After seeing his status ascend to new heights following his role in Superbad, many comedy fans probably thought they could map out the trajectory of Jonah Hill’s career. Since the days of W.C. Fields and Lou Costello, the careers of funny big men have had a similar shape. John Belushi, Chris Farley, Kevin James, Josh Gad: there is a long list of plus-sized actors who have leaned on physical comedy to propel them to stardom, always game to play the chaotic sidekick or the goofy best friend.

However, Jonah Hill has rejected the playbook that was pre-written for him after Superbad and built a career unlike any actor Hollywood has ever seen by turning down typecast roles and specifically using key roles to springboard him to wider possibilities - thus setting him up as a serious dramatic actor, a major creative force, and an unexpected streetwear ambassador.

It wasn’t luck either that took him from bit player in The 40-Year Old Virgin to preparing to star opposite Emma Stone in the upcoming Cary Fukunaga-directed series Maniac. Hill has balanced careful planning and taken calculated risks to great effect.

While on the surface level his success may only seem like a roadmap for those wanting to navigate a career in Hollywood, a closer examination of Hill’s career up until this point reveals universal truths and tips for anyone wanting to navigate a life in the arts.

Build a Base

You can’t take risks until you have a reputation. Until people know who you are, it is difficult to start defying expectations. It is useful to think of Jonah Hill’s career in two phases: before and after 2011. In 2011, Hill received his first Oscar nomination for Moneyball. To get to that point, Hill had to establish himself in Hollywood, and as such, the first years of his career read like that of any big time funnyman.

Hill’s early career is defined by his relationship with Judd Apatow. The stable of actors that Apatow built, including Jason Segel, Paul Rudd, Seth Rogan, and Martin Starr would come to define comedy movies in the first decade of the 2000s. Hill’s films associated with Apatow in that era include The 40-Year-Old Virgin, Knocked Up, Superbad, Walk Hard, Forgetting Sarah Marshall, Funny People, and Get Him to the Greek. His other work during that period involves films more or less in the same spirit of Apatow productions, like Grandma’s Boy, Evan Almighty, and The Invention Of Lying as well as children’s movies like Horton Hears a Who!, How to Train Your Dragon, and Megamind.

Balancing foul-mouthed comedies with children’s voiceover is a common path for a comedic character actor, but Hill stood out in that familiar mode. Even when Hill was doing broader comedies, he was well received by critics.

Peter Travers praised Hill’s work in Superbad at Rolling Stone, writing that Hill and co-star Michael Cera, “deftly uncover two scared teens trying to hide their feelings.”

The Atlantic’s Christopher Orr had similar praise while pointing out the obvious limits of his roles: “Jonah Hill, who played one of Seth Rogen’s stoner buddies in Knocked Up, is as good as Seth, the loud-mouthed fat-guy character who will be familiar to anyone who’s seen an American comedy in the last thirty years.”

It’s hard to say Hill got tired of being a funnyman. Many actors start chafing under one funny sidekick role after another, but Hill is still taking comedy roles today. He also shows no signs of slowing after more than a decade in comedy. Hill was able to diversify his acting portfolio before he started projecting bitterness. However, around the time that Hill started to branch out from the Apatow camp, he began to hint that he wanted more out of his career. It was evident that Hill had more range than what he was being offered, and it was only a matter of finding the right opportunity for a career shift.

In an interview with Vanity Fair’s Mike Ryan, Hill bristled when Ryan compared his upcoming role in an indie dramedy with an SNL character he had played previously. He said, “the SNL guy was loud and Cyrus is very quiet and manipulative...I don’t see it, but more power to you. One is an annoying SNL character and one’s a character I worked really hard on in the movie.” Hill seemed to realize in an instant that this comment might be taken the wrong way. He was quick to add, “I never go, ‘Oh, man, I've done all of these comedies, I need people to take me seriously.’ It's never like that. You just always want to do things that interest you and you think will be good. Also, you really want to try and challenge yourself to do something different.”

From rare comments like these, it was clear that Hill knew that the Apatow era wouldn’t last forever, and that he wanted to be known as something more than being a funny sidekick. Before the Apatow crew’s day in the sun was over, Hill started looking in other directions. While Hill has continued to work with his comedy cohort on projects like Sausage Party and This is the End, it was only a few years after becoming a household name that Hill looked for new avenues in his career.

Change Directions

Though the biggest risk with the biggest payoff of Hill’s career would be Moneyball, he actually set the stage for a career shift with a small indie movie the year before he signed on to the Bennett Miller prestige project. In 2010, Hill signed on to the aforementioned Duplass Brothers indie film, Cyrus. Alongside veteran character actors John C. Reilly and Marisa Tomei, Hill played a clingy son getting in the way of his potential stepdad’s romantic designs.

“Jonah was so eager and excited to do something different that we never had to push,” Mark Duplass said, describing preparations for Cyrus. “He was willing to try anything, to go anywhere. In the wrong hands, the role of Cyrus could have been a kitschy, over-the-top cornfet. Jonah just happens to have a big brain and an even bigger heart, and it was clear to everyone from day one that he was headed for big things.”

Cyrus didn’t break box office records or earn Hill Oscar buzz, but it did give him a crucial foothold in the dramatic world that would help him land the role of a lifetime. This seems to have been intentional on Hill’s part. Later in that Vanity Fair interview, he said, “I absolutely love the big, broader comedies that I get to be a part of and I also love something more small and grounded like Cyrus. [Points to the Cyrus movie poster] Look at that billing: Academy Award nominee [John C. Reilly], me, Academy Award winner [Marisa Tomei], Academy Award nominee [Catherine Keener]. It's crazy.”

Hill could already see where he wanted to go next.

Take Risks

"The most challenging scene I ever shot in my life was when Billy asks me to trade [first baseman Carlos] Pena and basically fire him. It's a 45-second scene, which is not long, but it's rare you get to see a character grow up in 45 seconds.”

This quote, from a 2011 interview with The Hollywood Reporter paints a picture of Hill embarking on an exciting and slightly terrifying new step in his career with Moneyball. Hill was up to the challenge. On the strength of Cyrus, star and producer, Brad Pitt, and director, Bennett Miller, agreed it was time to give Hill a shot at a more serious role. Miller was so impressed with Hill’s work in Cyrus and his thoughts on the role, he was ready to cast him without an audition. It was clear to Miller and Pitt that Hill would be up to the challenge.

Their faith proved to be well placed and Hill's words to Vanity Fair proved prophetic. His performance as Peter Brand in Moneyball earned him an Oscar nod and set the stage for a shift in his career.

Stay Hungry

After Moneyball, Hill could have rested on his Academy laurels, and waited for the next project to come to him. He also could have gone back to splitting his time between Apatow-style comedy and voiceover. Instead, he chose not to miss a beat, and started doggedly pursuing his next role.

The Oscar nomination put Hill in the running for other roles that would carry the same prestige as his work in Moneyball. But his next major role in Wolf of Wall Street didn’t just fall into his lap. Hill says that the role of Donnie Azoff in Wolf only came to him through persistence. It just so happened that he was in Mexico doing publicity for 21 Jump Street while Leonardo DiCaprio was promoting J. Edgar. Hill made sure to track down Leo and plead his case for why he should play Donnie. He even offered to take a pay cut, making just $60,000 for half a year of shooting.

His persistence paid off. With two prestige projects and two Oscar nominations under his belt following the success of Wolf of Wall Street, Hill had completed the difficult transition from comedic sidekick to serious character actor. Roles in Django Unchained, Hail, Caesar!, and the upcoming Harmony Korine project, The Beach Bum, have followed, and Hollywood’s perception of him has forever shifted.

If this were the limit of Hill’s career, it would be special, but it wouldn’t be unique. Steve Carell and Robin Williams have pulled off the funnyman to sad clown transformation with equal grace and greater accolades. It turns out that his time on Moneyball would have a greater impact on Hill than even he initially thought. Working with Brad Pitt would motivate him to take creative control of his career and starting driving the projects he signed on to.

Take Creative Control

In that Hollywood Reporter interview for Moneyball, Hill foreshadowed the next stage of his career. He spoke of his admiration for Brad Pitt not only as an actor but as a creator, saying, "I learned a tremendous amount from Brad, not specifically about acting on Moneyball, but by watching him produce and watching his commitment to this movie throughout so many incarnations, and just his advice about making interesting choices as an actor."

Moneyball didn’t just show Hill the importance of choosing good material, the project taught him about taking agency in the creation of your own material. After Moneyball, Hill would follow in Pitt’s footsteps, producing projects he is involved in and gaining a new measure of control in his projects.

Hill ensured that he had a producing title and story credit on 21 Jump Street. When he spoke to Collider on the set of 21 Jump Street, Hill explained that while the initial pitch for a remake “sound[ed] kind of stupid,” he felt that the idea of reliving high school carried a lot of potential. “Thinking you would get it right this time, and having all the answers, but immediately reverting back to the insecurities you had the first time around,” was something that stuck with him, and prompted him to seek a creative voice in the project. At the time he told Variety, “If I sign on, it’s because I really care and want to see it through.” He would also receive producing credits on The Sitter, 22 Jump Street, Sausage Party, and Why Him?

While some actors take on the producer title simply in hopes of a beefier paycheck, Hill saw it as a way to develop and execute his vision. Sony Pictures executive, Amy Pascal, spoke glowingly of how Hill approaches producing as a collaborative and creative process, “Jonah has this elegant and quiet way of helping without taking over. He is a perfectionist and a barometer of what is funny like no one I’ve ever seen before.”

Make Your Own Content

In time, Hill would take the push for creative control even further. In addition to producing, Hill began writing and directing work of his own. In 2011, Hill created the short lived animated TV show, Allen Gregory. The series followed the exploits of a precocious seven-year-old (voiced by Hill) and his two dads, Richard and Jeremy. Though the show was quickly cancelled, it gave Hill an opportunity to act as the primary creative voice on a project. Hill has story credits on Sausage Party and Why Him? as well.

Hill has also branched out into directing. He wrote and directed a short video for Sara Bareilles. He followed this up last year with a music video for the Danny Brown song, “Ain’t it Funny.” Hill will also be releasing his feature directing debut, Mid 90s, a coming of age comedy starring Katherine Waterston and ubiquitous indie presence Lucas Hedges.

Find New Outlets

Hill has even found ways to creatively shape his career even beyond the bounds of film and television. He's also emerged as a style icon in recent years; last year we called him “Hollywood’s Streetwear Ambassador.” He has been snapped wearing brands like Palace, Dime, Illegal Civilization, and Richardson. Hill found a way to turn his newfound hypebeast status into yet another creative win. He served as the spokesman for Palace’s 2016 collaboration with Reebok, working on one of the funniest ads the fashion world saw that year, once again flexing his creative chops.

Keep Going

This shift in Hill’s career of explicitly creating and shaping his content has had an undeniable impact on his acting career. Yes, Moneyball and Wolf of Wall Street were prestige projects, but Hill was called upon to, more or less, serve as a sidekick in a different genre. Now, Hill gives off the aura that he can have any role he wants. He will appear opposite Joaquin Phoenix in potential awards season darling He Won’t Get Far on Foot. Then he is set to play Olympic bombing suspect, Richard Jewell, in I am Richard Jewell.

As he stands in the top echelon of character actors, he continues to find challenges unlike anything he has done before. Recently, it was announced that Hill will star and executive produce the television series Maniac for Netflix. Patrick Somerville, a veteran of The Bridge and The Leftovers, wrote Maniac and True Detective helmer, Cary Fukanaga, will direct. The show is being pitched as a dark comedy that chronicles pharmaceutical trials gone awry. Hill will star opposite Emma Stone in what promises to be one of the most interesting and trippiest projects he’s signed onto in his career.

The evolution of Jonah Hill’s career offers a lesson to up and coming actors that might be feeling pigeonholed into a particular genre or type. Hill’s shift from funny sidekick to psychedelic leading man has only been possible because he took control of his career, enforcing the idea that to get his involvement, he needs to have some measure of creative input. First, this meant making choices that would show his range, but this has come to mean being set up as a creative force behind his projects.

In a world where media doesn’t just mean film and TV, but includes musical shorts, digital series, and promo videos, there are plenty of opportunities to show the world what you can do. The key for a young star coming from any form and any background in the Internet era is to develop a vision for the kind of work you want to be part of of and build your career to that point.

There’s no better model for that kind of growth than Jonah Hill. That’s why we always can’t wait to see what he does next.

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