Perez Hilton: The Original King of the Trolls

· Updated on October 30, 2018

Before I left this earth, I needed to ask Perez Hilton what he thought of Donald Trump.

The gossip blogger was arguably the Internet’s first supervillain, a widely loathed figure who trolled his way into being a household name during the height of the media’s “mean girl” era. News coverage from the mid-2000s charitably describes Hilton as “divisive.” He is perhaps the only person to ever be compared to both Hedda Hopper and Ann Coulter. Former Desperate Housewives actor Jesse Metcalfe reportedly confessed to Hilton at a party that he’d fantasized about killing him. Bodyguards for acted on that animus in a 2009 altercation, giving Hilton a nasty black eye.

Does Hilton see any parallels between himself and the occupant of the Oval Office? Or even figures like Milo Yiannopoulos, the alt-right enfant terrible who harassed Ghostbusters actress Leslie Jones on Twitter? Last year, Yiannopoulos urged his followers to tweet racist photos at Jones, comparing her to a gorilla. Breitbart, the website which once employed Yiannopoulos, claimed that he is “just the modern-day version of Hilton.”

Hilton doesn’t see a connection.

“The difference is I believed everything I was saying,” Hilton tells me over the phone. “It might’ve been exaggerated, but I truly believed what I was saying. I don’t believe half of the shit that comes out of [Yiannopoulos’] mouth. I think he says what he says just to get attention.”

The 39-year-old is more measured in his take on Trump, who he believes capitalized on America’s obsession with the rich and famous: “His voice was the loudest, and celebrity helped him in a big way.”

“It’s that [Trump] said things that nobody ever said before, and quite frankly, I don’t think there will be anybody else operating like he has,” Hilton argues. “It’s not presidential. You don’t say the things that he does. You don’t tweet the things that he does. People thought he was gonna change when he became president, but the dude’s in his 70s. He is who he is. He’s never going to change.”

Hilton, though, says he is not the man that he used to be.

The proprietor of what once proudly described itself as “Hollywood’s most hated website” has been on a redemption tour since 2010, when he resolved to become a kindler, gentler version of the controversial firebrand who peppered Lindsay Lohan’s nose with Microsoft Paint cocaine dots.

Following the suicide of Rutgers student Tyler Clementi, the openly gay blogger (neé Mario Lavandeira) filmed a video for Dan Savage’s “It Gets Better” campaign, urging LGBTQ youth to hang on. The message was a personal one for Hilton: After failing to make his big break as an actor led to an unfulfilling job working as a magazine editor, Hilton wrote in a 2007 op-ed for The Daily Mail claiming that he considered taking his own life.

The reaction to his testimonial, Hilton says, was “overwhelmingly negative.”

“People were saying, ‘How dare you make an It Gets Better video when you’re a part of the problem? You’re a hypocrite, you’re a bully,’” Hilton says. “So I did a lot of soul searching and reflection.”

Even though the man behind it is different, Hilton claims that his gossip website hasn’t changed much since the days when Britney Spears teetered on the brink of collapse and Amy Winehouse crooned that she would never go to rehab. He points to someone like Sharon Osbourne who has remained unapologetically herself:“She’s so opinionated, but I wouldn’t say she’s a hated individual.”

During our hour-long call, Hilton was surprisingly earnest for someone who made his career based on an invented persona. Just as often as he appeared to contradict himself, I was taken aback by how forthright Hilton was. He manages to be many things at once.

But that doesn’t make Hilton’s claim that everything is “business as usual” (my scare quotes, not his) even remotely true.

Back in 2007, the blogger would make up derogatory names for celebrities he didn’t like, drawing semen on their faces to better express his distaste. Jennifer Aniston, fresh off a divorce from Brad Pitt, became known as “Maniston.” Ashlee Simpson, younger sister of singer Jessica Simpson, was dubbed “Asslee.” Kirsten Dunst, then in rehab for alcohol addiction, earned the moniker of “Kiki Drunkst.” To add insult to injury, his posts about the Spider-Man actress frequently pointed out her “snaggletooth.”

Hilton’s celebrity coverage was juvenile and cruel, but his ribald humor could be funny. (There’s a reason his site got millions of hits a day at its peak.) When compared to the cut-and-paste PR of People magazine, Elaine Lui of Lainey Gossip tells me that it seemed “fresh, radical, and ballsy.”

“At the time, we were questioning the legitimacy of outlets that were known to be the main sources for entertainment news,” says Lui, who was likewise at the vanguard of the first generation of gossip bloggers. “They were always reporting the safe, sanctioned, sanitized celebrity stories. A lot of people felt that these people weren’t as squeaky clean as we thought they were.”

“Perez and the rest of us were part of a new wave of questioning celebrity behavior and questioning their perfection,” she adds. “Hilton just did it with those pictures but underlying those pictures was a subtext: These people are full of shit.”

Hilton says his approach was to see the famous as messy and human: “Before blogs like mine, celebrities were royals. I just talk about them as if they were normal people.”

Those flaws have largely been airbrushed from the of 2017; its tone is not venomous but fawning, studiously beatific. The blogger claims that his mantra these days is: “What Would Oprah Do?” A series of recent posts on Taylor Swift’s “groping trial,” in which she accused a radio personality of grabbing her butt during a red carpet appearance, applauded the singer for sticking up for victims of sexual assault following a favorable verdict in the case. “What victory!!!” he proclaims.

During a write-up of Miley Cyrus’ interview in the September issue of Cosmopolitan, Hilton credited a revealing Versace look from the 2015 VMAs as “iconic.”

It’s a pretty jarring shift from 2008, when he referred to Cyrus’ infamous Vanity Fair photo shoot, in which the former Disney star was photographed in a bedsheet, as “slutty.” Cyrus was 15 at the time. Two years later he would post photos which appeared to show the singer getting out of a cab without underwear, leading to accusations that Hilton was “distributing child pornography.” His defense was that Cyrus was actually wearing undergarments. Hilton said at the time that he merely hoped to point out the “very unladylike fashion” with which she was conducting herself.

What a difference a decade makes: The blogger who once made celebrities’ lives a living hell is now sucking up to them. He even leaves cheerfully thirsty comments on their Instagram posts.

But if Hilton’s blog has evolved, he may not have had a choice. His traffic is a fraction of what it once wascurrently ranked by Alexa as the 5,965th most popular website in the world. The knowing cattiness of gossip sites D-Listed and The Awful Truth largely went out of fashion following the rise of what The Awl’s Choire Sicha called “The New Niceness,” epitomized by the feel-good clickbait of BuzzFeed and Upworthy. These websites drew readers in with the promise of instantly shareable inspiration, not the destruction of the powerful.

“If someone came around today and started doing what Perez Hilton did then, people would be horrified,” says Richard Lawson, a former Gawker writer who has since become a film critic at Vanity Fair. “Many people were not horrified 10 years ago.”

Lawson credits platforms like Twitter and Facebook for bringing marginalized voices to the table who served to challenge the more unsavory aspects of Hilton’s work, which Lawson says was often used to “denigrate women and contribute to the downfall of these sad female celebrities.” When the blogger posted leaked nudes of actress Jennifer Lawrence in 2014, Hilton apologized and removed them following rabid public backlash. He said in a YouTube video the decision to run them was made in haste.

“Sometimes when news is breaking you’ve got to make a decision and it’s the wrong one,” Hilton says now. “But I’ve learned from that one.”

Here, though, Lawson offers a disclaimer: It’s easy to point the finger at Hilton, but so many websites were doing exactly what he did before social media made them accountable. Hilton was just better at being bad.

“It’s a similar narrative to why people watch the Real Housewives,” says Lawson. “We want to watch shows about men doing things and women bickering. On the record, I would like to say that I was part of that culture as well. I wasn’t out there saying that this is bad for women. I wasn’t. I was young and I was following the trend.”

Hilton says that changing his stripes had to do with shifting away from his trademark persona (but curiously enough, he asked me to call him “Perez” during our phone conversation). That charactera Sancho Panza-like figure whose name was derived from tabloid queen Paris Hiltonhe compared to a “court jester” or “lovable fool.” Lui, who claims that she found Hilton shy and withdrawn in person, adds that Hilton “went out of his way to live up to being obnoxious, provocative, and flamboyant.” It was all part of selling a brand.

According to Hilton, the person readers encounter on his site today is closer to who he actually is: “a boring dad who works too hard.” Years after he decided to forge a new path, the father of two is concerned about the direction America is headed. His recent posts on the violence in Charlottesville appear to reflect that shift in his priorities.

When Hilton’s four-year-old son, Mario Jr., recently turned on the TV screen at the gym, he pointed to the screen and exclaimed, “That’s Donald Trump!” “How do you explain Trump to someone so young?” I asked Hilton. He says that he didn’t. Prior to that moment, Hilton wasn’t even aware that his son — who was conceived through a surrogate — knew who the president was. But it turned out that Mario Jr. had been learning about Trump in school.

“I wanted him to live in a nice, safe protective bubble with no awareness of the awful person in the White House,” Hilton says.

Say what you will about Hilton, but he’s nothing if not a survivor, one of the few remaining holdouts of a bygone era of the Internet. Pink Is the New Blog, a site which offered a nicer counterpart to Hilton, was bought by SpinMedia in 2011. Creator Trent Vanegas tells me over the phone that by the time he moved on four years later, it was time for a change. Spin would respond by changing the site’s name to “Socialite Life” following Vanegas’ departure, effectively gutting the once popular blog.

Bruce Bibby, the retired gossip columnist once known as Ted Casablanca, now runs an art gallery in Palm Springs. (Bibby was unavailable for comment before publication time.)

Michael K, the creator of D-Listed, argues that the reason that the old guard of gossip media largely died off isn’t just due to changing social mores. If entertainment blogs replaced tabloids because they could beat print media to the punch by posting multiple times a day, social media could do what bloggers couldn’t: They could post stories instantly.

“We always say that Twitter killed the blogs,” he says. “On Twitter, you can get snarky commentary faster, quicker, and shorter. If a story breaks, we can’t get it out in milliseconds.”

The new Hilton, somewhat improbably, is just as busy as the old one was. He still commands over 2 million followers on Facebook. After making an extremely brief cameo in Absolutely Fabulous: The Movie last year, he’s finally fulfilling his dreams of being a film star. In 2017, Hilton is slated to appear in four movies and a reality show. The celebrity edition ofAmerica’s Worst Cooks, co-starring Erik Estrada, Carmen Electra, and Carson Kressley, will air on the Food Network on Aug. 23. Hilton claims that the experience was like a “paid vacation.”

Not everything is paradise, though. Shortly after we spoke, Hilton posted a video to YouTube in which he sobs after being fired from a “dream job,” declining to specify the gig that prompted the breakdown.

But in the second decade of his career, the reformed troll (he claims he still likes to dabble here and there) looks at someone like Joan Rivers as a model for what he wants his career to become. The legendary comedienne, he says, was someone who wouldn’t turn down any opportunity thrown her way. Rivers kept working all the way up until her 2014 death.

“If someone’s willing to pay me to do something, I’ll do it,” he claims.This was the last question I had written down for myself to ask. But as the interview draws to a close, I realize that I have one more: Now that Hilton claims to have turned over a new leaf, does he ever feel guilty about what happened to women he terrorized? Spears was placed under the conservatorship of her parents following a mental health breakdown — one in which she famously attacked a photographer’s vehicle with an umbrella. Lohan was frequently in and out of rehab, clearly trying so hard to get it together but never seeming quite able to.

Hilton certainly didn’t do anything to avert a disaster that always felt looming just over the horizon; he often egged it on. Following Heath Ledger’s death in January 2008, Hilton put out t-shirts asking why it wasn’t Britney instead.

The answer: Yes and no. Hilton offers the proverbial “short skirt” argument in his defense.

“Back then, I didn’t feel any guilt,” he says. “Back then I loved it, and back then, I would say they loved it, too. I would say there’s a reason so many of them repeatedly weren’t wearing panties. They wanted to be photographed without wearing panties and get that attention. There was this new world of the Internet with people talking and commenting and that was like a drug to them.”

“Some people never kick it,” Hilton adds.

I ask him if he has kicked it. Hilton responds that he was “never a drug addict in that sense,” but I don’t know if that’s the truth. I don’t think he knows either.

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