Alexander Payne is part of an exciting wave of filmmakers who grew up during the 1970s and were subsequently influenced by the films from that era. His contemporaries include the likes of Wes Anderson, Paul Thomas Anderson, and David O. Russell to name but a few. And like his fellow filmmakers, Payne eschews the Hollywood trend of placing an emphasis on special effects and trendy actors in favor of character-driven, comedy-drama hybrids populated with character actors like Laura Dern, Matthew Broderick and Kathy Bates.

Payne’s About Schmidt (2002) continued his fascination with American cinema in the ‘70s by featuring one its biggest (and most prolific) stars, Jack Nicholson. His next film, Sideways (2004), continued the road movie motif from Schmidt and combined it with the buddy film. Jack Cole (Thomas Haden Church) is a failed actor about to be married. He decides to go on one last week of uninhibited fun with his best friend, Miles Raymond (Paul Giamatti), a grade school teacher and struggling author. They go on a wine-tasting tour through California’s Central Coast and squeeze in a bit of golfing as well.

Miles is an avid (nay-elitist) wine aficionado while Jack is completely ignorant of wine beyond what tastes good to him and what doesn’t. Miles is trying to get his book published with little success and he’s grown cynical and defeated as a result. Initially, he comes off as an unlikable loser not above stealing money from his mother. Jack counters Miles’ repressed nature by coming off as something of an instinctive kind of person who indulges in his raging id. He was on a hit television show… 11 years ago and is now relegated to doing voiceovers for commercials. Along the way, Jack and Miles meet Maya (Virginia Madsen), a beautiful waitress who Miles knows from way back when, and Stephanie (Sandra Oh), who works at a winery and catches Jack’s eye.

Jack and Miles are complete messes as human beings. They lack direction and are hypocrites. Miles says he’s an author but his book is going nowhere, while Jack is getting married but hits on anything in a dress. They are hardly a sympathetic pair. And yet Payne is able to get a lot of comedic mileage from them. Miles is a wine snob who rambles on about the taste, color, and so on, only to have Jack sum up his opinion simply, “I like it,” which comically deflates Miles’ pontificating. They have an intriguing dynamic. While they lie to others – Miles to Jack’s friends about the status of his novel and Jack being nice to Miles’ mother when he clearly wants to get back on the road – they are no pretenses between each other. These guys are getting to the stage in their lives where they’re looking back as opposed to looking ahead. Jack sees marriage as an institution that will stifle his freedom while Miles has a very negative outlook on life, finding any excuse not to ask Maya out despite obviously liking her because he assumes that it will go nowhere.

An interesting thing happens during the course of the film. At first, Miles starts off as an unsympathetic character while we warm up to Jack’s funny repartee as the charming rogue. Halfway through the film they flip roles and it’s Jack who is exposed as a pathetic womanizer and Miles becomes more sympathetic thanks to Maya’s influence. She humanizes him and is easily his intellectual equal. She knows her wine and this clearly impresses Miles. She’s smart and beautiful so why is she even wasting her time with a sad sack like Miles? She gets to know him beyond his looks and liquefies the pretension of his character. Maya pierces his wine-speak armor that he throws up all the time with her easy-going nature and Miles realizes that he doesn’t need to constantly impress her. There is a nice scene where they get to know each other and it is great to see two skilled actors getting a chance to act and really delve into their characters. In this scene, we finally see someone thaw out Miles and get him to open up, stop worrying and thinking so negatively. They use their mutual love for wine as a way to share their passions and aspirations with each other. It’s a beautifully realized scene because you are seeing two people starting to fall in love with each other. Like a fine wine, Maya allows Miles to breathe and he gets better as time goes on. She’s a romantic who is able to cut through his cynicism and soften his hard edges.

Fresh off the success of American Splendor (2003), Paul Giamatti is one of those actors who make it look effortless as he inhabits the characters he plays so completely. Miles is a neurotic mess; a depressed cynic who is definitely a half glass empty kind of guy. Giamatti is able to tap into his character’s deep reservoir of pain and anger. In a couple of shots early in the film, Payne hints at Miles’ past when he looks at old photographs in his mom’s room. They evoke happier times with his father (now out of the picture) and wife (now divorced). Giamatti’s sad expression in this moment conveys more than any words could. During the course of the film, we find out more about why Miles is so miserable and a lot of it has to do with self-loathing, which explains why he tries to sabotage things with Maya. In some ways, Miles is a variation of Giamatti’s take on the equally acerbic Harvey Pekar in Splendor.

Ever since the short-lived television sitcom Ned and Stacy, Thomas Haden Church has been an untapped resource and with Sideways he was given the role of his career. As Miles’ crass, philandering best friend, he plays Jack as a middle-aged frat boy who still calls women, “chicks.” Haden Church has never been afraid to play abrasive, bordering on unlikeable, characters and he expertly does the same here as a guy who presents a jovial façade but underneath lurks a lot of pain and an insensitive mean streak. Haden Church’s dead-panned delivery of smart-ass lines works well against Giamatti’s uptight straight man. Together, they make an excellent team. After years of playing supporting character roles, it’s great to see Haden Church and Giamatti starring in a film. They play so well off each other that you’d swear they’d acted together before. Haden Church and Giamatti are very believable as long-time friends from the way they interact with each other.

For years, Virginia Madsen has been biding her time in direct-to-video hell and so it is great to see her in a high profile role like this one. From The Hot Spot (1990) to Candyman (1992), she’s always been an interesting actress to watch and with Sideways, Madsen is given strong material to sink her teeth into and she delivers a nuanced performance. Sandra Oh has been quietly building a nice body of work over the years and was unfairly overlooked in the numerous awards that have been lavished on this film. Granted, of the four main cast members, she has the least amount of screen time but she makes every moment she has count.

Producer Michael London was a former Los Angeles Times journalist and studio executive who had become frustrated by the studio development process of shepherding a film from script to screen. He bought the rights to the unpublished semi-autobiographical novel Sideways by Rex Pickett with his own money and gave it to Alexander Payne to read in 1999 while the filmmaker was promoting Election. Payne found himself drawn to “the humanity of the characters” and how it tapped into his desire to make films about “people with flaws,” and “unfulfilled desires.” He was not a wine expert but always liked it and thought that the subculture would be fun to explore and act as a backdrop to the relationship between Jack and Miles. However, he was committed to making About Schmidt next and so he and London kept optioning the book over the years. Then, he and his long-time writing partner, Jim Taylor, wrote the screenplay for free. Payne and London drew up a budget and financed pre-production themselves thereby allowing themselves the kind of creative control they wanted. They only began approaching movie studios once they had the script, budget and a preferred cast in place. Four studios were interested with Fox Searchlight winning out.

Based on the reputation of his previous films, several big name actors campaigned for roles in Payne’s film. Both Brad Pitt and George Clooney were eager to play the role of Jack and met with the filmmaker but it ultimately came down to Thomas Haden Church and Matt Dillon. Edward Norton expressed an interest in playing Miles and Payne seriously considered him for the role. With the exception of Sandra Oh, his wife at the time, all the actors auditioned for Payne and London. Haden Church had auditioned for both Election and About Schmidt (narrowly losing out to Dermot Mulroney on the latter) and even though Payne did not cast him in those films, he had been impressed with the actor. When it came to Sideways, Payne felt that Haden Church “kind of is that character,” and cast him as Jack. At the time, he had moved away from acting and when he read the script in May 2003, thought to himself, “I have no shot at this whatsoever, but I have to answer the call of duty. If I get a chance, then I gotta take it.” When Paul Giamatti auditioned for the film, he had not read the whole script, just an excerpt – the scene where Miles talks about his love of Pinot Noir wine to Maya. The actor found Miles’ obsession with the wine to be “an interesting theme for this guy” who was constantly “striving for transcendence through the wine and the wine milieu, and it just keeps collapsing in on the guy because he’s such a wreck.” After casting Giamatti and Haden Church, Payne insisted that they spend some time together before filming, hanging out and practicing their dialogue so that characters’ friendship would be believable.

The setting of the story was very important to Payne as he brought a documentary sensibility to capturing the people that inhabit the area. Before shooting, he spent four months living in the wine country of California, taking notes so that it would be accurately depicted in his film. The actors spent two weeks of rehearsals with Payne, “shooting the shit and indulging in good food and wine,” according to Giamatti. With a budget in the range of $16-17 million, Sideways was shot over 54 days in the Santa Barbara area. For the look of the film, he drew inspiration from the photographic style of Hal Ashby’s The Landlord (1970), screening it for his director of photography, Phedon Papamichael (Moonlight Mile), in order to study the softness of colors and the lack of sharp, vivid lighting that he wanted in his own film.

Payne’s film harkens to Bob Rafelson’s classic character-driven films from the ‘70s, like Five Easy Pieces (1970) and The King of Marvin Gardens (1972), featuring prickly protagonists. Payne rejects traditional mainstream tastes in favor of presenting unsympathetic characters and a conclusion that refuses to wrap things up neatly. He even employs multiple split-screen montages and snap zooms, which were very much en vogue during the ‘70s. Miles is the voice of reason while Jack is the voice of fun in Sideways. However, Miles understands who he is and is honest with himself and his lot in life unlike Jack who continues to live a lie, or rather play a role. Jack lives in a bubble and they always break. Miles doesn’t have to worry about that because he bursts his bubble on a daily basis. These men are idiots and it is the women who are smart and truthful. The men lie, cheat and are forced to face the repercussions of their actions. This provides them with a chance at redemption as embodied in Miles who learns to loosen up and finally let someone new into his heart.