What a strange career Jesse Eisenberg has had. After launching onto people’s radar with “The Squid and the Whale,” he has regularly dabbled back and forth between mainstream and indie cinema. Anchoring everything from “Rio” to “Night Moves” to “30 Minutes or Less” to “Now You See Me,” Eisenberg has gone all over the place looking to carve out his own path in Hollywood. Now, his unpredictable career encompasses writing and directing movies. His second feature-length directorial effort, “A Real Pain,” is picking up award-season buzz after its prolific Sundance launch, which has only continued through Telluride, NYFF, and now onto its theatrical release. This film could bring Eisenberg back to the Oscars nearly fifteen years after the role that forever changed his career: Mark Zuckerberg in “The Social Network.”
Eisenberg would be the first to admit that he filled a particular type in Hollywood, especially in his younger years. He was a taller, skinny white guy with a good sense of comedic timing that could also believably ace dramatic flourishes. If you needed an actor to play a total contrast to Woody Harrelson in “Zombieland,” he was your guy to call. When “Adventureland” required a reedy 18-year-old protagonist, Eisenberg could step up to the plate. Eisenberg was able to parlay roles that took advantage of his physicality to demonstrate his chops as an actor.
Hollywood’s restrictive ideas of what makes a “proper” male lead meant that Eisenberg wasn’t going to anchor a Marvel movie or be in a rom-com lead anytime soon. He leaned into that and produced several memorable turns in successful films, including his most beloved turn as Zuckerberg in “The Social Network.” Eisenberg had the physical resemblance and age of the Facebook entrepreneur down pat, making him an obvious choice for the role by director David Fincher. More importantly, though, Eisenberg could also play this guy as an aloof, egotistical soul with hints of internal torment. You can see flickers of pained humanity within Eisenberg’s pupils without the actor sacrificing the more unlikeable parts of Zuckerberg in the process.
After “The Social Network,” Eisenberg did not score another Oscar nomination, and his foray into anything remotely resembling Oscar-friendly fare was anchoring a pair of Woody Allen movies. All of this was building up to Eisenberg’s “returning” to the world of directing. Granted, the word returning must be used loosely here since Eisenberg’s only pre-2022 directorial effort was a short film entitled “Becoming a Werewolf” on the DVD bonus features for “Cursed.” Still, helming even something that slim early into his career made it clear he had greater aspirations than “30 Minutes or Less,” though. He wanted to work behind the camera, not just in front of it.
This resulted in his feature-length directorial debut, “When You Finish Saving The World,” which premiered at the 2022 Sundance Film Festival before getting quietly dropped to the general public in January 2023. The film received mixed reviews, which included some passionate defenders, but mostly elicited a shrug from people. At this juncture, Eisenberg’s directorial career didn’t seem dead. However, it appeared to be far from producing anything that would become an awards season juggernaut. A24 had so little faith in “When You Finish Saving The World’s” Oscar chances that no real For Your Consideration campaign was undertaken.
Two years later, Eisenberg returned to Sundance with “A Real Pain,” which saw him directing and starring in his own movie this time. This two-hander between him and “Succession” Emmy Award-winner Kieran Culkin instantly received significantly more positive buzz than “When You Finish Saving The World.” The Searchlight Picture release has proven to be critically acclaimed enough for nearly all of 2024 to become a contender for Best Picture, Best Actor, Best Supporting Actor, and Best Original Screenplay at the Oscars. That’s quite a turnaround from Eisenberg’s feature-length debut, which quickly faded from the pop culture consciousness.
If Eisenberg scores an Oscar nomination for his screenwriting, he’ll enter a rarified breed of actors who are also Oscar-nominated screenwriters. Greta Gerwig and Jordan Peele are two of the most famous modern examples of this phenomenon, but throughout the history of cinema, there are countless other impressive examples. John Huston scored a Best Adapted Screenplay nomination for “The Treasure of the Sierra Madre” in 1948. Bradley Cooper was nominated for screenwriting Oscars on two separate occasions for “A Star Is Born” and “Maestro.” George Clooney has also garnered two Oscar nominations for screenplay with his directorial efforts, “Good Night, and Good Luck” and “The Ides of March.”
This is a rich history that Eisenberg has a good shot at entering. It doesn’t hurt that the Academy has been especially enthusiastic about nominating actors-turned-screenwriters in the last fifteen years. That trajectory could help ensure Eisenberg has a seat in a crowded Best Original Screenplay field. However, even just getting buzz for this category feels like it’s from another planet compared to the places Eisenberg’s career has previously been. Nobody watching “Adventureland” all those years ago would have imagined this is where Eisenberg was headed as an artist. And he may even be able to ride the wave of “A Real Pain’s” success to a second nomination for Best Actor if Academy voters love the film enough.
This is an unexpected detour reminiscent of other actors-turned-artists, such as Ben Affleck, who decided to make the kinds of movies he loved to watch and act in. If Hollywood wasn’t going to bring the juicy roles to their doors, then these actors would create them. Granted, Eisenberg is (wisely) still willing to play the mainstream Hollywood ball. After all, he’s currently shooting “Now You See Me 3” as his first on-camera role after “A Real Pain.” And yet, throughout his career, he has shown that he’s capable of far more than that. Just look at his outstanding performance in “The Social Network.” Even when his feature-length directorial career seemed disappointing, Eisenberg has come back swinging with a critically acclaimed follow-up that could land him further Oscar nominations and maybe even wins for him and Culkin. That’s the kind of unpredictability that leads your career to unexpected places, and expect to see Eisenberg’s career go to bigger and better places from here.
Have you seen “A Real Pain” yet? If so, how many Oscar nominations do you think it will receive and how many will be for Jesse Eisenberg? Please let us know in the comments below or on Next Best Picture’s X account, and be sure to check out Next Best Picture’s latest Oscar predictions here.
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