20 years later, 'Sideways' remains a vintage film

Paul Giamatti deserved all the awards for his performance and got most of them.

If the appreciation of Paul Giamatti’s acting and I had a first date, it was Alexander Payne’s wickedly sharp Sideways. The movie, released twenty years ago, was sharp in its way of combining terrific acting, a superb script, and direction that said as much about human connection as it did wine. By the end, when Giamatti’s Miles knocks on Virginia Madsen’s door for a mulligan of sorts, you want more. More time with them and in a good way.

Payne’s film was nominated for several awards, including an Academy Award for Thomas Haden Church’s performance as Jack, Miles’ longtime friend who wants one last wild trip through wine country before he ties the knot. Church was great, but it was Giamatti who deserved all the accolades. He lived, breathed, and drank Miles for two hours. In real life, the actor didn’t know about or could care less about wine. He sure had me convinced.

Only wine savants or incredible actors say a line like “We’re not drinking any fucking Merlot,” and make you actually feel it. Built like a younger version of the eccentric professor in last year’s stellar Payne entry, The Holdovers, Miles carries the weight of all that has gone wrong in his life on his shoulders. Giamatti walks like his shoulders are being pinned to the surface by a failed marriage, an unpublished book, and a friend that is way more annoying than he was back in college.

He took you outside of the “oh, that’s just an actor” mindset for a viewer. You could have told me the film was based on the actor’s life and I would have bought it. Before he was the powerful Chuck on Showtime’s Billions or a true Bard man like Paul Hunnam, Giamatti showed up with Sideways. After seemingly every awards group nominated him for Best Actor, the Academy voters turned their collective heads. It’s further proof of how much they miss.

Sideways continues to age like a fine Pinot Noir, a highly sophisticated and hard-to-grow grape that Miles informs Jack and others about in the film. These kinds of golden indies, the ones that resemble a warm blanket, can’t be grown as easily either… especially these days where sequels and remakes own the lot. Payne’s film says a lot without being preachy or manipulative. How a connection between two humans can suddenly vanquish the uneasiness of previous romantic failures.

Madsen and Sandra Oh are great as the women who come into Miles and Jack’s world, upending it in good and bad ways. They match the realism of Payne’s writing to a tee. Before she was a fixture on Grey’s Anatomy, Oh was a heavy-pouring, free-spirited force of nature who whacked Church in the nose with a motorcycle helmet. Madsen’s sweet resolve pumps air into Miles’ cynical and morose perspective. She was nominated for a supporting Oscar, and it was a deserved selection.

If only Giamatti could have gotten the same love. My favorite scene in the film is an emotionally flattened Miles chowing down on a burger and fries while he pours a vintage bottle of wine into a Styrofoam cup. A hollow body dressed in a tux who just learned something that crushed him, it all felt natural due to Giamatti.

All of Sideways felt natural. It still does. Equal parts honest and hopeful about the daily struggles of adulting, it’s only gotten better with a couple decades under its belt.

It is currently streaming on Hulu.