Monday, July 15, 2024


THE STORY – Struggling writer and wine enthusiast Miles takes his engaged friend, Jack, on a trip to wine country for a last single-guy bonding experience. While Miles wants to relax and enjoy the wine, Jack is in search of a fling before his wedding. Soon Jack is sleeping with Stephanie, while her friend Maya connects with Miles. When Miles lets slip that Jack is getting married, both women are furious, sending the trip into disarray.

THE CAST – Paul Giamatti, Thomas Hayden Church, Virginia Madsen & Sandra Oh

THE TEAM – Alexander Payne (Director/Writer) & Jim Taylor (Writer)

THE RUNNING TIME – 127 Minutes

Alexander Payne’s ability to render characters lovable despite their flaws was evident from his first film. He understands that a character’s flaws are what make them lovable in the first place. An audience member will forgive a lot if they feel the character being depicted onscreen has made a mistake that they, too, have made or would have made in a similar situation. We can’t help but root for someone who shares in our misery, even if their misery is filtered through snappy dialogue and utterly charming performers.

All of Payne’s films scratch the itch of the awkwardly, painfully funny, but “Sideways” remains, for many, his magnum opus. It was a surprise box office success upon its release in 2004, and it earned five Oscar nominations, winning Best Adapted Screenplay for Payne and Jim Taylor. It remains the quintessential film about wine, even though the wine is merely an excuse for the characters to express things about themselves they would otherwise be unable to. I’m pleased to report that “Sideways” holds up after nearly two decades. It may be even better now.

“Sideways” revolves around Miles Raymond (Paul Giamatti) and Jack (Thomas Hayden Church), longtime buddies who take a trip to Santa Barbara to celebrate the latter’s upcoming wedding. Miles is a wine connoisseur and aspiring writer eager to taste his way through Santa Ynez Valley, and Jack is a former TV star looking to sow his wild oats before he settles down. Both men find what they’re looking for when they encounter Maya (Virginia Madsen) and Stephanie (Sandra Oh), two Santa Ynez employees. However, Miles’ neurosis, coupled with Jack’s obliviousness, brings about complications.

Complications may be underselling it. “Sideways” may have the trappings of an indie drama, but it delights in puncturing this quant aesthetic with outlandish moments of physical comedy and embarrassing outbursts. Jack takes a motorcycle helmet to the face when it’s discovered that he has a fiance and spends a decent chunk of the film with a “Chinatown”-sized bandage on his nose. Miles has to sneak into a local couple’s house to retrieve Jack’s wallet, and proceeds to be chased by a man in the buff. Payne’s directorial heroes, Hal Ashby and Mike Nichols understood the impact that a few moments of absurdity could have in an otherwise realistic setting, and he implemented them in such a way that they still managed to elicit shocked laughter after a dozen viewings.

The thing that allows these absurd moments to work, of course, is the perfectly calibrated screenplay. Payne and Taylor adapt Rex Pickett’s 2004 novel of the same name and manage the rare feat of making each character feel three-dimensional regardless of the amount of screen time they’re given. Maya and Stephanie are fleeting presences compared to the main duo, and yet, the few moments they have illuminate who they are, how they got here, and why they go on to behave the way they do when they discover their new friends may be full of it. The scene in which Miles and Maya discuss wine preferences is the best example of this and the one that likely solidified a Best Supporting Actress nomination for Virginia Madsen.

The scene is initially framed around Miles, who delivers a monologue about the virtues of Pinot Noir, inadvertently describing himself in the process. It’s a gorgeous piece of writing, and Giamatti nails the tonal balance of being flustered by Maya’s presence but eager to share his thoughts with someone who actually knows their wine. The film takes a beat, then proceeds to shift the focus to Maya, who describes her experiences with wine and the ways in which it informs her overall outlook on life. Stacking a monologue on top of another monologue rarely works, yet the delicate, non-flashy writing turns a simple exchange into the film’s emotional centerpiece. If this were the only sequence to feature Miles and Maya, we would still have an innate understanding of them as people.

Of course, a near-perfect screenplay would fall short without a stellar cast. Giamatti, Church, and Madsen had established screen personas by the time they appeared in “Sideways,” and part of what makes their performances such a revelation is the way the film tweaks and deepens these personas. Church and Madsen spent the 1990s playing the comic relief and the femme fatale, which the screenplay wisely calls upon through allusions to their characters’ past. Still, it knows when to zig and present the viewer with a vulnerable, sobbing Jack or a Maya who’d been on the receiving end of a bad relationship. Sandra Oh gets the least characterization to play with, which makes up the screenplay’s lone failing, yet the actress manages to steal most of her scenes through sheer presence.

Giamatti gives the performance of his career. He was already one of Hollywood’s most reliable supporting actors when he was cast as Miles, and the character meshed perfectly with his unique combination of vulnerability and barely masked frustration. Miles is loathsome in the wrong hands, or unbelievable if George Clooney had gotten his way and been cast (Payne wisely repurposed Clooney for “The Descendants“). He lies in the film’s first five minutes, is openly selfish, and is ultimately so self-pitying that he causes a scene upon learning that his long-gestating novel has been rejected for publication. Giamatti’s expressive eyes ensure that we are on his side for the entirety of the film’s 127-minute runtime. Few actors are better at making us see ourselves in their struggles.

“Sideways” has some dated elements, including the blown-out cinematography by Phedon Papamichael and the lounge music score, but the film’s construction is so sound that these elements have become charming rather than distracting. The direction, performances, and writing are evergreen examples of what can be achieved within an intimate framework and remain high water marks for nearly everyone involved. “Sideways” is the kind of film “they don’t make anymore,” but if we’re being truthful, they rarely ever made them this good.


THE GOOD - The screenplay is one of the finest of the 21st century, while Giamatti, Church, and Madsen give the performances of their respective careers.

THE BAD - The lack of characterization for Stephanie stands out next to the other characters, and some of the film's aesthetic choices now play as dated.



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Danilo Castro
Danilo Castro
Music lover. Writer for Screen Rant, Noir Foundation, Classic Movie Hub & Little White Lies.

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Latest Reviews

<b>THE GOOD - </b>The screenplay is one of the finest of the 21st century, while Giamatti, Church, and Madsen give the performances of their respective careers.<br><br> <b>THE BAD - </b>The lack of characterization for Stephanie stands out next to the other characters, and some of the film's aesthetic choices now play as dated.<br><br> <b>THE OSCARS - </b>None <br><br> <b>THE FINAL SCORE - </b>9/10<br><br>"SIDEWAYS"