Directed by: Alexander Payne
Written by:Alexander Payne, Jim Taylor
Starring: Paul Giamatti, Thomas Haden Church, Virginia Madsen, Sandra Oh
Released: January 26, 2005
Grade: A

How can I aptly describe Miles Raymond?  Miles (Giamatti) is a man who can find the negative in any positive.  His wife left him two years ago and he hasn’t been remotely intimate with a woman since.   He has drafted several novels but all have been written-off and passed over by publishers.  He lives alone and works monotonously as an 8th-grade English teacher.  All this has left Miles “officially depressed”.  His life is a joyless existence and he’s out there looking for the next kick in the teeth.

Best friend Jack (Church) is to be married in exactly one week.  To send him off, Miles has planned a week long trip across the wine regions of California.  Miles sees it as a chance to bond with one of his few good friends by playing some great golf, eating some great food, and drinking some great wine.  Jack sees things differently.  For him, the week is about sex.  He wants to get laid as many times as possible before Saturday’s wedding.

The differences come to a head when Jacks meets two girls, Maya (Madsen) and Stephanie (Oh), and invites them to dinner.  Over a few expensive bottles of red wine, Jack and Stephanie hit it off immediately.  Miles however, stumbles through the whole evening.  Maya shows a keen interest but Jack retreats into his shell.  Instead of seizing the opportunity, he focuses on the doomed relationship with his ex-wife – to the point where he calls her from the restaurant’s public phone and pleads for her to take him back.

When the four head back to Stephanie’s house, Jack and Stephanie head to the bedroom while Miles and Maya uncomfortably sit on the porch.  Looking to avoid talk of anything remotely intimate, Miles turns to his favourite topic – wine.  Their conversation is one of the film’s highlights and one of the best written pieces of dialogue I can recall.  That’s all I’ll say at this point.

The rest of the film I will leave for you to discover.  You will go a long way to find a quartet of better performance.  They are all troubled people but each in their own way.  The consensus amongst critics is that the reason the film has been so well received is that there’s always at least one of the characters with whom the viewer can identify.

I have been a huge fan of director Alexander Payne since he made the under-rated Election with Reese Witherspoon in 1999.  On the surface it’s a comedy but there’s a much darker layer just below.  Whilst it is not quite as good, Sideways is of similar design in that it doesn’t fit into one genre.  There are moments of hilarity, moments of tragedy and moments of romance.  I have been so critical of romantic comedies over the past few years but here’s a film which successfully takes a different approach.  The relationship between Miles and Maya is gut-wrenchingly real.  They may not have the looks of a Ben Affleck or a Jennifer Lopez but you’ll find Paul Giamatti and Virginia Madsen leave much more of an impression.

Although the Oscar nominations have not yet been released, Sideways is a shoe-in to receive many of them.  The two most powerful critic groups in America, those of Los Angeles and New York, each voted Sideways as the best film of 2004.  Not since Saving Private Ryan in 1998 have both groups crowed the same film with its best picture honour.  I don’t see it as the year’s best film but if putting together a top 10 list, I wouldn’t want to overlook it.