets me is the conversation between Paul Giamatti and Virginia Madsen outside during the double date. Over-the-top symbolic parallels, but I love it. :-)

  • 2 Chuck // May 22, 2008 at 9:24 am

    Sideways is one of the few modern movies that I’m comfortable calling one of my favorite movies (period). It’s warm, generous, human, and, while I love Payne’s work in general (excluding Citizen Ruth which I find overrated) Sideways represents major growth, particularly in spirit. Schmidt is tremendously moving (love that ending) but Payne cheats a little in the portrayal of many of the side characters, retreating into caricature. Sideways plays fair from start to finish, with four rich, off the path performances that refuse to highlight for the cheap seats. Favorite moments? Virtually every scene in the movie-but a major devastater is Miles’ ex-wife’s revelation that she’s pregnant-Giamatti’s face crumbles, briefly, swallowing the disappointment, and moves on. Or how about him drinking the wine in the burger place?

    The ending is even nearly as devastating a promise of hope amongst hopelessness as Schmidt’s, and tremendously earned. A masterpiece. Thank you for this coverage.

  • 3 Marilyn // May 24, 2008 at 10:25 am

    I have to admit that neither the hubby nor I liked Sideways. Yes, I know that yuppies—somewhere down there–are people, too. But neither of us could get away from the idea that this was just another one of their facile attempts at being real. I am glad it catapulted Paul Giamatti into a real career, but that’s about all I can say for it. Photographing Oh with her legs in the air was an unnecessarily humiliating way for Payne to deal with her character – no wonder they’re divorced now.

  • 4 AR // May 25, 2008 at 4:15 pm

    I personally found this film highly overrated, though I’ll grant that it had reasonably good dialogue and was altogether well made. It’s been a few years since I’ve seen it, so I’d need to refresh my memory regarding the details as to why.

  • 5 Joe Valdez // May 25, 2008 at 7:28 pm

    Joseph: The drunk dialing of the ex-wife was my favorite scene. It’s so easy to imagine the bad version of that scene in some dumb romantic comedy. Here was a movie that instead of going to the audience, asked the audience come to it, if that makes sense.

    Chuck: I think you have to credit Rex Pickett. As a guy, I have gone through my occasional Miles moment I’m not happy to say – like the encounter with the ex – but it’s so rare you see that captured in fiction in a believable way. I can’t believe I still haven’t seen About Schmidt. Thanks for giving me another rental idea and for commenting!

    Marilyn: I didn’t get the sense this movie had anything to do with Yuppies. Neither Miles or Jack are exactly young and they’re certainly not professionals; they’re pretty much losers in their careers and life. I’m surprised you felt there was a chauvinist slant here. I thought the female characters were imbued with a genuine voice and strength and one of the female reviewers I mention did as well.

    AR: Yeah, I think maybe if you substitute “wine” with “film” a lot of critics could see themselves as Miles, particularly in the looks department. This could be one reason why all the reviews were so positive. However, I don’t know how many other recent comedies you could say were better than this one. Lost In Translation? Wedding Crashers? Those to me were vastly overrated.

  • 6 Marilyn // May 26, 2008 at 11:04 am

    Yuppie isn’t exactly a demographic to me–it’s a state of mind. Madsen certainly played a well-fleshed character, but I felt like Payne was making Oh into a caricature, particularly with her bashing Haden-Church with her helmet. Damn, she almost killed him! There was trouble in the Payne/Oh marriage that made its way to the screen.

    Oh, and has Madsen had another great role since then? Sexism in the industry cancels out sexism on the screen in this case, though that’s not the fault of the movie, of course.

  • 7 AR // May 27, 2008 at 2:26 pm

    Lost in Translation is a comedy? I thought it was a drama, but I liked it more than Sideways.
    Wedding Crashers, no comment. Haven’t seen it, not desperate to see it any time soon.
    The only recent comedy I’ve seen that I’ve really deeply liked is The 40 Year Old Virgin. Does that make it better? I’m not sure. I think I could say that Sideways is more obviously well crafted and thoughtful.

    Recalling some of my issues, while I choose not to speculate about Payne and Oh’s relationship, I did find Oh’s reaction cliched and awfully hasty for one night’s worth of romance. Was the characterization of the chubby waitress and her cuckolded husband really that deep? The resolution with Madsen’s character leaving that message…I dunno if that really worked for me.
    I do think the critics lavished praise for the reasons laid out by Payne. It’s not a slick movie, it takes its time, it focuses more on characters than action. That sort of thing is such a rarity these days that when people see it they sometimes get over-zealous in their excitement.

  • 8 Daniel // May 27, 2008 at 3:19 pm

    I like Sideways more and more with each viewing. I really can’t relate to any of the characters, but it’s enough just to watch Giamatti and Haden Church together. Any other casting choice may have sunk this gem.

  • 9 Pat Evans // May 29, 2008 at 10:20 pm

    This is one great little movie which will live on as a cult favorite for many viewers, while others will remain impervious to its charms. Small, character-driven films are not for everyone — nor should they be.

Leave a Comment