Jonah Hill's journey to breaking stereotypes in Hollywood

People are overlooked for a variety of biased reasons and perceived flaws. Age, appearance, personality, Bill James, and mathematics cut straight through that. That's Jonah Hill and his Academy Award-nominated role as Peter Brand in 2011's Moneyball. And he's right in the middle of explaining to Brad Pitt's Billy Bean how he can help the athletics find the value of players that nobody else can see. It's pretty ironic because Hill's performance in the part would also help Hollywood and the whole world find overlooked value in a player that no one else seemed to be able to see, namely Jonah Hill. Does Pete really need to be here? Yes, he does. After developing a small following as a playwright in college, Jonah Hill decided he wanted to be an actor. Performing at open mic nights, he became friends with Dustin Hoffman's children, Jake and Becky, who eventually introduced the funny man to Hoffman himself. Hill made a CD of prank calls to amuse Hoffman, who then asked Hill to prank some of his friends. According to Hill, I had this bit where I'd phone people, pretend to be a celebrity's assistant, and ask for outlandish things. Hoffman would then later invite Hill to audition for a small role in David O. Russell's 2004 black comedy, I Heart Huckabees. And it would be in that movie that Hill would make his big screen debut. And things would take off pretty quickly for him from there. His next part would be a brief role in Judd Apatow's The 40-Year-Old Virgin, where he would share the screen with Steve Carell. I'm just trying to get these shoes back to my house so I can wear them. He would then follow that up with a slew of appearances over the next few years in studio comedies like Grandma's Boy, Click, Accepted, and Knocked Up. Ask me about my wiener! In most of the movies he made during this period, Hill filled the role of the stereotypical funny fat sidekick, a staple of raunchy comedies, at least since John Belushi's wild turn as Bluto Blutarsky in 1978's Animal House. Guys like John Candy, Dom DeLuise, and Chris Farley became comic superstars playing similar parts. Hill certainly put his own foul-mouthed, neurotic spin on the trope, but he was nonetheless usually confined to those sorts of roles. If I go in there and see sprinkled on the toilet seat, I'm going to lose my mind. Then in 2007, Seth Rogen and Evan Goldberg cast him as Seth alongside Michael Cera's Evan in their teen coming of age comedy Superbad. It was still a funny fat sidekick role in a raunchy comedy, but it was a co-lead, and the movie gave Hill some legitimate emotional beats to play. Audiences and critics took note. The movie was a massive hit. Hill was widely praised for his acting, and the role would become his breakout performance. You don't want girls thinking that you suck and, OK? Over the next few years, he would continue to make appearances in comedies like Forgetting Sarah Marshall and Get Him to the Greek, and would lend his voice to animated comedies like How to Train Your Dragon and Megamind. Renting a bouncy house? Cheeks don't have bouncy houses. They like clowns. Ow. Oh. But as the actor would later explain, behind the scenes, he was growing bored of repeatedly playing the same type of comedic sidekick roles. In his own words, doing the same thing over and over again is as boring to do as it's boring to watch. Looking to expand his dramatic horizons, Hill would turn down one of the lead roles in 2009's mega hit, The Hangover, and declined to play Shia LaBeouf's sidekick in 2009's Transformers, Revenge of the Fallen. Passing on parts in what would be two of the year's highest grossing films was risky. But Hill would later say, they were both really big decisions and ones that most people didn't understand. I knew I could be a dramatic actor, but I also knew I couldn't go from Superbad to Schindler's List. Then, in December of 2009, Bennett Miller was hired to replace director Steven Soderbergh on an adaptation of Michael Lewis's bestselling biography of Oakland A's general manager Billy Beane. Soderbergh's departure caused actor and comedian Dimitri Martin, who had been cast in the role that would eventually be renamed Peter Brand, to also drop out of the film. Miller offered the part to Hill, who leapt at the chance to play serious dramatic scenes against Pitt. Pack your bags. I just bought you from the Cleveland Indians. Despite his dramatic aspirations, the casting of Hill was initially perceived as a stunt to get young audiences into the film. And in all fairness, that skepticism wasn't totally out of left field. Hill himself has discussed how difficult it was to get a movie like Moneyball through the studio system, and his casting would provide certain advantages with a certain demographic. The studio forced him on us. Yeah, it was a very, yeah. It was stunt casting, and we made it work, though, I think. We got around. They did their best with what they had, and I just was grateful to be there, you know? Further fueling doubts was the simple fact that making a leap from comedic to dramatic acting is a career move many performers had tried before, and it didn't always work out so hot. On one hand, Tom Hanks was able to effortlessly transition from raunchy comedies like Bachelor Party to dramas like Saving Private Ryan and Apollo 13. And despite initially being famous for his absurd characters on the comedy variety show In Living Color and in movies like Ace Ventura Pet Detective, Jim Carrey was embraced by audiences for his serious tone performances in films like The Truman Show and Man on the Moon. That being said, examples to the contrary are far more common. Vince Vaughn's attempt at a dramatic turn in 1998's Psycho remake resulted in a stilted performance and a dud at the box office. Similarly, Unembraced by the Public, where Chevy Chase's 1992 turn in Memoirs of an Invisible Man, Mike Myers' awkward go in 1998's 54, Nick Kroll's forgettable performance in 2022's Don't Worry Darling, and so much more. Moneyball, however, was a huge success, And Hill's work earned both critical acclaim and an Academy Award nomination for Best Supporting Actor. The experience only made him more determined to build out his dramatic resume. Reflecting on his comedic acting career years later, Hill would explain, it's just not as inspiring to me anymore as an artist. I love doing it, but it really is exciting after Moneyball to have that taste for something different. Beyond being more creatively fulfilling, the dramatic success would completely change the trajectory of Hill's career. The following year, he would make a brief appearance in Quentin Tarantino's Django Unchained, a role that was originally planned to be larger, but had to be cut down due to conflicts with Hill's schedule. And in 2013, Hill would play Donny Azoff alongside Leonardo DiCaprio's Jordan Belfort in Martin Scorsese's 2013 drama, The Wolf of Wall Street. Steve Madden, Steve. But while DiCaprio took home $10 million for his work on the film, Hill was paid just $60,000. Despite the discrepancy, Hill told his agents, fax him the papers tonight. I want to sign them tonight before they change their mind. The actor would later explain, I would sell my house and give him all my money to work for Scorsese. This isn't what you make money for. You do 22 Jump Street or you do other things and you can pay your rent. I would have done anything in the world. I would do it again in a second. His performance would earn him his second Academy Award nomination for Best Supporting Actor. As he moved further away from the stereotypical roles he used to be trapped in, Hill underscored his transformation by losing the weight that led to such castings in the first place. In 2018, he would recall, I became famous in my late teens and then spent most of my young adult life listening to people say that I was fat and gross and unattractive. With his public image and his position in the industry vastly changed, Hill stepped behind the camera in 2018, making his directorial debut on the coming-of-age comedy drama, Mid-90s. The film was met with generally positive reviews, and Hill would tell NPR, my whole dream, my whole life, was to be a writer-director. I fell into this 15-year acting career where I got to learn from a lot of my heroes, and it's something I have wanted to do and would have done sooner. It's just that you only get one chance to make your first film. In the years since Moneyball, Hill has regularly worked with other auteur filmmakers, including Gus Van Sant, the Coen brothers, and Harmony Korine. And he's currently slated to star as Grateful Dead frontman Jerry Garcia in a biopic to be directed by Scorsese. But as rare as it is for comedic actors to so successfully make the transition, what Hill has found for himself is rarer still. Because unlike someone like Tom Hanks, who greatly reduced his comedic output after making his mark in dramas, Hill never stopped making comedies. In 2012, he teamed up with Channing Tatum for the surprise hit comedy 21 Jump Street, which Hill himself co-wrote and executive produced. In the subsequent years, he would continue to appear regularly in comedic parts, only, unlike in the period of his career before Moneyball, Hill can now do comedy without always being typecast in the same kind of role. Alongside his hard-earned dramatic credibility, it makes him a very unique kind of actor with a very rare sort of flexibility. And it all happened because Hill saw himself as an artist capable of meaningful work, and not just a paycheck player that made it all happen. Today, Jonah Hill can bounce back and forth between different types of films and different types of roles, simultaneously a beloved funnyman and a respected serious actor. Hollywood is finally playing cinematic moneyball and getting maximum value out of Jonah Hill. And we think Billy Beane would probably love that. How can you not be romantic about baseball?