To date, Alexander Payne’s films — Citizen Ruth, Election, About Schmidt, Sideways, The Descendants, Nebraska, and Downsizing — have been nominated for 19 Academy Awards and eight Golden Globes. While he would eventually win the Best Adapted Screenplay Oscar for both Sideways and The Descendants, Election earned him his first Oscar nomination for Best Adapted Screenplay. He says he gets the most compliments from movie lovers about the 1999 dark comedy that starred Reese Witherspoon as high school senior Tracy Flick. 
Over two decades later, author Tom Perrotta released a sequel: Tracy Flick Can’t Win. When asked if he would consider working on a follow-up film to Election, Alexander Payne said, “Oh yeah. It's possible — very possible. I'm interested in that world. I think there is more to say, but I'm not deep into deciding what that would look like yet. People have approached me over the years to turn Election into both a musical and an opera, if you can believe that.”
Election was a hit with critics but grossed only $17.2 million at the box office. However, it cemented Flick as a pop culture icon. Alexander Payne says, “Any film, including a retread, implies risk. And sometimes, people have been bitten in the heinie from attempting a remake or a retread. Still, other times they find a lot of success, and audience members also often are unoriginal in what they choose to see.”
While Flick has the potential to play a part in his future, Alexander Payne says he’s currently focused on finishing the editing of The Holdovers. That’s his latest dark comedy, about a disliked teacher — played by Sideways star Paul Giamatti — who stays on campus over winter break to chaperone the ragtag group of students who couldn’t travel home. “I am still going back and forth between Omaha, Nebraska, and Los Angeles to edit, and we just finished the very first cut of the movie. Editing is so interesting. No matter how many times you've done it and how skilled you think you are, every film is new, every cut is new, and it is an infinitely beautiful and mysterious process.” 
Tracy Flick Is Back!
“Tracy never went away, for me or the culture,” author Perrotta told Time. “That never happened with anything else I wrote.” And it’s painfully apparent in the sequel that Tracy Flick’s life trajectory didn’t go according to her plan either. Flick famously stated, “The weak are always trying to sabotage the strong,” Now, she’s an overworked assistant high school principal in suburban New Jersey, raising a daughter as a single mom. Perrotta said, “She’s a middle-aged person with regrets. She’s trying to figure out: ‘How did I get here when I expected to be somewhere else entirely?’” 
In the new book, Flick’s passion for winning is reignited when she learns that her boss is retiring, setting her sights on the top spot. “I didn’t think she had taken over the world. I’m much more interested, anyway, in thwarted ambition and midlife malaise than I am in people who are running the world,” Perrotta said. So to him, it was only natural that Flick “would end up in her old battleground, still fighting for these small prizes.” 
Alexander Payne and Reese Witherspoon Discuss Bringing Tracy Flick to Life On-Screen 
Alexander Payne never expected Tracy Flick to have such lasting appeal. “One never foresees that — one only hopes that,” he told Vanity Fair. “I wasn’t seeing it so much as a political metaphor. I just thought it was a fun little comedy. It has a good rhythm to it. Somehow the stars aligned to make a pretty decent little film.”
Perhaps he’s being a bit modest. The filmmaker coaxed amazingly nuanced performances from Witherspoon, Matthew Broderick, and Chris Klein in his first on-screen role. In addition, he spent time working with Witherspoon on the character’s accent. “He didn’t want it to be too Midwestern — too many round o’s, so we really worked on that. Also, the way she would pronounce certain words,” recalled Witherspoon. “What I love about working with Alexander is that he would use all these animal metaphors. He would be like, ‘This is like you’re in a National Geographic documentary, and you’re a panther, and you’re going down the hallway and going to pounce.’ And sure enough, you would move at a different cadence. And your body would move in a different rhythm when you had a different feeling. And it was really helpful as an actor. Not to think in terms of a person but in terms of animal behavior.”
Payne explained that Flick is “a person. A strong person with a strong personality. But that is how I see all the characters in my movies. They’re people. Because I have to understand them and see what makes them tick.”
Perhaps it should be no surprise that politicians are Election fans. “Barack Obama has told me twice that it is his favorite political movie,” shared Payne.