South O’ the Highway 2021 Year in Review: Hamptons Celebrity Gossip by the Month

Hamptons celebs kept the gossip flowing in 2021 - South O' the Highway year in review
Hamptons celebs kept the gossip flowing in 2021

Over the past 12 months, and year two of the pandemic, the media has been dominated with stories about the culture war, clashing ideologies, and the continuing cancel culture fallout. Thankfully, our favorite celebrities and socialites continued to provide a vicarious escape. From the ocean beaches to local restaurants, to parties by the pool, the resilient residents of the Hamptons kept on moving, and the gossip kept flowing.

Let’s take a look back at a some of our top South O’ the Highway stories and other monumental Hamptons events from 2021.


Sports merchandise mogul Michael Rubin bought a $50 million mansion in Bridgehampton previously owned by HFZ Capital Group.

“I was like Vincent van Stern over here,” Hamptonite Howard Stern said as he talked about his Dan’s Papers cover on The Howard Stern Show, his hugely popular radio program. Stern discussed how the exciting cover came to be and explained that he asked that it be on the December 18, 2020 issue when we interviewed his wife, Beth Ostrosky Stern, about her animal advocacy. “The only thing that was in the house to read [during the pandemic] is Dan’s Papers, a local paper out here where I live,” Stern said. “I always said to my wife, ‘I wish my painting was on the cover,” the iconic radio personality continued, adding, “I’ve had some accomplishments in my career — I’ve made a film, but this more exciting to me than anything, that one of my paintings would be on the cover of Dan’s Papers. I don’t know what I thought would happen, but I was excited about it. It was kind of my debut!” Stern painted his second Dan’s cover for the July 16, 2021 issue. Listen to The Howard Stern Show on Sirius XM, and let’s hope we see Stern back on the cover soon!

In a bit of odd news, Hamptonite Jane Krakowski had to shoot down a strange rumor that the Dickinson actress — a liberal LGBTQ advocate and star of numerous comedic television shows and films — was having a secret affair with MyPillow CEO and far-right activist Mike Lindell. Krakowski’s representation debunked the story to Vanity Fair, noting cheekily, “Jane has never met Mr. Lindell. She is not and has never been in any relationship with him, romantic or otherwise. She is, however, in full-fledged fantasy relationships with Brad PittRegé-Jean Page, and Kermit the Frog, and welcomes any and all coverage on those.”

Jane Krakowski did not have an affair with MyPillow CEO Mike Lindell
Jane Krakowski did not have an affair with MyPillow CEO Mike LindellREUTERS/Mario Anzuoni


News broke that Hamptonite Mariska Hargitay would reunite with longtime co-star Chris Meloni in a special episode of Law & Order: Special Victims Unit on April 1. The special saw Hargitay’s Olivia Benson and Meloni’s Elliot Stabler onscreen together for the first time since Meloni left the show in 2011.


Southampton’s Brooke Shields spoke to People about being badly injured in a January accident. “It felt like it was all in slow motion. And then I just started screaming,” Shields told the outlet. The actress fell off a balance board at a Manhattan gym in January and suffered such severe injuries that she was hospitalized for two and a half weeks. “Sounds came out that I’ve never heard before,” she added. Shields underwent two surgeries to insert several metal rods and a metal plate to repair her hip and femur. But by summer, she was back out and about.

Jimmy Fallon and Alfredo Merat sing "Guantanamera" at Old Stove Pub in Sagaponack
Jimmy Fallon and Alfredo Merat sing “Guantanamera” at Old Stove Pub in SagaponackInstagram/Merat


Sagaponack’s Jimmy Fallon had an impromptu “Guantanamera” singalong with beloved local singer-songwriter Alfredo Merat at Old Stove Pub on April 16. Merat posted the video of the moment on Instagram. It was not the first, or even the second, time Fallon has been filmed singing at a local bar or restaurant.


New England Patriots owner Robert Kraft bought a $43 million mansion in Southampton.


Rapper Flo Rida was spotted giving live performances on June 6 at Blu Mar and Buddha Lounge in Southampton.

According to Roger Friedman‘s Showbiz 411, Martha Stewart celebrated “taking leave of the Hamptons once and for all” by hosting a major A-list Southampton book party for Pulitzer Prize-winning historian and architecture writer for The New York Times Paul Goldberger at the historic Atterbury Estate. Stewart’s home, listed for $8.4 million, was snapped up by former Huffington Post investor and publisher Buzzfeed chairman Kenneth Lerer and his wife, interior designer Katherine Sailer, for $16.5 million —double the asking price.


In Bridgehampton, Michael Rubin, the co-owner of the Philadelphia 76ers took a page out of East Hamptonite Sean “Diddy” Combs‘ book and threw a blow-out Fourth of July white party, where Jay-Z pulled up in a Rolls-Royce, Alex Rodriguez flew in by helicopter and the guest list included Beyonce, Jon Bon Jovi, Emily Ratajkowski and Megan Thee Stallion. A few weeks later, Rubin’s friend Robert Kraft celebrated turning 80 at a surprise party his sons threw for their father in the Hamptons. The party was attended by some of the biggest celebrities in the world. Lionel Richie provided the music, while David Spade performed some stand-up comedy. Adele, NFL Commissioner Roger Goodell, Jon Bon Jovi, Meek Mill, Kenny Chesney and Billie Jean King were all in attendance.

Ben Affleck and Jennifer Lopez canoodling in 2003 Bennifer
Ben and Jen in 2003©Patrick McMullan

The Bennifer reunion tour definitely ranked among the biggest celebrity events of the year. Seventeen years after they called it quits in 2004, Water Mill’s Jennifer Lopez and Ben Affleck returned to each other’s warm embrace in April following an extended period of love letter writing that started in February. And, as we predicted, the Bennifer lovefest eventually landed in the Hamptons. On Saturday, July 3, Jlo and Affleck were spotted taking a loving walk near her Water Mill estate. According to spywitnesses, the coo-some twosome strolled through the streets with “their arms wrapped around each other.” Page Six reported that the duo spent the day with their kids at Universal Studios Hollywood on July 2 before flying across the country for their big Hamptons weekend. They’re still together and have reportedly been making an effort to integrate their families more over the holidays.

Tom Ford AW/20 Fashion Show
Miley CyrusDavid Crotty/PMC/PMC


Miley Cyrus made a rare appearance in the Hamptons on August 1 when Bitcoin billionaire Michael Novogratz hired her to play an over-the-top private birthday celebration concert for his daughter, actress Gabriela Novogratz. The loud event ruffled more than a few neighbors’ feathers. Maybe he should have invited them.

During another superstar visit in mid-August, Kendall Jenner and her boyfriend, Phoenix Suns shooting guard Devin Booker, hit the Hamptons with a vengeance. The couple made stops at Cittanuova in East Hampton and 75 Main and Dopo Argento in Southampton to celebrate the launch of Jenner’s 818 Tequila. They kept the party going the next day at various Montauk hotspots, then finished the trip on day three at Sunset Beach on Shelter Island.

Kendall Jenner at Sandbar in Montauk
Kendall Jenner at Sandbar in MontaukCourtesy 818 Tequila


East Hampton superstar couple Beyonce and Jay-Z enjoyed an end-of-summer trip cruising the Mediterranean on the 450-foot-long superyacht, Flying Fox. The massive yacht costs nearly $4 million per week to charter, according to Forbes, and Bey and Jay posted plenty of pics on Instagram to chronicle their luxe vacation.

Ina Garten
Ina GartenCourtesy Food Network


Ina Garten, the chef known as the Barefoot Contessa, expanded her work for Discovery and Food Network beyond her popular program under the terms of a new multi-year deal. The author of 12 cookbooks and the host of Food Network’s Barefoot Contessa, Garten will start work on a new series, Be My Guest, which is in development for 2022 and is structured so that each episode has three different versions: an hour-long cut for use in the streaming platform Discovery+, a half-hour version for the Food Network channel and a companion podcast. Episodes will be filmed on location at Garten’s East Hampton home. “I’m so looking forward to filming new shows,” Garten said in a statement announcing the deal. “With Be My Guest, I’m welcoming really fun, interesting people into my barn in East Hampton for good food and conversation. This is going to be so much fun.”


Amagansett super chef Bobby Flay butted heads with Food Network over his contract in October, but they eventually came to financial terms in late November. The Iron Chef and tv host signed an exclusive pact that will keep him with the Food Network through 2025 and up to his 30th anniversary on air with the cable network.

Southampton’s Paris Hilton married author Carter Reum in a lavish November 11 ceremony that made headlines all over the world. Not only were the likes of Kim Kardashian and Nicole Richie on the guest list, but Paris wore a bespoke Oscar de la Renta gown that took months to make. Meanwhile, her mother, Kathy Hilton recently tweeted out that she has returned to filming the Real Housewives of Beverly Hills.

Paris Hilton and Carter Milliken Reum in wedding style outfits
Paris Hilton and Carter Reum conjure wedding vibes at LACMA on November 6, five days before they tied the knotRobert Smith/PMC


Amagansett resident Alec Baldwin took three of his children to enjoy a chilly visit to the beach at Little Alberts Landing on December 19, reports the Daily Mail. The family left Manhattan on December 17 after Santa Fe sheriffs issued a search warrant for Baldwin’s iPhone in their investigation into the tragic accidental shooting death of Halyna Hutchins on the set of his film Rust in October. The family has been in East Hampton since the 17th when Baldwin was spotted outside his Manhattan home packing up his Cadillac Escalade with Christmas wreaths, bags and presents.

Andy Cohen and Anderson Cooper return for CNN’s New Year’s Eve Live Courtesy CNN Press Room
Andy Cohen and Anderson Cooper return for CNN’s New Year’s Eve LiveCourtesy CNN Press Room

On the December 20 episode of Radio Andy, Andy Cohen‘s SiriusXM radio show, People reports the Amagansett resident talked about his bout with breakthrough COVID, explaining that he had to separate from his 2-year-old son Benjamin for 10 days while isolating. “I quarantined in the house. The first day was really rough and he was really upset and he wanted to hug me so badly,” Cohen told his co-host John Hill. “Thankfully, what wound up happening was we tried cohabitating and he was not getting the message that he could not come near me and it was serious. It was really upsetting. And he wound up going out to Long Island with his nanny.” Father and son have since reunited. And, of course, Andy and his pal Anderson Cooper, formerly of Quiogue, will ring in 2022 as they host CNN’s New Years Eve Live festivities at Times Square on Friday night.

Happy New Year!

Additional reporting by Oliver Peterson

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