Alexander Payne’s About Schmidt, featured a retiree looking back over his life with a sense of underachievement. His new film, Sideways, returns to the themes explored in his breakthrough film, Election, with two men nervously approaching middle-age. One is on the cusp of an unwelcome marriage while the other awaits a final shot at becoming a published novelist. For each, the passing days mark a narrowing of opportunities and a last ditch attempt at finding some solace, from either a woman or a bottle of wine.

The film follows the week-long journey undertaken by Miles and Jack, buddies-of-sorts since they shared a dorm at college. Jack, with his classic all-American looks, has spent much of his post-collegiate life as a d-list actor whose voice has been used in countless radio ads and is remembered by some as a central character in a long-since defunct daytime soap. Aware that his dream of success is unlikely to happen, he asks for his girlfriend’s hand in marriage and accepts a position in her wealthy father’s company. To see out his last week of bachelordom, he agrees to accompany Miles on one of his wine-tasting trips. The antithesis of Jack’s tanned persona, Miles is everything California – or the image of it – is not. Introverted, moody, depressive, cynical and bitter over the break-up of his marriage, which ended two years earlier – the result of his infidelity – Miles sees the trip as a chance to bond with his old buddy, unaware that sex – with anyone – is all Jack has on his mind.

Payne and co-writer Jim Taylor’s adaptation of Rex Picket’s as-yet unpublished novel is a reminder of the independent spirit that fuelled the classic movies of the early 70s. And like the best work of Bob Rafaelson and Hal Ashby, the film’s freewheeling narrative belies the control with which the director assembles each scene. The beauty of northern California’s vineyards is contrasted with the abrasiveness of the friends’ banter and Jack’s increasingly erratic behaviour, steering the film clear of sentimentality and offering a more complex study of two troubled men.

Like both Andersons (Wes and P.T.), Payne displays a unique ability to draw out fine performances from his cast. Paul Giamatti once again plays dispossession to perfection as Miles. Although it will likely remain overshadowed by his portrayal of Harvey Pekar in American Splendour, Giamatti captures the pain and anguish of a man attempting to find a reason for life. Equally impressive are Virginia Madsen and Sandra Oh. Also troubled by failed relationships, they are more centred because of their work and the passion they have for the wines they grow, serve and drink. Attuned to other peoples’ feelings, they balance the film, countering Mile’s intellectualising and Jack’s bravado with wisdom and maturity.

It is to Thomas Haden Church’s credit that in such a finely crafted film, his portrayal of Jack should stand out so much. An actor whose CV is not so different from the character he plays (his previous role was the lead in Serial Killing 4 Dummys ), Church delivers on all fronts, playing Jack’s foul mouthed and feeble minded egoist with such gusto even Giamatti’s nuanced performance is frequently nudged aside. Previously memorable for a reptilian cameo as an ad exec in Mike Figgis’ One Night Stand, Church’s performance, at once cartoon-like yet utterly credible, is one of the few genuinely deserving contenders in the approaching awards season.

Avoiding condescension and trite characterisation, Sideways manages to be both poignant and very, very funny. Payne and Taylor’s writing displays an emotional depth their previous work only hinted at and, in its closing moments, with Miles wearing a rare expression of hope, the film offers a bittersweet cliff-hanger that, like Richard Linlater’s Before Sunset, leaves you moved by its wistfulness and humanity.