Like a light, summer wine, Sideways might trick you into tasting something that isn't really there at all. Yes, the film features a few passing notes of complexity—a soft examination of depression, a passing glance at regret—but these dissolve neatly by the movie's (not so) surprising final turn. Happily, however, Sideways indulges on character charm and sharp dialogue, each just clever enough to win over viticultural skeptics. You'll feel tricked, though never conned. Wine is more about experience than taste, after all.
Central to this agreeable experience is Miles (Paul Giamatti, delightfully frumpy), who sips and sulks throughout. For its leading man, Sideways quadruples down on generic (white, male, middle-aged, divorced) and miraculously, creates a memorable character. Stuck in a thankless career as a middle school English teacher, Miles lives for his weekend trips to wine country; it's the one activity that can dampen his incessant grumbling to a gentle, fussy purr. So when his college roommate requests a bit of pre-nuptial galavanting, he knows just the trip. In a sneakily impressive balancing act, Giamatti's Miles is pitiful enough to win sympathy but charming enough to remain endearing. Sometimes a few pleasant, believable quirks—a fine vocabulary, an encyclopedic knowledge of wine—can create just as lasting an impression as bipolarity (Silver Linings Playbook), unflinching resolve (Zero Dark Thirty), or state-of-the-art facial make-up (Lincoln).
Meanwhile, Jack (Thomas Haden Church, handsome, reckless) provides a comically exaggerated foil to Miles' tediousness. A forty-year-old Ken Doll, Jack plays the naughty groom-to-be out for one last carnal thrill. The two-man bachelor party soon engage in some classic male one-upmanship, as they (by turns) attempt to be even more boring (Miles) or impetuous (Jack) than before. Wisely, Sideways doesn't saddle Jack with a remorseful epiphany or redemptive change of heart: the film (and from what I've read, the novel it's based on) stays focused on Miles and his many mid-goblet crises.
Leveraging Giamatti's professional whininess, Sideways bets big on spoken word, leaning on bits of banter and snatches of small talk to carry viewers through the first hour of the film. It's certainly a risk—modern movie-goers have little patience for films with slow plots—but the repartee works. Miles' casual lie about "bumper to bumper" traffic (amidst polite laughter) is classic SoCal excuse-making, and his blatant refusal to drink Merlot is priceless. Sideways also tunes its wine descriptions just right: they'll satisfy wine snobs, but they're ridiculous enough that the average moviegoer will spot the satire (Miles: "…a little citrus…maybe some strawberry…passion fruit…and there's even a hint of like asparagus…or like a nutty Edam cheese").
Ask a friend why she loved last Saturday night's wine, and after a few false starts (It had a sweet…no, jammy…well…), she'll probably just smile and say there was something tasty about it. Sideways is much the same way. Don't bother looking for its deeper meaning; don't worry if you just know you liked it. Some films demand thorough cinematic examination. Others simply offer a pleasant taste.
Some Thoughts on Wine
Put simply, I consider the whole wine industry to be a bit of a racket. Please don't mistake me. I enjoy wine regularly. I subscribe to Wine Enthusiast Magazine. I take at least two trips a year to Santa Ynez (Sideways' setting). I'm drinking a glass of wine right now.
But really it's all a profit-snatching scheme, and it's working marvelously well. I know I've been duped, but I continue to buy. I present to you a few visuals:
 By all accounts, wine is the classiest of the spirits. |  And yet, there seems to be no correlation between quality and price. |
 Beer—often ridiculed as a vulgar, classless selection—has an admirably wide range of tastiness. Selecting the right beer is incredibly important. |  But wine? Most wine tastes pretty good, but not great. While there are certainly some stinkers, there really aren't many true standouts. |
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