“Sideways” follows two bachelors in their early forties who head north from San Diego on a road trip to Santa Barbara County wine country. Miles (Paul Giamatti) is a down-and-out schoolteacher trying to get his novel published. Jack (Thomas Haden Church) is an actor about to be married to a young and beautiful Armenian woman, and he and Miles hit the road for a bachelor getaway the week before the wedding.
Miles and Jack couldn’t be more different, but they roomed together as freshman at San Diego State. Many of us can relate to this type of friendship forged more through circumstance than having anything in common. But the bonds we form at that age are real, even if we’re very different people.
Miles is a glass-half-empty sort of guy, and Jack makes it clear early on that he’s not going to put up with his negativity on the trip. Not that Miles doesn’t have reasons to be a bit depressed. His marriage fell apart, and he still pines for his ex-wife. He’s also struggling to get his book published. Jack is a happy-go-lucky hedonist, and he just wants to relax and get laid on this trip. And he wants Miles to get laid. What are friends for?
Miles is also a wine snob, and much of the movie revolves around introducing the audience to wine culture and the beautiful wine country around Santa Barbara. Miles loves Pinot Noir, but hilariously hates Merlot. The film was so influential that it boosted production and sales of Pinot Noir and depressed Merlot sales. If you visit Santa Barbara County wine country now, you’ll find plenty of tours based on the film.
We meet Maya (Virginia Madsen) and Stephanie (Sandra Oh) early in the film, and the story revolves around the relationships that develop among these characters. Maya is a waitress at The Hitching Post where ethe guys are having dinner, and Jack notices that Maya is into Miles, who naturally is oblivious. Stephanie works at one of the wineries, and Jack wastes no time hitting on her. Jack and sexy Stephanie have instant chemistry, while Miles battles his internal demons as he awkwardly tries to engage with lovely Maya.
There’s so much to love about this film. It’s often hilarious, and most guys will appreciate how old friends Miles and Jack argue and rip on one another. But there’s a genuine bond between them as well which is tested through the twists and turns of their adventure.
The four lead actors deliver brilliant performances, with Haden Church and Madsen earning Best Supporting Actor and Actress nominations. Giamatti and Oh also deserved nominations. The film also garnered nominations for Best Picture and Best Director (Alexander Payne) while winning the Oscar for Best Adapted Screenplay. (Watch the trailer here)
So grab a nice bottle of Pinot Noir and check this one out if you haven’t done so, or just enjoy it again. It’s a timeless classic.