Ever since Alexander Payne's 'Sideways' uncorked a cultural phenomenon in 2004, it's become a critical shorthand. But what does it really mean when a review calls a new movie 'Sideways-esque'? It's more than just wine and road trips.
The 'Sideways' Blueprint
Before we dive into
the films, let's define the formula. A 'Sideways' comparison usually signals a story centered on a specific type of character: the middle-aged man marinating in melancholy. He’s often a failed or struggling creative (a writer, a teacher) who feels life has passed him by. This protagonist is typically paired with a more hedonistic, charismatic buddy, and their relationship fuels a journey—literal or metaphorical—marked by darkly funny, often cringe-inducing misadventures. The setting is usually a niche subculture, like the Santa Ynez wine scene, which the main character treats with pretentious reverence. At its heart, it’s a bittersweet comedy about failure, loneliness, and the faint hope of a second chance.
1. The Holdovers (2023)
This is the most direct spiritual successor, reuniting 'Sideways' director Alexander Payne with star Paul Giamatti. The comparison is almost too easy. Giamatti once again plays a curmudgeonly, intellectual teacher, this time at a 1970s boarding school. Instead of a wine trip with a friend, he’s stuck 'holding over' Christmas break with a troubled student and the school's head cook. The core elements are all there: an unlikeable but sympathetic protagonist, an unlikely bond that forces self-reflection, and a contained, atmospheric setting. Critics noted that 'The Holdovers' is Payne's most 'Sideways'-like film since the original, calling it his best work in years and praising its blend of sharp humor and aching sadness.
2. Nebraska (2013)
Another Alexander Payne film, 'Nebraska' fits the mold but swaps the lush California vineyards for the stark, black-and-white landscapes of the Midwest. The buddy trip here is between an aging, dementia-addled father (Bruce Dern) and his weary son (Will Forte). The father is convinced he's won a million-dollar sweepstakes and is determined to travel to Nebraska to claim it. The film shares that signature Payne blend of deadpan comedy and profound melancholy, exploring themes of family disappointment, aging, and the quiet desperation of small-town life. While the central relationship is father-son rather than two friends, the dynamic of one man's delusion forcing another's reluctant journey of discovery is pure 'Sideways'.
3. About Schmidt (2002)
Released two years before 'Sideways,' this film is arguably where Payne perfected the template. Jack Nicholson plays Warren Schmidt, a recently retired and widowed man who embarks on a soul searching road trip in his Winnebago to stop his daughter's wedding. 'About Schmidt' established Payne's fascination with the quiet despair of the American male adrift in late middle age. Schmidt, like Miles in 'Sideways,' is a man grappling with a life of perceived mediocrity and regret. Critics retroactively point to 'About Schmidt' and 'Sideways' as companion pieces, two sides of the same coin exploring loneliness and the clumsy search for meaning after life fails to go according to plan.
4. Another Round (2020)
This Danish film, directed by Thomas Vinterberg, proves the 'Sideways' formula transcends American cinema. It follows four high school teachers who, mired in midlife crises, decide to test a theory that maintaining a constant low level of blood alcohol will improve their lives. Alcohol here serves the same function as wine in 'Sideways': it is both a liberator and a catalyst for chaos. The film captures the male bonding, the initial thrill of breaking from monotony, and the inevitable tragic consequences. While it has a different cultural flavor, its exploration of middleaged male malaise and the use of a substancebased 'experiment' to rediscover a zest for life made it a frequent point of comparison for critics.
5. The Land of Steady Habits (2018)
Nicole Holofcener's film centers on Anders Hill (Ben Mendelsohn), a man who has proactively blown up his life by retiring early and divorcing his wife, only to find himself adrift in a wealthy Connecticut suburb. He feels trapped by the 'steady habits' of his uppermiddleclass life and engages in a series of poor decisions, including doing drugs with a troubled teenager. The film is a biting portrait of suburban ennui, hitting familiar notes of male regret, poor impulse control, and the awkward, often funny, fallout of a life gone offscript. It captures the 'Sideways' essence of a man who dismantles his own life and is then forced to sift through the wreckage.
