Sideways (2004) is an excellent film about the topsy-turvy nature of middle-age life and how to cope with the curveballs that life throws at us to challenge us. Critically acclaimed at the time and nominated for many awards, Sideways, directed by Alexander Payne is a good tale about male friendship, how to deal with mid-life problems, and finding love and purpose during difficult times.
The very title of the film ‘Sideways’ is symbolic of the best way in which wine bottles should be preserved by being laid on its’ side in order to age properly. Also, men and women who are going through their mid-life ‘sideways’ must embrace the challenges that lie ahead and the changes that come to them with this part of life in order to grow and mature as a person.
The basic premise of the film ‘Sideways’ involves two middle-aged men who are close friends, Miles Raymond (played by Paul Giamatti) and Jack Cole (starring Thomas Haden Church) that decide to take a week long Bachelor’s trip up to the wine country of Napa Valley in California to celebrate Jack’s upcoming wedding and the end of his singledom. Both of these men are in their forties and have a sinking feeling that the best of life is behind them.
Miles is in a depressive state due to the fact that he feels like a failed writer due to the uncertain future success of his yet-to-be published book. While he has a steady job as a high school English teacher, he feels unfulfilled by his life and wants to achieve greater success as a novelist but has yet to break through. On top of that, he has gone through a recent divorce that he has yet to recover from fully and is newly single.
Luckily or unluckily for Miles, he has a friend, Jack, who is hoping to have a good time for his last few days as a single man. Jack Cole, Miles’ friend is an actor who may be past his prime. While he used to be a TV soap opera star years ago, now, he is mostly relegated to doing voiceovers for silly commercials and seems to be getting tired of the acting business. Jack loves his fiancé but has the problem of not being able to control him when it comes to women.
Unlike Miles, Jack is not a big wine connoisseur and is more into playing golf and hooking up with a local woman before he takes those fateful steps down the aisle. Jack is hoping to not screw up his marriage but he obviously misses the single life while his friend, Miles dreads being single again. Jack may love his fiancée but he is also hoping to get involved with the real estate business that his soon-to-be father-in-law is running in Los Angeles, which Jack wants to be apart of in order to get away from acting once and for all.
Beyond just writing novels and teaching his students, Miles’s true passion in life is wine, which is why he proposes Jack that they go to Napa Valley to drink some great wine, play some golf, and eat some good food together. While Jack enjoys all of those activities, he has other plans in mind for his last days as a single guy leading to hilarious and disturbing results for the both of them. Before Jack wants to get married, he wants one last fling as a ‘single’ guy before he becomes the husband to his wife. In the meantime, Miles encounters a woman he never expected to meet.
Maya, (played by Virginia Madsen), is a kind and intelligent waitress at a local restaurant in Napa Valley known as ‘The Hitching Post II.’ She is someone who Miles has encountered before during his previous solo trips to Napa Valley. While they were friendly to each other, it’s only on this Bachelor’s trip to the wine country where Miles with the help of Jack’s support gets to know Maya better. Maya and Miles really hit it off with each other especially over their shared love of good wine and they start to develop a relationship.
Luckily for Jack, Maya knows a local wine keeper, Stephanie, (played by Sharon Oh), who has a lot of the characteristics that Jack likes in a woman. The two men end up dating and hooking up with both women but with unforeseen and negative consequences. Jack’s adulterous philandering almost catches up with him and causes Miles a lot of unneeded stress. Miles also suffers during this trip from the lack of hope for his novel in finding a publisher to sell and advertise it.
He also struggles to give up on his ex-wife, Vicki, who he did cheat on leading to their divorce and breakup. The almost breaking point for Miles comes when he finds out that his ex-wife, Vicki, got re-married and has a newborn daughter causing him to regret his divorce from her. While his wife has moved on from him, he still struggles with the fact that his book is going nowhere, he is single in his 40’s, and has no legacy or children at the moment.
Despite all of mid-life struggles that both Miles and Jack go through during the film, they remain loyal and true friends despite the pain and suffering they cause each other. Miles and Jack are almost complete opposites of each other in terms of their personality and character. Miles is serious yet forlorn and an intelligent, well-spoken man while Jack is a cocky womanizer who never really grew out of his teenage years.
However, despite their differences from each other, they do help lift each other out from their problems. Jack gives Miles encouragement to keep working on his novel and to self-publish it if he has to. He wants Miles to succeed at starting a relationship with Maya and really gets him to start going out with her. Miles saves Jack from himself multiple times throughout the film and even though Jack’s integrity is compromised, Miles is there to clean up the damage and makes sure that his friend follows through on his marriage commitment to his fiancée, Stephanie.
Every character in this film is flawed in some way and even though each of them, both men and women, are in their forties, they still have some growing up to do and don’t have everything figured out when it comes to life. Each of these characters has their own personal demons with Miles having depression and a lack of success in his passion and Jack being an adulterer and a compulsive liar.
While they are not perfect men and the women they are involved with make that clear to them, they are still good guys at heart and want to do the right thing. Life has thrown them ‘Sideways’ and they are trying to keep up with all of the curveballs that they must dodge and move forward against. It is really no surprise to me that similar to ‘Lost In Translation’, this film has become a cult classic that can warrant multiple viewings.
While it may not be your typical feel good movie, it’s a ‘real’ film about ‘real’ people who are trying to succeed both personally and professionally against the odds. If you decide to watch ‘Sideways’ for the first time, you’re going to be rooting for each of these characters to find happiness. They are endearing to us as the audience because they make mistakes and have setbacks just like those of us watching the film. In addition to the brilliant acting especially by Virginia Madsen, Paul Giamatti, and Thomas Haden Church, the adapted screenplay is brilliantly written and thought out.
Even though most viewers would consider it a dark, morose film, it also has a lot of comedy in it and some great lines about wine. There are a lot of moments in ‘Sideways’ that will make you sad, happy, angry, and even make you relate to the characters themselves. A great film overall directed by Alexander Payne, Sideways was released way back in 2004 but still remains a popular and heart-warming film that will leave you satisfied. I highly recommend checking ‘Sideways’ out when you get the chance and to remember after watching the whole film to never order a tall glass of Merlot again.