2004 / Best Director / Best Picture / Best Supporting Actor / Best Supporting Actress

Film #425: Sideways (2004)

So far of all the Best Picture Winners and nominees from the 21st century, only one has been set in the present day with all the others occurring either in the past or in a different realm altogether. I hope to redress this balance with the next three films on the list, all of which take place in present day America and feature quirky characters and bizarre premises. All three are archetypal examples of what has become to be known as ‘indie comedy’ films that don’t feature big stars and are on the whole quite funny. All three impressed Oscar enough to garner a Best Picture nomination with their respective screenplays all garnering Academy Awards in the writing categories.

The first film in this unofficial trilogy is Sideways; director Alexander Payne’s adaptation of Rex Pickett’s book of the same name. The film follows former college roommates Miles and Jack as they journey to the San Fernando Wine Valley to celebrate the upcoming wedding of the latter. One of the best things about Sideways is the way in which it makes you care about two characters who aren’t necessarily the most likeable of guys. For example an early scene sees Miles rock up at his mum’s house with the sole intent of eating her food and stealing money from her bedroom. Meanwhile Jack’s main intention of getting away from Christine seems to be so he can get his end away one last time. He does this quite quickly when he meets vineyard employee and single mother Stephanie; with the two participating in a whirlwind romance during the week over which the film is set. Meanwhile Jack tries to set up Miles with Maya; a prior acquaintance who works as a waitress at the local restaurant. As the week progresses, Jack leaves Miles on his own whilst he continues a relationship with Stephanie with it eventually ending abruptly after the predictable revelation of the upcoming wedding. Like all three films in this list, it was hard to guess just in what direction Sideways was heading and that’s possibly one of its greatest strengths. Although I felt that Miles and Maya may hook up, things get muddied after she finds out about Jack’s wedding and the reason the pair were in the wine valley in the first place.

It’s been a while since I watched Sideways, although it’s a film that I remember liking immensely when I first saw it. That feeling remained upon this most recent viewing and I feel like the film really deserved all of the Oscar nominations it got. Payne’s win for Best Adapted Screenplay, which he shared with co-writer Jim Taylor, was an especially worthy win seeing as the script is one of Sideways’ greatest attributes. Although I couldn’t remember the film entirely, Maya’s speech about why she loves wine has stuck with me over the past decade whilst some of the more comedic segments are equally well crafted. As Maya, Virginia Masden was awarded with a nomination in the Best Supporting Actress category, which I felt was more than deserved due to her measured and tender performance throughout the film. Thomas Hayden Church’s madcap turn as Jack also saw him pop up in the supporting actor category and I found his performance to be the perfect balance of seriousness and slapstick. One glaring omission was Paul Giamatti’s lead actor nod because, as Miles, I thought he was terrific; giving an engaging performance as a miserable middle-aged man who realised that he’d never achieve greatness. The academy realised their mistake by giving Giamatti a nomination the next year for playing Russell Crowe’s boxing trainer in Cinderella Man. However, Sideways remains his most accomplished performance to date and it’s a shame that Oscar didn’t spot this at the time. Rolfe Kent’s jazz-infused score and Phedon Papamichael’s excellent shooting of the Californian wine region were other brilliant elements of this excellent film. Sideways main achievement though was to put Alexander Payne on the map, with his next two films also garnering Best Picture nods. Overall, Sideways was a witty and wry look at middle-age with a fantastic script and a quartet of fantastic excellent central performances.


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