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Directed by

Alexander Payne

 Sideways Poster

Review by Todd Plucknett


Sideways is an absolute masterpiece by writer-director Alexander Payne. It is flawless on so many levels, particularly the screenplay Payne wrote with Jim Taylor based on Rex Pickett’s brilliant novel of the same name. It is the most intelligent and mature screenplay of 2004 and one of my favorites of all time.

The film kicks off with one of the best opening lines ever, in which obviously hung-over 8th grade English teacher Miles Raymond (Paul Giamatti) unleashes an expletive as someone is waking him up with the sound of knocking on the door. He realizes that he is running extremely late and that he needs to be picking up his friend in about an hour for a trip that he has not yet packed for. He gets his things together and gets on the road.

He shows up to pick up his actor friend Jack (Thomas Haden Church) from his fiancée��s parents’ home very late, and then the two of them take off on the road trip for the Santa Ynez wine country. Jack is set to be married the following Saturday to Christine (Alysia Reiner), and this trip was slated to be a last week of freedom the two best friends. The plan is to play golf, eat great food, drink great wine, and send Jack off in style. However, Jack��s main goal is to take advantage of his one last week of sexual freedom before getting married and bring Miles, the divorced, chronically depressed and unpublished author, out of his despair by getting him laid.

The two men meet Maya (Virginia Madsen), a waitress that Miles had encountered before on his several visits to that area. At a winery, they meet Stephanie (Sandra Oh), a single mother who knows Maya and immediately hits it off with Jack. Jack arranges for the four of them to go out that night. They told neither of the two ladies of Jack’s upcoming wedding. Jack claims to have fallen in love with Stephanie after one day, and is thinking about putting the wedding on hold to make sure that he is making the right decision. Miles, who obviously has strong feelings toward Maya, is struggling with the whole situation because he still has feelings for his recently remarried ex-wife Victoria (Jessica Hecht). These relationships form the core of the film, and you really begin to love every one of them.

This is one of the best acted films of the past several years. The ensemble cast has chemistry unmatched by almost any film this decade. Giamatti received one of the most appalling Oscar snubs of all time. His role encompassed so many emotions and required so much from the actor, and his performance came off as thoroughly believable and absolutely flawless. Church was a revelation as Jack. His role was complex, and he pulled it off, creating perhaps the finest character of the year. Madsen was mesmerizing in every frame. Nobody could have done a better job than her. Oh was very good as well. She fit in well with the other characters nicely but being overshadowed slightly by the astonishing lead performances.

Sideways is about the most articulate screenplay I have ever come across. The vocabulary, mass knowledge of media, and knowledge of everything wine is what puts it on another level. This was really my education on wine (and probably for many other people, considering the significant increase in Pinot sales and decrease in Merlot sales following the release of this film…you’ll know why after seeing it). Many would say that the movie is about wine, but it is about so much more. It not only used wine as a bridge to bring characters together, but it also is a metaphor. There is one phenomenal scene in particular in which Miles and Maya are sitting on the back porch at Stephanie’s house. Miles goes on talking about his favorite win, Pinot. About midway through talking about why he likes it, Maya realizes that he is not just talking about wine but that he is also talking about himself. This is the shining scene for Madsen. She then goes on talking about why she got into wine, letting Miles know that there is so much more in life than what he lets tear him down. That scene is perfectly acted and brilliantly directed. The film also has some hilarious scenes to go with the subtly funny scenes and the brilliant drama. The scene on the golf course is an example of how the film can be simply uproarious.

Above all, the film is about the characters. It has four characters that are totally lovable and flawlessly developed. It is guaranteed that you will see something of yourself in Miles. He has so many problems in his life, and these are human problems. His personality is the polar opposite of Jack’s. It is amazing that these two can be friends, but they are. They love each other, but they don’t necessarily understand one another. Jack seems to be a jerk and seemingly have no conscience, but then you see his vulnerability, and you realize that he is just another guy with his own problems. Giamatti and Church became these characters; it seemed so natural that it was as if they were not acting. Since watching it, I cannot see Giamatti or Church without seeing Miles and Jack. These are two iconic and career-crowning performances.

Sideways is just about the most intelligent, witty, and rewarding comedy-drama there is. Its insight into relationships and motivations of why people do what they do is outstanding. There are countless priceless shots in this film. It is endlessly quotable and fully appealing. The score is just lovely, totally suiting the mood for every frame of the film. Every scene has an idea, and not one seems unnecessary. It is both touching and ultimately satisfying. Anyway, I could write about this movie all day. It only gets better with multiple viewings. There are more things that you will catch each time seeing it, and your appreciation for the film will only grow with age. For me, it is necessary to watch it about monthly to satisfy my thirst for the film. It is basically the cinematic epitome of a perfectly written, acted, and affecting comedic drama.


# 3 on Top 100

# 1 of 2004

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