“Masquerade”: A 1988 Mystery Film Shot in the Hamptons

With the sun setting well before 5 p.m. now that Daylight Savings Time has ended, East Enders are spending more time indoors. Some escape their computers and smartphones by watching classic films on television. Many locals enjoy movies filmed in the area where they live. One such film, Masquerade, was shot exclusively on the East End in 1988, particularly in Sag Harbor, Southampton Village, Shelter Island, Riverhead, and at the Dennistoun M. Bell estate in Amagansett.

For locals and summer visitors alike, it’s a thrill to see the Hamptons as they were in 1988. The scenes in Southampton Village are mesmerizing, and Shelter Island looks almost the same today as it did nearly forty years ago. Watching Masquerade, you’ll likely find yourself thinking, “I know that spot, that location, that beach.” There will be plenty of those moments.

This romantic thriller with a surprising twist stars Rob Lowe (in his twenties), Kim Cattrall (31 years old), Meg Tilly, Doug Savant, Dana Delaney, and even Boz Scaggs, who plays a police officer. The movie was written by Dick Wolf (best known for Law & Order) and directed by Bob Swaim. The cinematography is exceptional, capturing the bright beauty of summer on the East End.

Rob Lowe plays a hired racing yacht captain for a wealthy sailboat enthusiast who doesn’t realize his wife (played by Kim Cattrall) is having an affair with Lowe. Enter Meg Tilly, a wealthy orphan who sparks a romance with Lowe, and the drama unfolds, full of posh parties, beautiful people, and the high society of the Hamptons. There are also plenty of moments with the locals—doing what locals do and say. On top of that, the movie showcases the stunning reality of summer in the Hamptons, including exciting sailing scenes. The racing yacht scenes in Shelter Island’s Dering Harbor are particularly well done, and the Shelter Island Yacht Club plays a prominent role in the film. After watching it, you’ll never look at that facility the same way again.

Masquerade earned $15,855,828 at the U.S. box office, and Rob Lowe himself has said in his autobiography that the movie “bombed.” According to a Variety article, Lowe recalls Dick Wolf’s frustration at the time: “I remember him saying to me how frustrated he was in the movie business, that he was going to write a pilot, and he wrote Law & Order. And the rest is history. You’re welcome. Yeah, I’m happy to provide the bomb that powers your rise to dominance.”

The movie features many of the twists and turns that would later make Law & Order so successful. There are several theories about why Masquerade didn’t resonate with audiences. One theory is that it contained too many explicit sex scenes, which were frowned upon by some critics. The movie was released during the Reagan era, amidst cultural battles that affected the reception of films. It was rated R in the U.S., which likely didn’t help its popularity. Additionally, in the 1980s, the Hamptons were not as widely known as they are today. Back then, large summer homes could be rented for just $10,000 for the entire season.

At the time, Rob Lowe was tabloid fodder as part of a new “young rat pack,” something that elite critics dismissed as eye candy, not the serious acting of stars like Dustin Hoffman or Paul Newman. Still, renowned film critic Roger Ebert gave the film three stars, praising Meg Tilly’s performance: “…the right choice for the movie: Her dreaminess, which at first seems distracting, becomes an important part of the suspense. While she drifts in her romantic reverie, a sweet smile on her face, we’re mentally screaming at her to wake up and smell the coffee.”

So why should you watch Masquerade? First, it’s a great who-done-it mystery movie. Second, it offers a nostalgic glimpse of the Hamptons in 1988 (you might even recognize some of the extras!). Lastly, it’s fun to see Rob Lowe and Kim Cattrall in their younger days, before they became icons in The West Wing and Sex and the City.

Next time you’re wondering, “Maybe a movie tonight?” head over to Amazon Prime Video and give Masquerade a shot. It’s well worth the effort.