Jonah Hill Day: how the nerdy comedy star became an avatar for the modern-day glo-up

A new annual celebration of the actor indicates a cultural shift that has made the aspirational attainable for a generation of young men, says Ben Allen

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On a sticky-hot day in June of this year, dozens of New Yorkers – journalists, fashion bros and their disciples – gathered at a small outpost in Brooklyn for Jonah Hill Day 2018, the second annual day-long party and unofficial celebration of the Wolf of Wall Street star.

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The event had been hastily dreamt up the previous year, and sold as a “bad excuse for a good day party” on the flyers posted to social media.

At around 2:45pm (the event was set to begin at 2pm) – the party’s hosts, Lawrence Schlossman and James Harris of the fashion podcast Failing Upwards, who have been credited with shaping Jonah Hill’s unlikely journey from schlubby funny man to street style icon – were pre-loading at a friend’s apartment. Suddenly, their group Whatsapp started to blow up.

“You guys aren’t going to F***ING BELIEVE THIS,” their intern Chuck wrote. The party had yet to really take off, and the majority of people in the bar, who were fixated on the World Cup match between Uruguay and Portugal, hadn’t noticed a stylish man slink in at the back. Against all odds, Jonah Hill had arrived. 

Jonah Hill: Fashion Icon

If you’re an active Twitter user, you’ll have likely noticed the prominence, in recent years, of paparazzi shots of Jonah Hill circulating the site. For this, you can thank Lawrence Schlossman.

The Failing Upwards host and former editor-in-chief of Four Pins, a fashion-centric Complex sister site, began sharing snaps of the star from the now-defunct publication’s social media accounts in 2016, when he noticed that Hill’s style had improved dramatically since the Superbad days.

“There was this period of time where he kind of stepped away from the public eye and then re-emerged, post his two Oscar nominations [for Moneyball and The Wolf of Wall Street], at some point in 2016,” Schlossman says. “He moved to New York [from LA] and he was getting paparazzi-d, and he looked awesome – he was wearing really cool brands, mixing high fashion with streetwear.”

Thanks to Four Pins’ considerable reach (Schlossman still controls the Twitter account despite the site going under, and it currently has over 600k followers), Hill’s looks became a recurring talking point on fashion Twitter, and before long, people began to take him seriously as a style icon. An Instagram account dedicated to his ever-expanding wardrobe was created, and foremost streetwear fashion publications HighSnobiety and Hypebeast began to drop his name. Soon, even the big boys caught on.

“He was packaged in this way of like ‘holy shit, this dude is awesome and fly and not only is he the hilarious kid that you remember and now this critically acclaimed actor, but also this cool ass f***ing young dude in New York living life on his own terms,” Schlossman says.

Hill’s rise was all the more significant as it broke the mould of who and what is considered cool in the fashion world.  

“Jonah isn’t the kind of person that men’s style fans would normally latch on to,” says Schlossman, who also serves as the brand director for high-fashion re-sell site Grailed. “In 2016, it was all about rappers like A$AP Rocky, and Kanye West has always been the centre of all this stuff, everything seemingly orbits around him. And people really care about what NBA players are wearing and all that. Jonah doesn’t look like those guys, so it catches people off guard.”

And, it has to be said, few people could have anticipated that the kid from Superbad would be defining street style in 2018.

Highsnobiety’s editorial director Jian DeLeon, who was in attendance at Jonah Hill Day 2018, says that Hill’s authenticity is particularly refreshing in a world where celebrities are being styled to death.

“He represents how a lot of real dudes get dressed,” DeLeon says. “He gravitates towards things that make him look and feel nice, and wears them in a non-affected way. It helps that a lot of the brands he likes happen to fall into the realms of skate brands and streetwear brands.

Hill can often be seen sporting Palace, a London skate-wear brand, and Lotties, according to DeLeon, a “a seminal independent skate shop in LA”.

“There’s something about Jonah that was more organic and natural,” Schlossman adds.

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Hbd, Fit Deity 🎂 #OlajuwonYear

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For Hill, this new and unexpected attention took some getting used to. He knew the first Jonah Hill Day was happening in 2017, but had originally misinterpreted it as a cruel gag.

“I was too shy, I didn’t really get it,” he said in an interview with Jimmy Kimmel earlier this year, “like, is this a bit – are they making fun of me?”

Many of the uninitiated who see these pictures of Jonah cropping up on social media have the same reaction – myself included. The Four Pins account regularly captions its pictures “Jonah Hill Fit Watch” – referring to his outfits, rather than his fluctuating weight – which has caused further confusion. But Schlossman assures me that there is no irony involved.

“We think what he represents is like this really cool aspirational but also attainable avatar for young men who have grown up with him, and are trying to accomplish a lot of the same things that he has kind of done, which is commercial and critical success combined, this idea of the quote unquote glo-up.”

This has as much to do with the actor’s career trajectory as his penchant for cool threads.

Eleven years after making his debut as a Seth Rogen stand-in in Judd Apatow films, he has successfully subverted expectations to become one of his generation’s leading dramatic actors – acknowledged by Oscar nominations in 2012 and 2014 – and later this year he will release his directorial debut, Mid90s. And no, it’s not a comedy.

Schlossman continues: “I think that trajectory he has been on is something that is easy for young men to galvanise around, and I think that’s why you’ve seen the perception around him change dramatically in the past year because I think he does represent a lot of things that young men, whether they’re fashion fans or film fans, they look at him and they see a path for themselves.”

Jonah Hill Day 2018

Scrambling to sober up and arrive at their own party before the unexpected guest of honour left the vicinity, Schlossman and Harris hot-tailed it to Brooklyn.

Hill, having been reliably informed that the party would commence shortly, slinked off around the corner to grab some lunch and returned an hour later to find the place considerably more turnt up.

Jonah Hill and Lawrence Schlossman at Jonah Hill Day 2018
Jonah Hill and Lawrence Schlossman at Jonah Hill Day 2018 (photo courtesy of Dylan)

Before long, he was stood next to a cut-out of himself wearing a tie-dyed Grateful Dead t-shirt, white slacks, white loafers and a white cap, chatting jovially with fans and taking pictures. The crowd, made up of followers of the Failing Upwards podcast – where Schlossman and Harris frequently reference and “gas up” Hill’s style – and friends from various fashion outlets and publications such as HighSnobiety, Complex and Fashionista, swarmed tentatively around him.

“It was a quintessential New York moment,” Schlossman tells me. They had supported Jonah Hill through various outlets, and now Jonah Hill had arrived, in turn, to support the homies.”

It also cemented Hill’s relationship with a pocket of his fans, who flocked in to celebrate the star, with little to no expectation that he would actually make an appearance. 

“At one point I looked into the crowd and saw the Jonah cutout getting hoisted into the air and people were worshipping it like a statue of a god,” Mike, a 24-year-old finance worker who attended the event, says.

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Photo courtesy of Mike McClatchey

Mike turned out for Jonah Hill Day with his friend Dylan after hearing about it on Failing Upwards, having missed out on the 2017 inauguration. He and his friend speak about it with great reverence, echoing Schlossman’s sentiment that something special had occurred.

“There were really no lines between who was a celebrity and who wasn’t, everyone was talking to each other and hanging out,” Mike says. “Everyone was there just to have a good time. You could easily identify who was there for JHD based on the outfits, who came with their friends and didn’t fully understand the concept of JHD, and a few people that were probably Kinfolk regulars who got caught up in the mayhem.”

“Jonah is absolutely a style icon in my eyes,” he adds.

JohnVan Lieshout, a food and beverage manager based in Manhattan, helped out with planning the party, and was equal parts delighted and flabbergasted to be see the man himself turn up on the day.

“I’d say Jonah Hill is more of a lifestyle icon than a style icon for me,” John says. “I love how he blends high/low with wacko maria shirts and Patagonia baggies.” He adds that the party was “like a big f***boy family reunion in the best way possible.”

And the actor seemed to have some strong feelings about the event himself. Delivering a speech in front of his cut-out, he beamed a self-conscious mixture of amusement and flattery.

“This is the most surreal, epic, flattering and enjoyable thing,” he said.

Hill has been candid about his struggles with the pressures of fame in the past, telling New York Magazine in a profile interview earlier this month: “You can’t live in a world where you’re wondering what people think of you. It will just drive you crazy.”

And it’s easy – and probably wise – to be cynical about the effect the internet and social media have had upon celebrity culture. But, every now and again, it has the power to surprise you.

Somewhere along the way, Hill recognised that the internet was showing him love, and chose to embrace it. A couple of weeks after the fact, he expanded upon this sentiment on Jimmy Kimmel Live.

“I’m kind of in a new wave,” he said of his decision to crash Jonah Hill Day 2018. “So I was like, these guys are showing me love – I think it’s about how I dress. People like how I dress, which I think is very flattering.”

“This year, I was like, you know what, I need to get over my social anxiety – and I went in there, and I freaked it.”

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If his glo-up wasn’t complete before, it is now.