Rated R for language, some strong sexual content and nudity.
126 Minutes
Written and Directed By: Alexander Payne
Based On The Novel By: Rex Pickett
Staring: Paul Giamatti, Thomas Hayden Church, Virginia Madsen, and Sandra Oh
No, if anyone orders Merlot, I’m leaving. I am NOT drinking any fucking Merlot! -Miles
Review
Two middle aged guys have reached the halfway mark of their life expectancy, and have done very little to inspire the next half of their lives. Goals, hopes, and dreams, still exist in some fragmented place in their hearts, but their desires and ambition to aspire or attain those goals has long since simmered. A week in wine country getting drunk, being morally ambiguous, while sulking about their failures and reflecting on the pathetic existence that is their lives is the content which fills this two hour long film. Is this funny? Go ahead and start throwing your Chinese flying stars at me, but I did not find Sideways to be funny at all. It was actually a shocker after which upon description and reviews I’d read prior would have lead me to believe this dark comedic character study would have been right up my ally, but……….not so much.
I’d like to blame it on the rain here, but being a fan of the jaded soul, the dark comedy, and the twisted sense of humor that is closer to reality than is comfortable for most people, I lament at saying Sideways never made that connection or reached that level of greatness. It never maintained a quality that made me at least enjoy the self loathing or destruction of our characters, instead I felt more or encouraged to join the pity train, and instead of laughing and begging them not to make the same stupid choices over and over again, it’s just felt arid of any hope or humor.
The only true light of sideways was Virginia Madsen. She incorporated the ideal of the failed dreams but still existing, and 
maintaining her humanity. Smart and resolved in who she was, halfway through I began to wonder why she was attracted to Miles at all, except it seemed she clearly wanted to punish herself. The only redeemable and enjoyable part of the story was the discussion between herself and Miles and discussing when they’d fallen in love with wine, and why it was so special to each of them. The adoration was genuine and the connection they made was palpable.
Usually in this brand of film you find yourself laughing at the characters stupidity or behavior, but here they were so unforgivable and so unlikeable it just wasn’t possible. Beyond that, it got repetitive and boring. At times I felt like Miles friend yelling at him to get over his drinking, his wife, and his depression about his book. But I also felt like Miles yelling at his friend for being such a selfish, unscrupulous jerk. These characters need redeemable qualities to compensate for the fact that they are unlikable morally compromised imbeciles, but I never got that.
I know I’m probably one of the few, but Sideways just didn’t win me over. What? Was that another Chinese flying star? Enough already! I mean, I love Paul Giamatti , he’s a great actor, but his morose depressed nature was far too overwhelming to get the necessary laughs I needed from this movie. At certain points I was just hoping it would end, and I could be over it. I even waited a few days to let it sink in and see if it would have the Swingers affect, where upon reflecting I seemed to catch on to the sense of humor, but that never happened. The humor here was clear, it just failed miserably. There is no resolve or pondering epiphany at the end, it was just two hours of watching two other people waste their lives away while you are doing the same by watching it.
I’d always wanted to see this but I fear that I may feel the same way that you do about this one. Of course I’m a glutton for punishment so I may still watch it, it just won’t be my first choice, maybe more like my 150th choice!
Yeah, I know other people out there had to of found this as pretentious and self indulgent as I did. I’m hoping they’ll hop on my bandwagon and tell me so!