Alexander Payne is a director and writer whose movies are nothing less than compelling, as seen in his 2023 comedy-drama film The Holdovers. Payne’s films are linked by the writer-director's careful, witty observance of human nature, which is typically embodied through a flawed protagonist whose life is in a state of crisis. Payne’s most fascinating protagonist is Miles Raymond, the tragic hero of his great 2004 comedy-drama film Sideways, in which Miles, played by Paul Giamatti, appears as a divorced, frustrated middle-school English teacher and unsuccessful novelist whose life is defined by failure.

Much like Jack Nicholson’s titular protagonist in Payne’s 2002 comedy-drama film About Schmidt, the middle-aged Miles has asked himself if his life has made any difference in the world and arrives at a grim conclusion. Miles’ unhappiness is manifested through his relationship with wine, which Miles approaches in the guise of a connoisseur, instead of a depression-fueled alcoholic.

Funny, painful, warm, and wise, Sideways is rightfully regarded as being one of the greatest films of the 2000s. However, while the movie is approaching its 20-year anniversary, the film feels ageless. Moreover, like a good bottle of wine, it tastes differently than it did when it was released.

Sideways Is a Bittersweet, Truthful Comedy

As Sideways opens, Miles has reached a level of depression for which each day of his life doesn’t seem to hold even the slightest potential to be a good day. He is unhappily employed as a middle-school teacher, but still clings to a glimmer of hope, which is tied to a novel that he’s written. Miles is waiting to hear from his literary agent regarding whether the novel will be acquired by a small publisher. He also receives a little respite from his misery from the upcoming wedding of his best friend and former college roommate, Jack Cole, an underemployed actor who is seemingly getting married to improve his station in life by entering his future father-in-law’s real estate business.

Jack and Miles embark on a week-long bachelor party trip to California’s wine country, where Jack intends to indulge in a last sexual fling before marriage, while Miles primarily wants to drink. Jack also wants to find a woman for Miles, whom Jack falsely introduces as being a soon-to-be-published novelist, as Miles nervously waits to hear from his agent regarding the status of his novel.

While visiting a winery, Jack forms an attraction to Stephanie, a wine server and single mother who is completely unaware of Jack’s impending wedding, about which Jack expresses increasing doubts. Miles is enamored with Maya, a divorced waitress who is excited about the prospect of Miles being a published novelist but is much more stimulated by Miles’ intricate knowledge of wine, through which Maya and Miles form a psychic bond.

The eventual revelation of Jack and Miles’ deception, for which Jack receives a fractured nose, inspires Miles to seek redemption. After leaving Jack’s wedding, Miles tries to purge his depression and sense of failure by drinking his most prized bottle of wine out of a Styrofoam cup at a fast-food restaurant. Later, Miles returns to the wine country to see Maya, whom the completely vulnerable Miles now has nothing to offer except himself.

Paul Giamatti Deserved an Academy Award For Sideways

Sideways received five Academy Award nominations, including for Best Director and Best Picture, and Alexander Payne received his first Oscar for the film in the Best Adapted Screenplay category. However, while Thomas Haden Church and Virginia Madsen deservedly received Oscar nominations for their performances in Sideways, Paul Giamatti’s brilliant performance was overlooked, in what is surely one of the most glaring oversights in Academy voting history.

Giamatti’s most powerful scene in Sideways is a scene in which Miles and Madsen’s Maya, a woman whom Miles has fallen in love with while on vacation in California’s wine country, discuss the reasons why they love wine. Miles, who is fond of Pinot noir wine, speaks to Maya of his affection for the Pinot grape, which Miles explains is a difficult grape to grow because it ripens early and has a temperamental nature due to its thin skin.

As Miles describes the grape’s vulnerability and talks about the nurturing and patience that’s required to bring the pinot grape to fruition, the audience and Maya realize that Miles is referring to himself. Giamatti deserved an Oscar for this scene alone.

The Holdover Is a Spiritual Sequel

Paul Giamatti received his second Academy Award nomination for The Holdovers, which marks the first collaboration between Giamatti and Alexander Payne since Sideways, to which The Holdovers represents a spiritual sequel. Beyond Giamatti’s appearance in The Holdovers, in which Giamatti plays a cranky professor who is forced to babysit a handful of students at an all-male New England boarding school during Christmas break in 1970, Giamatti’s character in The Holdovers, Paul Hunham, is, like Miles in Sideways, defined by his unfulfilled ambitions, for which Paul, like Miles, is consumed by an unpublished book project.

However, while the nostalgic The Holdovers represents an undeniable triumph for Payne, Sideways remains the most impressive achievement in Payne’s career, in which the core themes of Sideways, in terms of friendship and midlife turmoil, still resonate powerfully. Moreover, Sideways endures as being one of the most impeccably acted, directed, and written films of its era and far beyond.

Nearly 20 years after its release, Sideways, like wine, is constantly evolving and increasing in complexity. However, while wine, as is explained in the film, inevitably declines after reaching its peak, Sideways is alive.