▲His breakout starring role was his career's biggest success, but it also might have been part of what restricted Hill's dynamism in the industry.

▲In the film, Hill was part of a trio of spurned teens trying to lose their virginity at an end-of-year party. Years later, Hill spoke passionately to DeGeneres about the negative effects of the way boys are taught to look at sexuality as a social currency.

▲By 2010, Hill only fell deeper into the mould set for him by other people, and he starred alongside another actor typecasted for his appearance, Russell Brand.

▲For him, it was being that 14-year-old “overweight and unattractive kid who felt ugly to the world” and wanted desperately to fit in with skaters, but who didn't understand his own worth.

▲The magazine is dedicated to Hill's 14-year-old self.

▲Hill played exactly that curly-haired, goofy, overweight guy in comedy films like 'The 40-Year-Old Virgin' (2005) and 'Knocked Up' (2007).

▲“I came up in goofy comedies, you know, this kind of curly-haired, overweight kid, and everyone had their own opinion on what I should be, how they could speak to me, how they could treat me,” Hill told DeGeneres.

▲Hill used his nerdiness for nuance rather than comedy to portray his character Peter Brand, and it earned him an Oscar nomination.

▲In 2015, reports surfaced that Hill's friends were concerned with the actor's weight gain, though Hill was packing on pounds for his role in 'War Dogs.'

▲Hill asked his nutritionist to find out how he could still drink beer, because he said if he cuts it out he gets too thin, but when he drinks it he gets bigger.

▲In 2014, following a mix of great films ('The Wolf of Wall Street') and his usual comedies ('21 Jump Street'), Hill's name was well-known, but he was also accused of homophobia when he fired slurs at a paparazzo. He later apologized profusely on the radio, adding, "I am not good at being a famous person."

▲Speaking to ABC News about his drastic weight loss after 'Moneyball,' the actor explained that he didn't get surgery or take any pills, but that he saw a nutritionist and changed his eating habits.

▲Hill was doing voice-overs for films like 'Mastermind' and 'How To Train Your Dragon,' and starred in a much lesser known 2010 film called 'Cyrus,' which didn't get nearly enough public attention to help break Hill out of this unchanging path in Hollywood.

▲Hill recounted to Jimmy Fallon about asking his friend and '21 Jump Street' co-star Channing Tatum if he would get in better shape if he ate less and got a physical trainer, to which Tatum replied, “Yes, you dumb motherf****r, of course you will, it's the simplest thing in the entire world." That's what friends are for!

▲Come 2016-2017, Hill slimmed all the way down, filming the web series 'Maniac' alongside one of Hollywood's highest-paid actresses, Emma Stone.

▲Critics said the miniseries—a dark psychological drama about an experimental drug trial in which Hill plays a schizophrenic—featured the best acting that Hill has displayed in his career to date.

▲"Scumbro" is used to describe trendy people who favor priced-up streetwear brands like Supreme and Adidas, but who simultaneously love outdoor brands your elementary geography teacher wore. Hill, along with Pete Davidson and Justin Bieber, are all certified scumbro kings.

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From curly 'fro to buzz cut, and neon pink to bleach blond, Jonah Hill has rocked them all.

▲Hill's good friend Channing Tatum flew in to award him a GQ's Man of the Year award for being “as sharp a filmmaker as [he is] a star in front of the camera,” which is surely the first of many accolades to come.

▲At some point Hill changed from the butt of the joke to the darling of the Internet, growing out of the character cool kids make fun of and into the character that cool kids want to be.

▲He plays a gay alcoholic in a darkly humorous drama alongside Joaquin Phoenix, and his tenderness and maturity in the film show a soft underbelly to Hill's persona.

▲When people stopped paying attention to his weight, they started to notice his clothes. The second annual Jonah Hill Day was held in Brooklyn, New York, and functioned largely as a way to pay tribute to Hill's fashion sense. “People like how I dress, which I think is very flattering,” Hill told Jimmy Kimmel.

▲"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," reads the manifesto. "And it's only in the last four years writing and directing my movie, 'Mid90s,' that I've started to understand how much that hurt and got into my head."

▲Hill spoke to Ellen DeGeneres in 2018 about how everyone has a snapshot of themselves that they’re ashamed of and that they try to hide through fame, success, good looks, or anything else, and how you always carry that snapshot with you.

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He said it best: "I'm under construction like we all are."

▲Hill told DeGeneres, "It took a long time—honestly until right now" for him to come out as the person, artist, and mind that reflects who he really is, instead of something he's not. He said he's finally gotten to a point where he himself can determine how he feels, how he'd like to be spoken to, and how he wants to speak to the world.

▲Hill described the film as a story about learning to love yourself and finding a community of people who accept you.

▲Hill guest-edited a magazine, published by film company A-24, that focuses on self-love in an effort to help anyone else struggling with self-image.

▲It's a stretch, but if the point is that Jonah Hill is equally as good looking as Bradley Cooper, then point made!

▲In 2019, Hill had a successful year. He voiced character's in several films, starred in 'The Beach Bum,' executive produced 'Good Boys,' and got engaged to his girlfriend, Gianna Santos. But in October 2020, their split was announced.

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In September 2021, Hill went Instagram official with his new love, Sarah Brady. She was also his date to the premiere of 'Don't Look Up' (2021). But by August 2022, the pair seemed to have called things off.

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The media has long held a keen interest in Jonah Hill’s fluctuating weight and, with that, the roles he’s taken on in the world of film and art. From his breakout role in ‘Superbad,’ to helping create a profound magazine on self-love, the actor, director, writer, and producer has never stopped evolving under the burning glare of the public, and he says he’s just starting to reclaim his identity.

Check out this gallery to see how Jonah Hill defied expectations and became the talented actor, first-time director, and unexpected style icon he is today.