Ever since I first saw the dark comedy Election in 1999, I’ve followed Alexander Payne closely through the highs of About Schmidt and Sideways to the lows of Downsizing. He’s a fantastic writer and director who tells captivating human stories packed with complex characters, strong writing, and an emphasis on relationships, the intricacies of love, marriage, friendship, and generational conflicts.
In other words, this Friday, I’m heading to the theater to watch The Holdovers. In case you’re not familiar with Payne’s work, I’ve compiled a list of the five best Alexander Payne movies. Surprisingly, the man has only directed nine films (including The Holdovers) alongside a handful of TV episodes and short movies. Slim pickings, for sure, but nearly all of his pictures are worthy of a positive review.
About Schmidt (2002)
In this dark comedy, Jack Nicholson delivers a tour de force performance as Warren Schmidt, a recently retired insurance executive who embarks on a transformative journey in his RV following the loss of his wife. Along the way, he encounters a cast of eccentric characters, each encounter prompting a profound reexamination of his life and the complex dynamics with his late wife and estranged daughter.
Nicholson takes the cake here, but the intelligent, thought-provoking script written by Payne, Louis Begley, and Jim Taylor touches on everything from aging to regret, resulting in an emotionally satisfying, even poignant, motion picture experience.
Sure, the pacing is a little slow, and the tone is somber. Still, those willing to take the journey will enjoy a cinematic gem containing profound storytelling, incredible acting, and touching drama.
Election (1999)
I can’t believe Election came out in 1999—nearly 25 years ago! My friends and I went to the theater to see this flick expecting something similar to a John Hughes comedy. Plus, we thought Reese Witherspoon was hot. Instead, we got a sharp satire about political corruption, power, and ambition, albeit set in a high school environment. My buddies were (mostly) disappointed while I walked away enamored by this wholly original picture. It was just … different.
Multiple viewings only increased my appreciation. Now, it’s one of those movies I obsessively try to show everyone—often with extremely mixed results.
Witherspoon and Matthew Broderick shine in their respective roles, the former delivering a skillful performance as the ambitious but vulnerable and insecure Tracy Flick. You can’t take your eyes off her.
Power struggles, moral dilemmas, flawed characters, and an overabundance of dark humor make Election one of the great films of the 1990s.
Sideways (2004)
Who knew a film about wine could be so … fun? Smart, poignant, and also incredibly funny—and very adult—Sideways follows two men, Miles (Paul Giamatti, in a star-making performance) and Jack (scene-stealer Thomas Haden Church), as they journey to wine country for one last hurrah before the latter gets married. En route, they shack up with two women, Maya (Virginia Madsen) and Stephanie (an excellent Sandra Oh), who throws a wrench in their plans.
Once again, Payne strives for realism, crafting uniquely flawed but relatable characters viewers can connect with on a deeper level. I’ve dropped the word “complex” a lot, but that’s the best way to describe Payne’s characters. Miles is a wine connoisseur who is introverted, neurotic, and struggling with his failed marriage and writing career. In contrast, Jack is an extroverted womanizer who seeks adventure and excitement. Somehow, you identify with both—they’re endearing despite their imperfections.
Moreover, the film looks great thanks to Phedon Papamichael’s beautiful cinematography, and Payne’s direction allows the story to unfold naturally. Amazing stuff.
Nebraska (2013)
Emotionally resonant and undeniably heartwarming, Nebraska is perhaps Payne’s most sentimental and accessible work. Starring the great Bruce Dern, Will Forte, June Squibb, and Bob Odenkirk, the pic follows a father and son as they travel to Lincoln, Nebraska, to collect a major award. Like About Schmidt, their journey brings our heroes across a slew of colorful characters and gives them time to reflect upon their lives.
Payne offers a commentary on the unattainable American Dream and views American culture through the eyes of an atypical family dealing with common challenges and conflicts that arise over time. The road trip serves as a catalyst for understanding and reconciliation as they find opportunities to connect and resolve their differences.
There aren’t many films that touch the soul like Nebraska.
The Descendants (2011)
I love, love, love this movie. George Clooney delivers the performance of his career as Matt King, a businessman who discovers his wife is cheating on him. The twist? She’s in a coma sustained during a boating accident. You can only imagine the emotional conundrum this situation presents.
On top of this, Matt must contend with his two rebellious daughters while also facing the responsibility of deciding on the sale of a valuable piece of family-owned land in Hawaii. Payne delivers his customary batch of clever dialogue, wit, and uniquely defined characters but touches on darker themes of grief, loss, death, and familial struggles. You laugh, you cry, etc.
The Descendants hits hard and perfectly balances touching comedy and thought-provoking drama with tremendously satisfying results. Out of Payne’s impeccable work, this is the one I return to most.
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