At the end of April, numerous media outlets reported that Paris Hilton was in a relationship, the happiest one of her life.
If this sounds familiar, it should; the coverage of Hilton’s love life is now entering its third decade, and though the interest has waned from where it once was in 2004, the news — and that I even cared about it — made me self-reflect: Why do I still care about who the heiress is canoodling with?
It’s likely because in the early aughts, I really, really wanted to be one of those boyfriends, because being Paris Hilton’s boyfriend meant more than just dating a ditzy blonde.
In the 2000s, there was only one person whose fame outstripped the public’s ability to figure out just exactly why they cared about her. Sure, there were plenty of other heiresses sunbathing topless in St. Barts and doing cocaine on boats, but we didn’t know their names, buy their homemade sex tapes for $50 or watch their hijinks on network television. Though the aughts were littered with It Girls like Chloë Sevigny, Lindsay Lohan and the Olsen twins, what set Hilton apart, in a pre-Kardashian world, was that she appeared out of thin air. She had no recognizable talents or achievements, and instead of insisting that she did, she leaned into her insouciance, which made her seem dumb, and in turn, made the American public (myself very much included) follow her every move.
For this reason, I’ve long held one singular belief: Paris Hilton is a genius.
Call her an evil genius, if you please, but a genius all the same. Just ask Simon Rex, who dated Hilton off and on for a few years. “People think Paris is a ditzy blonde, and I don’t want to blow it for her, but she plays it really well,” he told Mediaite in 2009. “She knows exactly what she’s doing. She said something interesting to me once. She said, ‘I just tell everyone what they want to hear, and I do what I want to do.’”
Rex exists among the canon of Hilton paramours, a large, highly visible manifestation of her genius, a performance artist’s study in boyfriend curation. Individually, these men — largely white, mostly rich (though not as rich as her) — mean very little to us. They look like a string of (mostly) fun flings. But taken holistically, it’s clear that Hilton engineered a museum-quality exhibit of lovers to suit both her tastes in the moment, and for us to bask in for posterity: dirtbags, smut peddlers, Greek shipping heirs, pop punks and conventional hunks.
Hilton claims to have invented the selfie and dancing on tables, but she certainly didn’t invent having a list of Hollywood exes longer than the unabridged version of The Stand. She did, however, revolutionize the boyfriend as an accessory — a way to move seamlessly between worlds — using different archetypal men for dual purposes: to have fun and to remain in the zeitgeist. And the relationships were mutually beneficial. It’s hard to overstate how easily just dating Paris Hilton in the early aughts could create cultural cache out of thin air. To date Hilton meant daily coverage — your sweaty red mug in an Ed Hardy T-shirt — in the New York Post or on Perez Hilton.
Hilton’s romantic relationships — and, in fact, her rollercoaster relationships with friends and enemies — were covered breathlessly, set to a baneful chorus of WHY IS THIS NEWS?, sung by a choir of masochists who couldn’t turn away. Because Americans define themselves by their work, Hilton was initially reviled because she didn’t do anything for a living beyond make a sex tape with Shannen Doherty’s ex and be the heir to the Hilton Hotel fortune. She didn’t engender any sympathy for herself in this way by insinuating that non-billionaires like her forever feud-mate Lohan were poor and dating a string of rich kids who also didn’t do anything besides, seemingly, use the doors on clubs and limousines and have parents who owned fleets of ships in the Mediterranean.
Not like it really mattered, though. Dating Paris Hilton wasn’t like being in a relationship, it was entering into a sponsored-content partnership. I’m not too proud to admit that I wanted to be one of these boyfriends: dumb and drunk and in love, sleeping all day, yelling outside a $500,000 Mercedes Benz SLR McLaren all night. Not to discount the actual, genuine mutual affection between Hilton and her array of himbos, but from the outside, the attractiveness of being the other person in this partnership was the lifestyle. Sex with a svelte blonde is cool, but have you tried receiving regular newspaper coverage because your girlfriend is rich?
Hilton attempted acting, a singing and DJing career and all the other types of occupations people in the tabloids generally have before their love lives are picked apart. But nothing stuck, except, well, her dating life.
As such, here is a cultural history of that life, broken down by boyfriend archetype…
The Dirtbags
Edward Furlong — who became famous for playing John Connor in Terminator 2, and starred in American History X, Detroit Rock City and John Waters’ Pecker — dated Hilton in 2000. This news item from September of that year, when the two had been seeing each other for about a month, will paint a picture of both what it means to be a dirtbag, and what dating Hilton looked like back then. Hilton was just 19 and not yet known as the partier she would become. Seeing the two side-by-side was an incongruous juxtaposition: Hilton clad in designer heels, hair immaculately done, embraced by Furlong, perpetually smoking a cig, sporting baggy jeans, a greasy mane and watery, wandering eyes.
One night, Furlong and Hilton were partying at one of those mononymously named New York nightclubs when Furlong mistakenly entered the ladies’ room, ordered a drink and then immediately barfed all over the bar. Hilton’s spin, incredibly, was that “he did not throw up,” and the same story mentions an earlier incident two weeks earlier, when Natasha Lyonne (Furlong’s ex) allegedly called Hilton a “fucking slut.”
This was one of the earliest instances of casual misogyny lobbied against Hilton, with the author of an ensuing ABC News piece calling to question her refutation of claims of partying topless with Furlong in Vegas by stating, “Those who recently saw the skanky spread of young Paris in Vanity Fair might beg to differ.” It was also the beginning of another trend in the heiress’s dating life — the ubiquity of a nightclub spat between Hilton and another famous woman.
Four years later, Hilton dipped back into the dirtbag waters when she was snapped stepping out with Limp Bizkit lead singer Fred Durst, the ur-dirtbag for the late-1990s and early aughts. The juxtaposition between the two, as it was for Furlong, was stunning as they left L.A. Japanese restaurant Koi in August 2004, Hilton looking demure in a spaghetti-strap, drop-waist dress and gold pumps, and Durst in his ubiquitous backwards cap, a Smiths T-shirt and baggy cargo pants.
Hilton had many types, but the dirtbag both hardened her image and made her look chic by association. Though Hilton generally aged out of dating straight-up dirtbags, many, many of her exes contain dirtbag tendencies, as you’ll see below.
The Smut Peddlers
Though Hilton dated Rick Salomon in 2001, their relationship made true headlines in 2003, when their sex tape — later released on DVD as One Night in Paris — was leaked. The leak made her a household name, created an intense backlash to that new fame and eventually positioned her as, if not a victim, a victim of circumstance, creating some sympathy for her in the process. Hilton insisted that Salomon released the sex tape against her wishes (even once claiming that she didn’t remember a tape being made), but the most cynical critics noted that the leak predated the debut of her reality show, The Simple Life, by mere weeks.
Perhaps this was part of a larger marketing campaign by the brand Paris Hilton, and the person Paris Hilton would have to take a minor hit in order to become a bona fide star, which she became when The Simple Life premiere drew 13 million viewers. Hilton sued a Panama-based internet company for distribution of the tape, and Salomon sued Hilton and her family for slander after they released a statement about the tape and Salomon that he says they never retracted.
Hilton engaged in an all-out war with Shannen Doherty, Salomon’s ex, around the same time. Doherty allegedly punched Hilton in the face and egged her car, and Hilton fought back with… some threatening voicemails. What the relationship with Salomon did was plant the seeds for a conversation the culture wasn’t quite ready to have yet — and wouldn’t have until even after Hilton’s erstwhile pal Kim Kardashian starred in a celeb sex tape of her own in 2007. Hilton coverage for the next decade or so contained an undercurrent (and sometimes overt) tone of condemnation for whatever it was Hilton did wrong here, which is, plainly, having sex with her boyfriend on camera.
Though Salomon became a pornographer after their relationship ended, that didn’t scare Hilton away from crossing paths with one of the more nefarious members of the adult industry at the time: Girls Gone Wild creator Joe Francis, who was later convicted for false imprisonment, assault and a bevy of financial crimes. The two dated, briefly, in 2003 — though Hilton has since denied any romantic association, and Francis didn’t respond to an interview request for this story — but the relationship is most notable for Hilton’s role in helping catch the man who committed a home invasion and extortion plot on Francis.
Hilton cracked the case, literally at the club. She was doing shots one night behind a bar when a man started bragging about the extortion tape another man made of Francis. Later interviewed by investigators, her recounting of this story led to an arrest. Overall, I’m not sure what the relationship proves other than getting drunk at the club is technically a job after all.
The Greek Shipping Heirs
One way to date Hilton in the early aughts was to be an heir to a petroleum-related fortune. While this may seem like an ultra-specific category, Hilton actually dated two Greek shipping heirs, consecutively. Famously, Hilton cozied up to Stavros Niarchos, Mary-Kate Olsen’s ex and grandson of a billionaire shipping tycoon, but not before dating (and planning to marry) another one who shared her given first name. The important thing here is generational wealth: What does an heiress have to talk about with an actor or a musician worth a piddling eight figures?
Paris Latsis became Hilton’s second fiancé in May 2005, after the pair dated for eight months and the eventual billionaire — he inherited $7.4 billion in 2003 — allegedly gave Hilton the choice of 15 different engagement rings. The Paris x Paris collab was set in motion nearly a decade earlier, when as teenagers, Hilton and Latsis met at a club in Monaco (super-relatable).
Their partnership was, to this point, the most conventional and real-seeming of Hilton’s life. Latsis seemed genuinely sad after the breakup— “I love Paris very much,” he remarked — and his statements to the press in the wake of their relationship indicated a new depth in Hilton. Up until that point, she was portrayed as a rich, beautiful, blithely ignorant layabout, born for bottle service and not much else. That Latsis considered his relationship with her “the best experience of his life” is revealing. Perhaps he was taking the high road, but it should be noted that Latsis never had a public spat with, nor said a bad word on the record about, his ex.
Mere days after announcing her split from Latsis — on the grounds that she was too young to get married and didn’t want to “make a mistake with the whole world watching” — Hilton hooked up with Niarchos. The relationship is notable in that it ignited perhaps the most infamous (and confusing) feud of the aughts, one that apparently continues to this day.
After one-time Hilton pal Lohan was spotted out clubbing with Niarchos in 2006 — apparently during one of the “off” moments of their on-and-off relationship — Hilton, as always followed by a phalanx of paparazzi regardless of what she was doing, responded (sort of). Her friend, dirtbag oil heir Brandon Davis, called Lohan a “firecrotch” as Hilton smirked beside him. This would lead to the two spending the next few months insulting each other (Hilton insinuated that Lohan was poor; Lohan mocked the Hilton sex tape), insisting they were friends and then insulting each other again either through the press or outside clubs. In 2018, Hilton called Lohan a “pathological liar,” and just last year, “lame and embarrassing,” a statement that would have had legs in 2007, but quickly faded into the blank hellscape of cultural content.
Ultimately, this archetypal boyfriend established the most holistic representation of Hilton. With Latsis, she largely negated the One Night in Paris version of herself, to become a caring, loving girlfriend who wasn’t quite ready to settle down. But in an instant, she torched that image — Hilton as a housewife did little to move the needle for her brand — with Niarchos. It’s almost as if Niarchos was the v2.0 of a Greek Shipping Heir experiment, the relationship designed in a lab. Latsis was means-tested and determined to be too boring and conventional. Niarchos was like Latsis on paper, but ultimately, much more volatile — and thus, theoretically able to keep her name in the paper. He trashed hotel rooms, tossed drinks, crashed Hilton’s Bentley and did other things we could gawk at.
Most importantly, though, their coupling thrust Hilton into another level of fame.
The Pop Punks
There is no way that Hilton could have dated, say, punk-rock party boys like Hot Rod Todd from Le Shok (once voted one of the scariest people in Orange County) or even a member of Rancid, no matter if Tim Armstrong used to love wearing a fedora. But at various points in her dating life, Hilton did the thing that popular girls did in high school from time-to-time, in deigning to date, lol, a (pop) punk guy!
In 2003, pre-mega-fame, Hilton swerved her Bentley onto Frosted Tips Avenue, dating the frontman of Ontario’s most SoCal band, Sum 41’s Deryck Whibley. Hilton seemingly stuck to Whibley for a few months because he kept giving the finger to paparazzi, maybe the most punk thing she’d ever witnessed. Though Sum 41 — and really all pop punk in the early aughts — was merely bouncy alterna-rock re-packaged for the TRL set, for someone who once attended the Professional Children’s School (current tuition approaching $50,000 annually), dating Whibley was like a normal person dating GG Allin.
Three years later, Hilton started partying with Blink-182 drummer Travis Barker, which made his ex-wife Shanna Moakler very angry. “I hope you guys both fucking die,” Moakler texted Barker around that time. This was squarely in the zone for Hilton in 2006 when she was dating other famous women’s exes — she loved to be photographed on their arm or making out in a limo to draw the ex’s ire. Hilton’s response was generally an eye roll and another shot of Grey Goose, which then made her enemies even more upset.
In the end, Barker said he dumped her because their “sexual chemistry was never good.” Then — and you’ll never believe this — he made out with Lohan. So petty.
After another pop-punk sabbatical, Hilton dated Good Charlotte singer Benji Madden for nine months in 2008. Apparently head over heels for her, he told People magazine, “I’m very open about how in love I am — Paris and I are very happy,” just a month before they ended it. Almost immediately after they broke up, Hilton was spotted out with Niarchos.
The Conventional Hunks
Through all of the above, Hilton regularly took some time away from guys who chain-smoked Parliaments, or whose grandparents jockeyed with Aristotle Onassis for shipping routes or who sang snottily over octave chords to date boring looking — but ultimately attractive, by [Joker voice] society’s standards — dudes.
After breaking it off with Furlong, Hilton hooked up with — and was once engaged to — a fashion model named Jason Shaw, a sentient crisp, untucked button-down. Because all men in Hollywood are around five feet tall with pumpkinheads, the 6-foot-2 Shaw stands out among her aughts exes, towering over Hilton, who is generally listed at 5-foot-8. Hilton broke it off with Shaw because [insert quote from PR person], but they briefly dated again in 2010.
Hilton’s most conventional looking (and famous) of her “long-term” exes is Nick Carter, the platinum blond, mop-topped former Backstreet Boy, whom she dated in 2004. The relationship ended badly, with an anonymous source accusing Carter of assaulting Hilton after a photo emerged of her with a fat lip and bruises on her arms. The point was argued through the New York Post and People, with Carter’s camp insisting that Hilton’s injuries were the result of an S&M photo shoot with David LaChapelle, which Hilton’s rep denied. In his 2013 memoir, Carter wrote, “Paris was the worst person in the world for me to hook up with. [She] fed my worst impulses as far as partying,” a backhanded way of acknowledging his troubles with alcohol while still laying blame on her.
Hilton also dated Josh Henderson from Desperate Housewives, who never met a hoodie-blazer combo he didn’t like. She spent a few months in 2007 looking bored at clubs with the perma-stubbled actor. The only cultural critique to make here is that sometimes Paris Hilton liked sleeping with guys with abs, which isn’t a cultural critique at all.
Nevertheless, once we rolled into the 2010s, Hilton’s cache dwindled. The Simple Life was long gone, as were her friendships with Lohan, Nicole Richie, Britney Spears and the rest of her Hollywood party posse. Though Hilton would make waves from time to time — a cocaine arrest here, a mildly notable breakup there — she largely dissipated from national attention, due to the decline of gossip blogs, New York tabloids and overall Paris Hilton fatigue. Besides, how could she top her romp through the early aughts?
In 2018, Hilton broke off her third engagement, to The Leftovers actor (and conventional hunk) Chris Zylka. Her reasoning, while fair, sounds like an echo of 2006: “I’m just really having my ‘me time.’”
Some things, it seems, never change.
