“A wine tasting road trip to salute a bachelor’s final days careens woefully sideways as he and his buddy hit the gas en route to mid-life crises.”
The story follows two friends, Miles (Paul Giamatti), a depressed, struggling writer, and Jack (Thomas Haden Church), a washed-up actor on the brink of marriage, as they embark on a week-long trip through Santa Barbara’s wine country. What begins as a bachelor getaway quickly turns into a journey of self-discovery. Miles, a wine aficionado, hopes to drown his insecurities in Pinot Noir, while Jack is determined to have one last fling before settling down. Along the way, they meet two women: Maya (Virginia Madsen), a kind-hearted waitress who shares Miles’ love for wine, and Stephanie (Sandra Oh), a fiery woman whose fling with Jack complicates everything.
Alexander Payne delivers a poignant film that I still enjoy after all these years. Filled with smart and witty humor that certainly won’t land with every filmgoer out there, as funny as it is, it’s also heartbreaking on many levels. The Miles character especially is perhaps one of the most nuanced and layered characters I’ve seen, with his depression caused by his divorce two years ago, also fueled by constant rejection of his novel he’s poured his heart and soul into, and the consistent reminder of the failures in his life. Even if you don’t enjoy the subject matter of wine, that could honestly be about anything and still present a fantastic character-driven story that will leave a lasting emotional impact. Despite Miles’ awkward interactions throughout, his longing for connection drives the themes of the film.
Paul Giamatti delivers probably his best performance of his career. The depression and vulnerability he experiences throughout his road trip seems authentic, as is the crushing devastation when certain information is presented to him that deeply affects him. Despite everything he has going on in his own life, his desire to give his best friend a fun-filled trip of wine tasting and exploration of Northern California also demonstrates the chemistry that he and Thomas Hayden Church have in the film. Their back-and-forth banter, with Jack’s almost insultingly poor knowledge of wine and tasting practices make for a lot of the comedy in the film, but it’s the friendship between them demonstrated in some of the more tense sequences such as Miles retrieving Jack’s wallet that show just how much these actors make us believe they’ve been life-long friends.
Perhaps it’s that I’m a bit older since I saw Sideways, and I hate to do such an obvious pun, but the film really has aged like fine wine. It certainly is a film that you connect more to as you get older, as you experience defeats in your life, or it hasn’t gone exactly as you’ve planned. The film promotes finding the smaller victories, as happiness can be somewhat fleeting.
We were given a digital code to review, which is now available in 4k for the first time at digital retailers (Prime Video, Apple TV, and Fandango). Being the 20th anniversary, the 4k release digitally was a nice surprise. Since 20th Century Fox is now owned by Disney, it’s unlikely we’ll get a physical 4k release, but there is always hope. The 4k digital version of this film is available now.