August 8, 2016
Sideways (2004)
Grade: 60/100

Director: Alexander Payne
Stars: Paul Giamatti, Thomas Haden Church, Virginia Madsen

What it's about. Set in California. Two forty-ish best friends, Miles (Paul Giamatti) and Jack (Thomas Haden Church), go on a road trip together for the week prior to Jack's wedding to Christine (Alysia Reiner), an attractive woman whose family has money.

Miles wants to spend the week wine-tasting and playing golf, but Jack has other ideas. He wants to get laid. He finds his target in gregarious Stephanie (Sandra Oh). She is friends with waitress Maya (Virginia Madsen), a classy waitress acquaintance of Miles, and soon Jack finagles double dates, even though Miles is recently divorced and still mooning over his lost wife.

It all ends badly, due to Jack's lust and wishful thinking, and Miles' honesty, hardly an asset given the company he keeps. Yet the movie ends better than one could have expected.

How others will see it. Director Alexander Payne has for many years enjoyed a favorable reputation as a filmmaker. Sideways was also a box office hit, and has a big 150K user votes at Thus, it is hardly a surprise that the movie won the Oscar for Best Screenplay, which Payne shared with Jim Taylor, who also helped write two of Payne's successful previous movies, Election and About Schmidt.

The film also won Best Screenplay at the Golden Globes, as well as Best Comedy. It was nominated for five other Golden Globes, and four other Oscars, all in major categories.

The user ratings are high but a gender gap is significant (7.6 among men, 7.1 among women). Women may disapprove of Jack's lies and women-chasing, and they may disapprove of Miles simply by choosing to be friends with Jack.

How I felt about it. If this is a comedy, why is it so depressing? True, these are fictional characters, so if Jack drives Miles' car into a tree, or even a ditch, no animals (even humans) were hurt in the making of this film.

Still, it is a downer when a tipsy Miles leaves his promising date in the middle of dinner to make a long distance phone call to his remarried ex-wife. It is upsetting (and far from hilarious) when Stephanie pummels the face of hapless Jack with her motorcycle helmet.

So, this is a black comedy, in the spirit of those cheap slasher movies in which good looking teenagers are slaughtered for our cynical amusement. All except for the cutest girl, whose fast feet and primal screams keep her one step ahead of her grotesque and blade-swinging assailant.

In that sense, Sideways is like at least two prior films directed by Alexander Payne that purport to be comedies, Citizen Ruth and Election. Both are even better than the present movie, perhaps because Sideways wimps out. Jack gets the happy ending (marriage to the heiress) that he doesn't deserve, and it looks like Miles will get Maya despite being the best friend and/or accomplice of a pathetic womanizer.

It is true that audiences probably want Miles to end up with Maya, although she can do better than a balding, overweight, alcoholic, depressed middle-aged grade-school teacher and unpublished author. Jack is more deserving of Cammi, that is, somebody as impulsive and irresponsible as he is. California is a community property state, and Christine is likely to be confronted with the prospect of enriching the man who cheats on her in order to be free of him.

Sideways also reminds me of those odd couple road movies, especially Il Sorpasso (1962), where the fun-loving jerk who gets in trouble is paired up with the joyless schmuck, to the detriment of the latter. Both even have a car accident. It is true, though, that Miles would never have had a romance with Maya if it were not for Jack's indifference to Miles' inhibitions.

I am still uncomfortable with Stephanie beating Miles with her helmet, breaking his nose, because he lied to her. It is not a crime to withhold an upcoming marriage from a love interest. It is a felony (assault with a deadly weapon) to beat somebody with a helmet.