Sideways tells the deceptively simple tale of two middle-aged friends who drive up the Californian coast together to spend a week tasting wine. The trip is to celebrate the impending wedding of Jack (Thomas Haden Church), a down-on-his-luck actor who's landed himself a wealthy fiancée. Accompanying him is Miles (Paul Giamatti), a schoolteacher and aspiring novelist who has been his best friend since they shared a room in college. The two men are polar opposites: Miles is cerebral, introverted and a bit of a miseryguts while Jack is shallow, outgoing and able to look on the positive side of everything. For example, when asked about his career, he tells people he does commercials. The truth of what he actually does in them provides one of the biggest laughs in the film.
The wine-tasting holiday is Miles's idea. Wine is his hobby. He can swirl a glass around, sniff it, take a taste and tell you everything about it bar the phone number of the guy who picked the grape. Jack on the other hand will knock back whatever he's handed, say it tastes fine to him and keep his eyes on the waitresses. Jack views the vacation as a last chance to indulge his passion for chasing women before making his marriage vows. He's also determined to get Miles laid. His pal has been alone and in a funk since his divorce two years ago.
Opportunities present themselves in the form of Maya (Virginia Madsen) and Stephanie (Sandra Oh). Maya is a pretty waitress Miles knows from previous trips. Stephanie is a lonely single mother who shares Jack's appetite for sex. It's not long before the bridegroom-to-be is sharing her bed and filling her ears with promises he can't keep. Miles and Maya like each other but both of them have had their confidence and faith in the opposite sex damaged by divorces. Miles is particularly reluctant to make a move and has to be virtually press-ganged into a double date by his exasperated friend.
Sideways is a great comedy and a lot more besides. It's not above cheap jokes and slapstick when there are big laughs to be had from them but most of the time it's funny in a very truthful way. The comedy comes out of watching people say and do the kinds of outrageous things that real people actually say and do. This is the kind of film that makes you wince with recognition while you're laughing. It opens some of the same wounds that Closer does.
Director Alexander Payne and his writing collaborator Jim Taylor have built their reputations on mixing humour and stinging observation. Their last two projects, Election and About Schmidt are two of the most memorable comedies of recent years. Sideways is the best film they've made, the funniest and also the warmest. Payne and Taylor are still exposing everyday human weakness with their satire but the cynicism of Election has given way to a more generous and hopeful outlook. For all their faults, Miles and Jack are two of the most sympathetic movie characters you're ever likely to see.
Miles will be painfully familiar to anyone who's ever felt like a failure or grown bitter about their lot in life. You cringe on his behalf but it's impossible not to empathise because we've all been there at one time or another. Jack is also absolutely 100% accurate. I have a friend the character could be based on and another one not far off. Larger than life guys like Jack behave the way they do simply because they can get away with it. They're easily forgiven since they're the kind of guys everyone enjoys being around. They're the life and soul of the party, they make you feel bigger when you're with them and they provide an endless stream of anecdotes to make other people laugh. The details of these two men, the bond between them, their relationships with Maya and Stephanie: everything feels right.
There's been some debate on the Internet Movie Database about the moral failings of the two leads, neither of whom would get out of a Catholic confession box without a stern telling off and a few hundred Hail Marys. These moralists are missing the point but it's a testament to how well this film works that people are judging its characters like real people. It's films like Sideways and Million Dollar Baby that inspire these arguments. No one's getting indignant about the dubious ethics of Jude Law's Alfie.
Sideways couldn't reach the heights it does without a great cast and it has one. Paul Giamatti has played nerds and losers before, most memorably in American Splendor but also in movies like Storytelling and Duets. He's such a distinctive actor, both physically and vocally that it's all the more impressive that he makes each of these characters distinctive and completely original. Miles is his best and most subtle creation to date. It's disappointing that the Oscar nominations passed him over.
At least there were nods for Thomas Haden Church and for Virginia Madsen, who is expected to win Best Supporting Actress. Madsen's a familiar face from films such as Candyman and The Hot Spot but she's never been given a part like this or dialogue like she has in her scene on the porch with Miles. Church has appeared out of nowhere - I thought I recognised him and it turned out he's the guy Val Kilmer winks at in the OK Corral scene in Tombstone. The way he breathes life into the comic stereotype of the woman-chasing, out-of-work actor - Joey from Friends! - should rightly win him a statuette too. Completing the quartet is Sandra Oh, who was memorable as Diane Lane's pal in Under The Tuscan Sun and doesn't let the side down here either.
Of the five films nominated for Best Picture this year at the Oscars, I've disliked one (Finding Neverland), liked another (Ray) and loved two (Million Dollar Baby and The Aviator). Sideways is the best of them and probably the best of all the films I've seen which are eligible for a nomination. It's unlikely to win - Oscar doesn't appreciate comedies, even ones as smart as this - but it's enough consolation that the publicity is getting this great film seen by a wide audience. There are a number of fine movies in cinemas now that are worth your attention. Make sure Sideways is at the top of your list.