Director: Alexander Payne | Runtime: 2h 7mins | Comedy, Drama
Adapted from the novel of the same name, Sideways follows the melancholic Miles Raymond (Paul Giamatti) as he takes his soon to be married close friend Jack Cole (Thomas Haden Church) on a trip round the vineyards of California. Whilst Miles aims to teach the groom-to-be about the elegance of wine, Jack intentions are far more centred around one last bachelor trip before tying the knot.
Alexander Payne has some truly great films under his directorial and writing belt, going back to 1999 for Election, 2011’s The Descendants and just directing 2013’s Nebraska show the talent he has as an artist. Although his most recent foray in Downsizing (2017) was certainly a miss, none of this are quite as striking as the Oscar winning Sideways. Picking up the award for adapted screenplay, it’s not just the writing that makes this piece one of the highest points in Payne’s career.
Completing the script with long time co-writer Jim Taylor they crafted two excellent opposites in Miles and Jack. Friends since living together in college, it’s hard to immediately see why they are friends; Jack is the good-looking actor and womanizer, whilst the divorced teacher in Miles lingers on a woman who’s long since left him behind. Although he seems successful on first appearance, Jack is well passed his career prime and is more clinging onto his previous successes than celebrating any new. Miles, on the other hand, has an incredible knowledge of wine but drinks so much that he is ever spiralling. Digging down to the roots of the leads shows how comparable they really are, and the weaknesses they lie at their cores. Although their motives differ the growth they both must go through to be happy is heartbreaking but necessary, and boils down to simple truths of understanding and appreciating themselves and those around them.
You may think that all this makes the pair unlikeable, but one of best crafted elements by Payne and Taylor is how relatable and sympathetic these really are – especially Giamatti. In the undoubtably best scene of the entire film being between Miles and Maya (who we will talk more about in a moment) as they discuss the merits and qualities of a Pinot Noir, with some beautiful nuance, but obvious enough for everyone to understand. Its a fine balance between being handed all the information and making it too subtle, but here the dialogue is written perfectly with flawless delivery and wonderfully paced direction – you couldn’t ask for much more.
As mentioned, there is a love interest for Giamatti’s Miles – Maya. Here, Virginia Madsen very nearly steals the show from the stellar work from the male pair, however Payne and Taylor really managed to make all four of the leads shine – including Sandra Oh’s Stephanie. Although they don’t get as much screentime as Miles and Jack they need to be there just as much, every one of them needing to learn from the experience they all go through and all of them looking to be better coming out the other end. In lesser hands Madsen and Oh could have easily been wasted and their characters just to serve as plot devices for Church and Giamatti, but much like every other element of Sideways they are balanced with excellent skill.
Throughout all of the events that occur everything still feels very human and very grounded, although beats may be more cinema than real life it never actually feels like that and doesn’t take you out of the story. In part, this is due to the comedic offset against the drama, full of bittersweet moments that we can’t help be laugh at despite the hole that keeps on digging. Mostly with Miles, he seems to keep falling into a pit of his own creation without helping himself from getting out, and though you want to reach into the screen and shake it out of him it still leaves you with a smile on your face.
Nominated for five Oscars in total, it’s no surprise that this is one of the best films of the early 2000’s. With potentially some career bests from Madsen and Haden Church, Giamatti and Oh certainly having their performances in their highlights too, Payne and Taylor make one of their best in an already brilliant list of films and just about everyone else involved bringing their A-game, Sideways is wonderfully complex and human piece that everyone should make the time to see.