Life is full of sweet highs and terrible merlots on today’s Script Apart as Alexander Payne – director of movies like Election, The Holdovers, Nebraska and About Schmidt – joins us to raise a glass to an indie drama that has aged like a fine wine. The brilliant Sideways was released in 2004 and soon earned four Academy Award nominations, taking home Best Adapted Screenplay. It won six Independent Spirit Awards, was picked up for Japanese remake and instigated a huge tourism boom in the California wine country that forms the film’s backdrop. Co-written with frequent collaborator Jim Taylor, it told the tale of two friends on a wine tasting expedition,  each struggling to break out of a certain middle-aged, middle-class male malaise (one of Alexander’s screenwriting specialties). The result? A dramedy widely regarded as one of the best of its decade.

The film saw Paul Giamatti play Miles – an aspiring author whose dreams of literary stardom are misfiring, much like his love life. Recently divorced, he and his old college friend Jack, played by Thomas Haden Church, hop in the car to celebrate Jack’s upcoming wedding. But Jack – a washed-up soap opera actor – is intent on hooking up with women as part of one last sexual hurrah before marriage. Caught up in the mix as the pair quarrel and cause trouble is Virginia Madsen’s Maya, a barmaid that Miles strikes up feelings for. Professing those feelings in a serious way, though, is difficult for the wine aficionado and English teacher – a man so mired in regret about what was, he’s unable to grasp the now and what could still be. 

Much is often made about the recurring quote-unquote “losers” that lead Alexander’s films, and what they might have to say about modern American man. The filmmaker, though, has always been pretty resolute that his movies centre the downtrodden and dopey simply because, deep down, these films are comedies – a genre the historically sides with the little guy, going all the way back to Charlie Chaplin. But how does he define the mix of pathos and hilarity that fill his characters? Where does Alexander’s affinity towards road trip stories come from?  What’s so relatable and real about Miles’ fear that his literary dreams might amount to nothing – and that a life of feeling like a loser awaits? And what was the inspiration behind the film’s beautiful ending – a knock at the door that we as an audience never see answered? All is revealed across a fascinating thirty-minute sit down with the auteuer.

Script Apart is hosted by Al Horner and produced by Kamil Dymek. Follow us on Instagram, or email us on thescriptapartpodcast@gmail.com.

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