Every Alexander Payne film, ranked

Reese Witherspoon in Election (Paramount Pictures), Paul Giamatti in Sideways (Searchlight Pictures), George Clooney in The Descendants (Searchlight Pictures), Matt Damon in Downsizing (Paramount Pictures)
Reese Witherspoon in Election (Paramount Pictures), Paul Giamatti in Sideways (Searchlight Pictures), George Clooney in The Descendants (Searchlight Pictures), Matt Damon in Downsizing (Paramount Pictures)
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Reese Witherspoon in Election (Paramount Pictures), Paul Giamatti in Sideways (Searchlight Pictures), George Clooney in The Descendants (Searchlight Pictures), Matt Damon in Downsizing (Paramount Pictures)

It’s been six years since Alexander Payne released his last film, Downsizing, to mixed reviews. Now he’s back with The Holdovers, which is being hailed as a return to form by those who’ve caught it on the festival circuit. The film reunites Payne with Sideways star Paul Giamatti, who plays a curmudgeonly professor at a prestigious prep school forced to spend an eventful winter break with a troubled student (Dominic Sessa) and the school’s chef (Da’Vine Joy Randolph). The film arrives in theaters on October 27.

In the meantime, we decided to take this opportunity to look back on the writer-director’s work through the years. Although his filmography only consists of seven films (not including The Holdovers), his movies have earned a total of 19 Academy Award nominations, and racked up two wins, for the screenplays for Sideways and The Descendants. Here’s how Payne’s films stack up.

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In the mid-1990s, a film like Citizen Ruth could be written off as a jaunty farce (witness the bouncy, lighthearted tone of the original trailer) about the silly extremists ineffectually battling over the issue of abortion. That doesn’t play so well in 2023, in the wake of a partisan Supreme Court dismantling Roe v. Wade and the winning side embarking on a vindictive victory lap across multiple states. The film’s refusal to take sides no longer feels as amusing, bold, or clever as it did when it first came out. Now, it feels more like a cop-out. Laura Dern’s performance as Ruth, a dim-witted drug addict who finds out she’s pregnant, is just this side of camp, which suits the tone just fine. She soon becomes a target of exploitation for both anti-abortion and pro-choice advocates, who are depicted as equally kooky and exaggerated for comic effect. Each side sees Ruth as a pawn to be exploited in the interest of their own causes. While Citizen Ruth hasn’t aged as well as Payne’s more restrained work, it might make you nostalgic for a time when the abortion debate was something audiences could laugh about. On a technical level, though, it remains an impressive debut for a filmmaker who would continue to walk the line between comical farce and topical drama throughout his career.

6. Downsizing (2017)

Downsizing begins with an intriguing premise—a Norwegian scientist develops a method for shrinking humans to five inches as a humane way to mitigate overpopulation and avert environmental disaster. Enter Matt Damon’s character Paul Safranek, an ordinary guy who buys into the marketing pitch that downsizing is an opportunity to live the life of luxury he’s always dreamed of but could never afford. Had Payne contained the story to focus on the inherent tension between these two ideas the film might have been more successful. Instead, he attempts to extrapolate every far-reaching consequence the discovery might have on life as we know it, while skimming over the nuts and bolts of how the small world actually works (like, how do they make nuts and bolts?). Damon and his co-stars, especially Christoph Waltz and Hong Chau, give their all to a script filled with too many ideas and not enough space to explore them.

5. The Descendants (2011)

Payne adapted the Oscar-winning script for The Descendants, with help from co-writers Nat Faxon and Jim Rash, from the novel by Kaui Hart Hemmings. George Clooney was nominated for an Oscar for his layered performance as Matt King, an attorney trying to keep his family’s vast Hawaiian estate intact while also dealing with the fallout from a boating accident that left his wife in a coma. As he tends to do in his films, Payne makes great use of the story’s setting and its thematic link to the characters and their relationships to each other. Just as Hawaii may be viewed as a pristine paradise by outsiders, an outwardly happy family may seem less so upon further inspection. The characters are forced to face the messy consequences of their own actions as the cracks in the foundation are laid bare. By this point in his career, Payne had perfected his own particular blend of pathos and comedy, but his ultimate goal isn’t to make you cry or laugh—it’s to make you sympathize with his rich, multi-dimensional, and painfully human characters.

4. About Schmidt (2002)

Together with frequent writing collaborator Jim Taylor, Payne crafted this heartbreaking, intimate portrait of a man looking for meaning near the end of his life, and gave Jack Nicholson the gift of a complex character he could really sink his teeth into. About Schmidt employs many of Payne’s favorite storytelling elements—lost and lonely middle-aged guys, rambling road trips, bleak Midwestern landscapes—to make a point about what might or might not be left to reap from a life in which nothing has ever been sown. Following his retirement after 40 years as an insurance actuary, Nicholson’s Warren Schmidt moves from one unfulfilling existence to another, forced to spend time at home with his wife Helen (June Squibb), who controls his every move. We know all about Schmidt’s seething resentments through the device of narrated letters written to an African child he sponsored on a whim. When Helen unexpectedly dies, Warren becomes unmoored, knowing from his experience as an actuary that his days are numbered, yet unable to make the best of them. As he takes to the road in the RV Helen bought before her death, Payne’s unblinking eye captures the mundane and metaphoric landscape that informs the character’s caustic worldview.

3. Nebraska (2013)

After films against the golden backdrop of California wine country and the tropical environs of Hawaii, Payne returned to his roots for Nebraska, a stark, black-and-white road trip through a gloomy Midwest. Bruce Dern delivers a triumphant, late-career performance as Woody Grant, a cranky old coot on the verge of senility who receives a letter from a Publisher’s Clearing House-type operation and believes he has won a million-dollar sweepstakes prize. Though his family tries to convince him it’s a scam, he’s determined to get to Nebraska to claim his winnings, even if it means walking there from Montana. Ultimately, his son (played by a deceptively affable Will Forte) agrees to take Woody on a road trip that involves passing through his father’s old hometown, where his troubled past awaits a reckoning. This was Payne’s fifth film, and it received six Oscar nominations, the most of any of his projects to date (it didn’t win any statuettes, though). It was also his first time directing a film he didn’t write or co-write (The Holdovers is the second).

2. Election (1999)

Election was only Payne’s second film, and we still consider it one of his best. This witty and darkly funny political satire set in a high school takes its cues from the Tom Perrotta novel that inspired it, which was meant to echo the 1992 presidential race. Though Payne made a few tweaks that helped it feel more timeless, the basic structure is the same: it centers on a student council race that overachiever Tracy Flick (a perfectly cast Reese Witherspoon) is determined to win, until the election becomes complicated by the candidacies of a popular football player (Chris Klein) and his bitter younger sister Tammy (Jessica Campbell). The villain in this divisive student-council race isn’t the admittedly insufferable Tracy, or any of the other student candidates; it’s Matthew Broderick’s Mr. McAllister, who can’t resist personally interfering in the supposedly student-run election when it looks like things might be going in a direction he doesn’t like. Do the skills required to win an election translate to good governance? What principles are we willing to compromise in the pursuit of furthering what we believe to be a just society? Who gets to decide that anyway? The film asks a lot of questions, but lets the audience decide how to answer them.

1. Sideways (2004)

Alexander Payne had made a name for himself among a certain set of cinema aficionados with his first three films, but it was the tour de force dramedy Sideways that really brought him to the attention of the film community at large, not to mention causing Merlot sales to plummet. Adapted from the Rex Pickett novel of the same name, it stars Paul Giamatti and Thomas Haden Church as unlikely best friends on a tour of central California’s wine country. Much of the film’s comedy, and drama, comes from the disconnect between the characters of Miles (Giamatti) and Jack (Haden Church), who have very different ideas of what they want out of the weekend. When they pick up a pair of women, played by Sandra Oh and Virginia Madsen, their individual approaches to wooing them are indicative of their fatal blind spots. Payne knows exactly what pressure points to touch on these characters to make them act out, as the sun-kissed California haze casts a dreamy glow over everything. It’s as revelatory as a vintage pinot noir.

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