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Ranking the Films of Alexander Payne (Including ‘The Holdovers’)

From Citizen Ruth all the way up to The Holdovers, we’re ranking every feature film by acclaimed director Alexander Payne!

Alexander Payne at the London BFI Film Festival
Alexander Payne at the London BFI Film Festival. Credit: Shutterstock/ Loredana Sangiuliano

Who else saw The Holdovers over the holiday season and was just swept away by it? It is perfect viewing for a cozy day indoors, and it appears to be a hit with both audiences and critics alike. Alexander Payne, the director, is no stranger to films of a similar nature. He is the master of the “tragicomedy”, as his films do an excellent job of milking the hilarity out of the saddest characters and situations. He is a celebrated filmmaker whose films have garnered plenty of accolades, including 24 Oscar nominations. With The Holdovers fresh on everyone’s minds, let’s take a look at all eight of Alexander Payne’s feature-length films and rank them from worst to best!

8. Downsizing (2017)

Matt Damon and Kristen Wiig in Downsizing. Credit: Paramount Pictures

I have much praise to heap onto a majority of the films on this list, so this will be the sole negative entry. It follows a married couple, Paul and Audrey Safranek (played by Matt Damon and Kristen Wiig, respectively), who take part in a new scientific procedure that shrinks the entire human body down to mere inches in an effort to conserve natural resources. When Audrey gets cold feet and leaves Paul after his procedure has already been completed, Paul is left in the downsized community alone. There, he befriends his eccentric neighbor Dusan (Christoph Waltz) and outspoken political activist Ngoc Lan Tran (Hong Chau), who has been downsized by the government in an attempt to silence her.

Unfortunately, Downsizing is an absolute misfire that squanders an interesting premise and coasts along on a bloated runtime. Based on the intriguing setup alone, it sounds like it would be a slam dunk. But it hardly utilizes any of the humor that can be had with such a scenario. It’s a preachy film that does away with much of Payne’s sense of humor. It tries harder to make a statement than it does to create likable, sympathetic characters, or even tell a compelling story. Perhaps Payne’s most ambitious film, and one big swing and a miss.

7. The Descendants (2011)

George Clooney, Shailene Woodley, Amare Miller, and Nick Krause in The Descendants. Credit: Fox Searchlight Pictures

George Clooney takes center stage in this film about lawyer Matt King (Clooney), whose wife goes into a coma after a boating accident. Matt must step up and parent his two daughters that he has become distant from, as well as confront the man that his wife was having an affair with.

The quality gap between The Descendants and Downsizing is immense, and this a fine drama from Payne. It ranks low on my list for that reason though. It is primarily a drama with more sentimentality and less humor than his other films. Clooney delivers a stellar performance, but the film, while worth checking out, does not have as much of Payne’s signature darkly comedic flavor as I would like.

6. Election (1999)

Matthew Broderick and Reese Witherspoon in Election. Credit: Paramount Pictures

We transition from arguably Payne’s most dramatic outing to his most outwardly comedic. Election follows high school teacher Jim McAllister (Matthew Broderick) and his efforts to thwart over-achieving class presidential candidate Tracy Flick’s (Reese Witherspoon) campaign by convincing the dimwitted star player of the football team to run against her.

It is a witty satire with an absolutely fierce comedic turn from Witherspoon, although its satirical edge and dark humor are outdone by an earlier film of his that we will get to later on down the list. That said, Election is a fun experience, and one of the best films to introduce someone to Payne’s work with.

5. About Schmidt (2002)

Jack Nicholson in About Schmidt. Credit: New Line Cinema

Based on the novel of the same name and featuring one of Jack Nicholson’s best late-career performances, About Schmidt follows Warren Schmidt (Nicholson), a recently retired (and recently widowed) man who decides to take his RV and drive across the country to attend the wedding of his estranged daughter.

Aided by two fantastic supporting roles from Kathy Bates and Dermot Mulroney, Nicholson shines here in a much more subdued role than normal. He plays an old curmudgeon who (like so many of Payne’s protagonists) goes through a cathartic transformation as a result of the misery he has been dealt. Road trip character studies seem to be Payne’s bread and butter, and this is a fine addition to that sub-genre.

4. Citizen Ruth (1996)

Laura Dern and Mary Kay Place in Citizen Ruth. Credit: Miramax Films

Payne’s first and potentially most underrated feature follows Ruth Stoops (Laura Dern), a rebellious young woman who gets pregnant and finds herself at the center of the abortion debate as pro-life and pro-choice activists pull her back and forth in a game of political tug-o-war.

The superior satire that I mentioned earlier, Citizen Ruth does an excellent job taking jabs at political opportunism. The film demonstrates each side as equally conniving as they treat Ruth as a mere pawn to further their agendas. It acts as a commentary on politics as a whole in the way that the endless bickering between the two sides overshadows Ruth herself, the person at the heart of the conflict. It is also a relentlessly funny film with a fantastic performance from Dern.

3. The Holdovers (2023)

Paul Giamatti and Dominic Sessa in The Holdovers. Credit: Focus Features

Payne’s newest film ranks high among an already impressive body of work. Set in the empty hallways of a prep school during the 1970 winter holiday, it centers on the unlikely comradery that forms between the three people stuck at the school over the break: cranky history teacher Paul Hunham (Paul Giamatti), troublemaker student Angus Tully (Dominic Sessa), and the school’s head cook, Mary Lamb (Da’Vine Joy Randolph).

From its vintage aesthetic choices, Christmas-heavy soundtrack, and touching story, The Holdovers is a warm blanket of a film that is among 2023’s most heartfelt and hilarious feel-good experiences. Giamatti and Sessa have pitch-perfect chemistry throughout, and it’s an absolute joy seeing their hostile relationship grow into something much more friendly as the film goes on. It does end on a bit of a predictable note, but the overall experience is a joy to watch regardless. I anticipate this becoming a classic in time.

2. Nebraska (2013)

Bruce Dern and Will Forte in Nebraska. Credit: Paramount Pictures

Shot entirely in black and white, Nebraska sees David Grant (Will Forte) agree to take his father, Woody (Bruce Dern), on a road trip to the titular state to claim the winnings from a scam sweepstakes prize that Woody is convinced he has won. Past indiscretions are revealed and old wounds are reopened as the father and son come across estranged family and old figures from Woody’s past when their journey takes them back to his hometown.

Nebraska perhaps has the biggest heart of any of Payne’s films, and Bruce Dern contributes so much to an already stellar script in his portrayal of Woody. The comedy is drier and more understated in this one, but the deadpan delivery of the humor fits perfectly with the overall tone of the film. The final moments are some of the most heartwarming scenes of Payne’s career, and the movie as a whole is one of his greatest triumphs.

1. Sideways (2004)

Paul Giamatti and Thomas Haden Church in Sideways. Credit: Fox Searchlight Pictures

Perhaps still his most iconic work (debatable given how big of a hit The Holdovers has become), Sideways follows Miles Raymond (Paul Giamatti), a struggling writer, divorcee, and wine enthusiast, who joins his friend Jack Cole (Thomas Haden Church) on a road trip (sensing a pattern yet?) through California wine country. Jack is soon to be married and is using the trip as an excuse to have one last fling before his impending nuptials, much to Miles’ annoyance. Miles cannot shake the lingering feelings for his ex-wife, all the while waiting with bated breath to hear back from his agent who’s been shopping his new book around to potential publishers.

Somewhat comparable to Swingers before it, Sideways is the film that does the most excellent job of blending Payne’s sense of humor with genuine drama. The characters are honest, real, and lived in, with writing and performances that work together beautifully in bringing them to life. The film has arguably the best pairing of actors in any of Payne’s films with Giamatti and Church, who bounce wonderfully off one another.

It’s endlessly re-watchable, easily his funniest film, and a poignant character journey through the California countryside. Sideways isn’t just my favorite Alexander Payne movie. It’s simply one of my favorite movies.

And we’re still not drinking any [EXPLETIVE] Merlot!

An Impressive Filmography

It’s clear to see why Payne is such a respected voice in the business. Admittedly, he sticks to formulas, but that’s hardly an issue when the execution is so consistently strong. Each film of his (arguably even his singular dud) has a unique voice, clever writing, and dense characters. He is among the chief voices keeping old school “they just don’t make them like this anymore” cinema alive. As long as he continues putting out new films, I’ll be there at the theater with my ticket in hand.

Written By

23 year old from Minnesota, soon to graduate from Metropolitan State University with a BA in Technical Communications and Professional Writing. Full time lover of films and part time builder and enthusiast of Lego, I aspire to someday cultivate a career where I can spill the various thoughts that flood my head about these passions to a vast audience!

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