Anders Hill worked on Wall Street, and lived in Westport. He left his job — and his wife — for unclear reasons. He hooks up with women, has issues with his kids, and muddles through his middle-aged life.

Anders Hill is not a real character. But he’s not entirely made up, either. He’s the protagonist of Ted Thompson’s first novel, “The Land of Steady Habits.” Thompson — a 2001 Staples High School graduate — looks at the hometown that gave him tremendous opportunities with a Cheever-esque eye for the life lurking beneath the suburban surface.

Now “Steady Habits” is a feature movie. Released by Netflix, directed by Nicole Holofcener and starring Ben Medelsohn and Edie Falco, it earned a positive review from New York Times critic A.O. Scott.

The trailer shows a sunny view of Main Street. But this is not a feel-good film. Scott calls “the darkness and pain haunting Westport” as “pronounced.”

This is not the first time Westport has taken a star turn on a Hollywood screen. And — like several predecessors — it is not a portrayal that realtors or the Chamber of Commerce will highlight on their websites.

The prototypical Westport film is “The Man in the Gray Flannel Suit.” Released in 1956 — a year after Sloan Wilson’s novel by the same name — it featured mega-star Gregory Peck as Tom Rath. As post-war suburbia boomed, he tried to balance his marriage, family and job. Moviegoers around the world saw images of Main Street and the train station — and realized that behind the façade of prosperity, dinner parties and white picket fences was a not-so-wonderful life.

A dozen years later, “The Swimmer” offered a similarly un-sunny view of suburban life. Burt Lancaster starred in the adaptation of John Cheever’s short story. As he swims his way through Fairfield County pools, Ned Merrill’s life is a mélange of sex, alcohol and disappointment.

“The Swimmer” was filmed partly in Westport. Its pools looked beautiful. Its message was anything but.

The hits just kept on coming. In 1972, Ira Levin’s novel “The Stepford Wives” introduced a new term into the American lexicon. Three years later, a movie version cemented the image of beautiful suburban women who are obsessed with housework, have few real interests, and not only act like — but really are — robots.

“Stepford Wives,” like other Westport-based movie adaptations, was also filmed in part here. More than four decades later, it remains a cult classic. And its name lives on, as shorthand for the vacuity of suburban life.

Movies are not the only popular medium to give broad audiences a less-than-ideal image of Westport. “American Housewife” is now in its third season on ABC. The premise is intriguing — in an affluent town like this, a less-than-perfect family can thrive — but really it’s just another sitcom. Katie Otto’s family is not really “flawed.” And though she believes her less-than-ideal weight separates her from the rest of Westport’s women, she’s hardly obese.

The fact that the show’s original title was “The Second Fattest Housewife in Westport” is not exactly a reason to cut a celebratory cake, either.

Over on Showtime, Damian Lewis has spent three seasons intriguing viewers as Bobby Axelrod, the billionaire brains behind the Axe Capital hedge fund. His character is based loosely on Steve Cohen of the former SAC Capital, but the fictitious firm is based in Westport (a not-so-subtle nod to Bridgewater Associates). There are occasional references to our town, along with shots of extremely large houses and winding roads. Of course, Bobby has a house in the Hamptons too.

Not all movie and television images of Westport involve money, alcohol or debauchery. In 1958, “Rally Round the Flag, Boys!” told the tale of Putnam’s Landing. Like Westport, the fictitious town was torn by the imminent arrival of a missile base.

The film was adapted from a novel by Max Shulman — a Westport resident who had a ringside seat to the real debate. The movie may not be remembered much today. But it starred Paul Newman and Joanne Woodward. Their introduction to our town was positive: They moved here shortly thereafter, and never left.

Like Shulman, “Twilight Zone” creator Rod Serling was a 1950s-era resident. In “A Stop at Willoughby” a harried advertising executive heads home to Westport — and somehow finds himself back in 1888, a much simpler time.

The same 1950s — seen by us today as a simpler time too — was when Luci and Ricky Ricardo joined Ethel and Fred Mertz as Westport homeowners Westport, in the final season of “I Love Lucy.” A few years later on “Bewitched,” Darrin and Samantha Stephens lived here, at the very fictional 1164 Morning Glory Circle.

That’s a brief movie and TV history of Westport, Connecticut. Or, as our state is sometimes known, the “Land of Steady Habits.”

Dan Woog is a Westport writer, and his “Woog’s World” appears each Friday. He can be reached at His personal blog is