Who’s Afraid Of Scary Island?

Much like pornography, you know Scary Island when you see it. The 2010 Real Housewives of New York episode (officially titled “Sun, Sand and Psychosis”) aired in the middle of the series’ third season, sandwiched within a three-part arc set in the Virgin Islands. But to real RHONY fans, it’s the watershed moment of the entire franchise.

“Scary Island was something that people had always talked about so I was looking forward to it. But I was like, ‘How will I know when it's Scary Island?’” Hung Up’s Hunter Harris, who watched the series for the first time last year, tells me. “Then I was watching the episode and I was like, ‘Wait, this has to be Scary Island, because this is the craziest thing I think I've ever seen in my whole life.’”

While it’s impossible to describe the events surrounding Scary Island and actually do the phenomenon justice, here’s a quick recap: Tensions had been building between Bethenny Frankel (who, at the time, was the show’s bootstrapping “underdog” and Bravo’s golden girl) and Kelly Bensimon (the former model and ex-wife of famed French photographer Gilles Bensimon, who was far from a fan favorite). It all came to a head on the trip, when Bensimon confronted Bethenny and wound up melting down in… unprecedented fashion. As Bensimon herself said, in the iconic line that would give the episode its unofficial name, “I’m here by myself. I’m alone on Scary Island.”

“You literally could see Kelly unraveling before your eyes, and that's why it's scary,” says RHONY’s Sonja Morgan, who watched it happen live. “And then you also see Bethenny losing it.”

Here, on the 15-year anniversary — with both the benefit of hindsight and new insights from RHONY cast members and commentators — is a look back at what, exactly, made Scary Island so singular.

What Fans Saw

When Ramona Singer invited castmates Alex McCord, Morgan, Frankel, and Bensimon to cross international waters to celebrate her 17th wedding anniversary (because… sure), expectations were tepid. “There was this thought that our New York cast was going to be buttoned-up, careful, and not as crazy,” journalist Jessica Pressler, who wrote recaps of the series for New York, says of the show’s early days.

And at first, things were smooth sailing. The girls had a yacht day, Bensimon staged a beachside photo shoot, and Frankel, who’s a trained chef, offered to cook for the women at the villa. But after Frankel left a swag bag full of Skinnygirl merch for Bensimon in her room — prompting her to accuse a pregnant Frankel of everything from having “knives on her tongue” to having tried to kill her “many times before” — all pretense was stripped away. “It was chugging along at that point but [the episode] was so wildly entertaining that I feel like it made Real Housewives of New York into a ‘thing,’” Pressler says. “After that recap, more people in my real life engaged with me about it and wanted to talk about how crazy Kelly was.”

It wasn’t so much the insults Bensimon hurled at Frankel that galvanized viewers, but rather the series of non-sequiturs and asides that she accompanied them with. As the two sparred off over dinner, the model also managed to bring up her “friend Gwyneth Paltrow,” offered the other women a “jellybean or a lollipop,” and asked Singer and Frankel if they were going to “make out with the tongue.” (In 2021, Paltrow appeared on Watch What Happens Live and demurred when Andy Cohen asked if she actually had a friendship with Bensimon.)

Frankel’s retort to the tirade was a simple yet effective, “Go to sleep, go to sleep!” Whereas all Singer could focus on was her next glass of pinot grigio. (Which she received via a disembodied hand — a shot that became the definitive IYKYK moment of the episode.)

As for Bensimon? She’d high-tailed it out of there by the following morning. And while the remaining housewives awoke to a whole new horror — by way of their frenemy Jill Zarin showing up to the villa, unannounced and uninvited — Bensimon was already back in Manhattan doing damage control.

Yet no matter how she tried to spin things, once the episode aired, only one narrative stuck: that Bensimon was, as Frankel put it on the episode, “cuckoo for Cocoa Puffs.” Journalist Brian Moylan, author of The Housewives and longtime chronicler of Bravo, recalls discussing Bensimon’s meltdown in the Gawker newsroom. “I remember Richard Lawson was recapping the show at the time and I was trying to convince him to make the headline ‘RIP Kelly Bensimon,’” he says.

Bensimon was all too aware of the chatter. “It’s not easy to come back from crazy, Andy,” Bensimon said on WWHL. “Like that doesn’t brand well. I was toxic. You couldn’t touch me.” (Bensimon didn’t respond to multiple requests for comment.)

What Fans Didn’t See

Out to sea, Bravo also found themselves out of their depths. Production has since admitted they were “seriously understaffed” for their first-ever international trip — it was all-hands-on-deck, even without the full cast to wrangle.

In fact, the absence of cast members like Countess Luann de Lesseps arguably made things worse. “Kelly didn't want to go without me or Jill [Zarin], her backers, and I told her, ‘You will not survive without me,’” says de Lesseps. “But I'm so glad she did because it wouldn't be Scary Island if I was there. I would never let that go down.”

De Lesseps attests that the fear Frankel put into the other women was very real. “Bethenny had it in for [Kelly] and most women cannot handle the thrash of Bethenny. I can deal with her. Use the example of our fight in the Berkshires. She went after me and I just said, ‘You need to get laid, girl,’” she says. “But Kelly, the gorgeous and fabulous woman that she is, isn’t equipped for this kind of scenario. She was texting me from afar [that night] and I said, ‘Just take a deep breath, don't let them get to you because they will.’” (Frankel declined to comment for this article.)

For her part, Morgan was bewildered by Bensimon’s outburst. “I was new to the scene on Real Housewives of New York, and I really didn't know what I was in for, because I'd known all the girls before filming the show. And I had never seen Kelly behave like that ever in my life,” she says. “I was like, ‘Girls, she needs help right now. We don't need to make this worse.’” Ultimately, Morgan was so disturbed that she decided to sleep in Singer’s room that night: “The rooms had sliding doors and I only had one umbrella and I needed two [to barricade myself]. So I took mine and went over to Ramona's room and we wedged our umbrellas together. Then ever since that trip, we always shared a room.”

RHONY producer Matt Anderson, meanwhile, understood there was much more of a method beneath Bensimon’s madness. “She was in the scene and she didn’t like where it was going, and so she just said my name over and over. She goes, ‘Matt, Matt, Matt, Matty, Matty,’” Anderson revealed on a panel at BravoCon 2022. That’s where Bethenny was like ‘Go to sleep!’” And while Morgan and Singer slept safely behind their umbrella barricade, Anderson set to work on setting Bensimon straight: “I went up to her room, and she’d actually, like, talked two other producers into letting her stay. They’re like, ‘I think she’s OK now.’ And I’m like, ‘No, I think it’s time to go home.’ ... So we sent her home. She quit the show the next day. And happily, she decided to do the rest of the season, but she was really upset with how things went.” (Andy Cohen declined to comment, via representatives for Bravo.)

What she’s trying to talk about is, “This is some bullsh*t, we’re all playing these parts.” But the other women just don't give into it.

What Bensimon appeared to be doing with her fourth wall-breaking moment — which production later edited around — was to put Frankel on notice. “Bethenny was the hero of the show. Bravo had invested a lot in her doing a spinoff, and the other women are all sucking up to her. But Kelly sees Bethenny: her game, her branded merch, and that Bethenny's trying to antagonize her and make her a villain,” Pressler says. But in doing so, she also isolated herself, as the other women played by Bravo’s rules, and refused to discuss the show on-camera. “What she's trying to talk about is, ‘This is some bullsh*t, we're all playing these parts.’ But the other women just don't give into it.”

What Fans See Now

These days, a multi-episode cast trip is as common in the Bravoverse as a poorly-executed theme party or an alcohol-fueled spiral. Yet it wasn’t until RHONY traded the island of Manhattan for that of St. John that these vacations became a tried-and-true staple. “Now, it’s like, ‘This is how we behave as Housewives. This is how we go on a trip.’ And as fans, it’s like, ‘They’re going on vacation, here’s what to expect,’” says Moylan. “But what led to this being such a great episode is that they're being so raw, real, and themselves in a way that I don't think we'll ever be able to fully recapture.”

In hindsight, even Frankel’s Skinnygirl shilling — which established socialite Bensimon found so gauche that it triggered… all of this — feels unforced and authentic in comparison to the QVC cosplay we now see on the franchise. “We didn't really realize that Bethenny was building her brand. It seemed so low-key, like, ‘Oh, she's proud of her business!’ Now people go on the show for the reason of promoting brands,” Pressler says. They also go on the show fully prepared to architect their own viral, Scary Island-esque moments — see: basically every act Monica Garcia committed on her season of Real Housewives of Salt Lake City — often leading to fourth wall-breaking fights. (Which, thankfully, Bravo now allows to remain in the edit.) “If it were now, Kelly would be saying to Bethenny, ‘You're trying to produce this moment.’ She'd use that kind of language.’”

Later, de Lesseps herself would attempt to produce Bensimon’s comeback. “I said, ‘I didn't like the way that went down for you, so let's reinvent you,’” de Lesseps says. And what better way for Bensimon to stage her grand return than appearing on the 2023 installment of Ultimate Girls Trip? “Andy said, ‘You know what, I love that because Kelly's done so much work on herself, got a real estate license, and rose from the ashes.’” Still, the stink of Scary Island continued to loom large while Bensimon filmed the new series in St. Barts with her former castmates — with Dorinda Medley even confronting her about it over dinner one evening. “This story never really left her side, which always upset me because she's not crazy. She's not equipped for that kind of drama,” says de Lesseps.

But if you ask fans about that season of Ultimate Girls Trip, they’ll tell you that getting the gang back together wasn’t enough to rekindle that Scary Island magic. In fact, among all of the Housewives trips that have come in its wake, Scary Island still remains by itself, alone in its superiority. “It wasn’t really a trip where everyone’s fighting or [acting] a little crazy. It was just the exact tinder box for one person, which is an unusual dynamic for a Housewives trip,” says Harris. “It’s just Kelly haunting the house, running around like she's trying to exorcise every single person's demons.”