Sideways is directed by Alexander Payne and it tells the story of two old friends embarking on a week long journey to Santa Barbara County in California. Miles (Paul Giamatti) is a divorced English teacher who is struggling to get his book published and he is a borderline alcoholic and socially awkward. He takes his soon to be married friend Jack (Thomas Haden Church) on this trip; Miles is an oenophile and his idea of a good time is attending wine tasting events. Jack on the other hand is a bit of a womanizer and he sees this trip as his last chance to get laid before getting hitched with his beautiful Armenian-American bride to be. He was once a fairly recognizable actor on a soap opera, but now he tells people he does voice overs in TV commercials but he is actually the guy that rambles about warnings for side effects at the end of medical advertisements. Miles and Jack are polar opposites who were roommates in college and you wonder how they remained friends after all these years.
The wine tasting scenes are comedy gold as Miles who knows all there is to know about wine examines and admires the texture and odor of every wine while Jack is just clueless and doesn’t share Miles’ love for wine. In one of the funniest scenes in the film, Miles is showing Jack how to smell wine and detect all its flavors, and after spending all that time preparing for the tasting Miles discovers that Jack was chewing gum the entire time which makes the tasting futile. After their first tasting, they stop by Miles’ favorite restaurant (The Hitching Post) where we meet Maya, a waitress that Miles is acquainted with and has great admiration for. Jack being Jack asks Miles why he hasn’t made a move on her and tries to be his wing man to get him laid but that proves to be difficult since Miles won’t work with him. The next day they meet Stephanie who is a pour girl at a winery tasting room, and after Jack makes the connection that Maya and Stephanie are friends he sets up a double date. He urges Miles not to mention anything about his upcoming wedding and also tells him to get loose and not be depressed. Miles has not gotten over his divorce and the whole trip sort of reminds him of his ex wife since they used to go wine tasting and you feel the sense that he is thinking of her every time he drinks wine so it is difficult for him to be involved with anyone.
Their first night together doesn’t go according to plan, while Stephanie and Jack are hitting it off Miles on the other hand is getting very drunk and is ranting on and on about wine; Jack constantly looks over his side of the table with disappointment. When the ladies go to the bathroom Jack tells Miles how much of a bore he was and asks him not to ruin this; he also asks him if he drank and dialed which he did. The phone conversation is so awkward as his ex wife has a new life with a new husband, but at the same time it is also heartbreaking since Miles is still very much in love with her; this drunk dialing thing must have happened before since Jack picked up on it and even his ex wife asks if he was drunk on the phone. The interactions between these characters is something to behold as it’s very natural; it is at times cringe worthy. Jack is determined to get laid as he is making Stephanie feel like the only girl in the world, but he goes way past that and starts hanging out with her family and starts to question his marriage out of the blue and he thinks he is in love with her. Miles on the other hand is slowly falling for Maya; in one powerful scene, where Maya has a monologue about the life of wine and how precious and alive wine is, you can actually see Miles seeing her in a new light and falling hopelessly for her. Miles feels he is doing no wrong by concealing the fact that Jack is engaged and still hopes to start a relationship with Maya. As an audience, you’re just waiting to see how long Jack can keep up his false pretenses and how Miles is going to overcome his fear of life.
The acting in this film is superb and the conversations the characters have seem unscripted and believable. Paul Giamatti plays Miles so naturally and too convincingly that he is depressing to watch in the best possible way. Thomas Haden Church is hilarious as Jack and he is so naive and lovable but at the same time despicable. The ladies of Sideways, Sandra Oh and Virginia Madsen, are both great and add so much to the film’s charm. I learned more about wine in this film than I did in my wine processing class in college; this movie will have you craving wine, especially Pinot Noir but definitely not Merlot, never Merlot! Sideways is one of my favorite movies of all time and every time I revisit the film I am floored by how beautiful this movie is and it is nothing short of perfection. (10/10)