← Back to Reviews

I've only seen Sideways twice (I just rewatched it), but it is probably Alexander Payne's best written film. It features two characters, Miles and Jack who both have severe flaws with their lives. They head to wine country for a trip away as Jacks last fling before an impending marriage. Miles is a depressed divorced dude with his last hope in life hinging on his writing skills. Jack is an unhonest man who just loves to have a good time. In a way their journey is a symbol of more danger to their life.

When they get up to Wine Country they meet Mia, who according to Jack wanted to party with them but Miles told her they were just going to crash at the hotel. The encounter between Miles and Jack on their walk back to the hotel is one of my best scene nominations as well. Jack makes it clear that he wants a crazy week to ensue, although that is not exactly what Miles wants. Through their wine touring they also meet Stephanie, whom Jack thinks will be able to fulfill his goals for the week. They all plan to meet for dinner.

You clearly see Miles struggling with his depression at the dinner scene, even so much as to leave the table and call his ex-wife after he has had a few too many drinks. I think Payne shows his characters struggles tremendously and that seen was a great example of that. Everyone as a witness knows that Miles should take a chance at getting to know Mia but he is just stuck on Victoria. And while Jack doesn't think he has a problem, he really does and Payne is able to execute Jacks character as well. Jack finds himself digging a bigger ditch for himself as he continues to fall for Stephanie.

When they all go to Stephanie's house, it forces Miles to open up with Mia and you see his character as a completely different person in a way. He is able to use his love of wine in an effort to open up about his life and to become more comfortable with Mia. He ends up kissing Mia and gives Mia his novel to read, another telling sign that he is ready to move on with his life and open up about things.

As Miles grows up, it seems to me that Jack becomes more and more of a child. Jack goes so far as to abandon Miles from the plans that they had, showing just how little respect Jack is starting to have for the most important people in his life. The transformation of Paul Giamatti's character is one that I think could have deserved an Oscar nomination, while Thomas Haden Church did receive a nomination for his "dirtball character" as well as Virginia Madsen for Mia.

The deception of Jack is tied to Miles as Mia hears about Jack nearing marriage, so much to the point that it affects Miles and Mia's relationship. He then hears that his book has been rejected by the publishers and just when he thought things were taking a turn for the good, he has done another 180. In turn by Mia knowing about Jacks deception, it kills the behind the back relationship that Jack had with Stephanie. Not surprisingly, it comes full circle and Jack and Miles blame each other for their own mishaps. Miles tries to save Jack from his wrongdoings and it affects his life negatively in the end. Just when it seems the friendship might be at a dead end, Miles has to go and get Jacks wallet from the house of his newest fling. Jack realizes everything he has done is wrong and realizes how important Christina is to his life (or so he says). They crash a car so they have an explanation to Jack's nose injury.Can we believe that Jack is sorry for what he has done? This is a question that could go either way. Personally I didn't believe so, but one of Payne's traits is leaving it up to interpretation.

In the end, Jack and Christina get married, and Miles is left to go back to the drawing board. The end scene seems to leave hope for Miles that Mia is a part of that.

The film is filled with so many great lines, but my favorite has to be "I'm not drinking any ****ing Merlot!" Payne has a way of having his actors say the right things at the right time, especially in this film. And the golf scene is one that gives me a great chuckle. I mean who didn't love seeing Jack run after angry men's golf carts?

The funny thing about the film is as a non-wine drinker it actually still makes it appealing to you. The sense of atmosphere that Payne creates in the film gives it a very adventurous touch.

Overall, this is my second favorite movie from Payne but it is not far behind my favorite of his either. I'm glad my REWATCH only strengthened how I feel about the film.