For the last decade, celebrity photographer Tyler Shields has snapped his subjects with the access of an embedded photojournalist and the abandon of a Hollywood stuntman. In the pre-social media era of MySpace and flip-phones, Shields’s Southern charm and unfiltered eye attracted the likes of Lindsay Lohan and Mischa Barton, whom he captured wielding a blood-soaked knife and digging into raw meat, respectively.
With his front-row seat to mid-aughts hedonism (he was also pals with Brent Bolthouse, nightlife impresario behind clubs like Hyde and Area), Shields forged a symbiotic relationship with the guerilla-style gossip blogs of the day. “If Perez [Hilton] posted a photo by Annie Liebowitz, her lawyers would make him take it down. I went the opposite route; I said, here’s a photo of Lindsey Lohan, and I want everyone to see it,” Shields tells us.
Despite his thirsty reportage, his subjects were often the driving forces behind his boundary-pushing portraits, especially, as Shields reveals, in Lohan’s case. “When I met [Lindsay], I was summoned to her table at the Chateau [Marmont]. It was like meeting the Pope,” he says. “It was this hyper-ridiculous but amazing Godfather-esque thing. She said, ‘I thought you’d be older. Take my number.’ And then literally two days later we were shooting. That was how people met back then. Nowadays people just DM each other.”
Indeed, Shields’s style hasn’t always adapted smoothly to the Instagram age. Over the years, he’s has earned a reputation as a “bad boy photographer” – dropping increasingly provocative photo-shoots of everything from then-girlfriend Francesca Eastwood immolating a $100,000 Birkin bag, to more recent work defined by graphic depictions of social retribution. But Shield’s most explosive work by far came in 2017, when his Instagram post of Kathy Griffin holding the severed head of Donald Trump sparked a widespread backlash and, at least temporarily, derailed Griffin’s career.
But no matter the public relations crises his work has incited, Shields remains a fixture among the celebrity set – recently photographing multiple Willis sisters. “They’re just the sweetest, nicest family. They’re so giving,” he gushes.
Nor is he shying away from political work. In late February, he’ll release his YouTube Red documentary, which goes behind the scenes of his most recent photo series – an extension of his politically charged “Historical Fiction” series. “There was no lack of action. It will be entertaining at the least,” he says of the project. “But I think they got even more than what they bargained for. I’m excited for people to see it.”
Here, Shields takes us back to his pre-Hollywood roots – to his hometown of Jacksonville, Florida.
Cup of Joe: Honestly, where everyone goes in Jacksonville is Waffle House. Everyone goes there for late night, too.
Power Lunch: Woody’s barbeque is the best place. You want to get the beef sandwich.
Retail Therapy: Jacksonville is all about the malls. There’s a massive mall there, the Avenues mall. You’ve got the classic food court, the whole deal. As a kid, that’s what we would do. You’ve to get your Jordans.
Field Trip: There’s a native American fort that’s pretty untouched. One of the original forts is there in St. Augustine.
Date Night: Millhouse Steakhouse. I wouldn’t call it romantic. There’s a Morton’s, too, but listen. hen I was a kid, people would go on dates to Outback.
Don’t Miss: The Jacksonville Zoo. We have a crazy zoo.