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A Tribute to ‘Sex and the City,’ the Early Years

Remember those random man-on-the-street interviews and fourth-wall breaks? They were secretly the best part of the show.

The cast of ‘Sex and the City’ HBO/Ringer illustration

There are certain iconic images that come to mind when one mentions Sex and the City: the central foursome swapping NSFW stories around the brunch table; Mr. Big’s shit-eating smirk; Carrie Bradshaw staring into space over a hilariously bulky computer, struggling to form a sentence that will almost certainly begin with “I couldn’t help but wonder …”

What does not come to mind is a beautiful British journalist named Elizabeth falling in and out of love in under 30 seconds of screen time—though technically, she appears on screen before Carrie in the HBO series’ 1998 pilot, which aired 20 years ago this week. Even the most avid superfan doesn’t reminisce about Elizabeth venting to Carrie over coffee in a dingy Manhattan diner, acting as a source for her infamous New York Star column. Carrie Bradshaw, she of the weekly musings that somehow pay for an entire Upper East Side apartment, doing journalism! Perish the thought.

Sex and the City took its name from a New York Observer column written by Candace Bushnell that ran from 1994 to 1996 before being anthologized into a book of essays. (The show would last twice as long as its inspiration, turning a regional inside language into an international export.) The show’s early stylistic quirks—fourth-wall breaks, interviews, freeze-framed subtitles—are a clear attempt by creator Darren Star to mimic the rhythms of a reported dispatch. Bushnell’s writing is quite different from the series, even at the series’ inception: Where the show is suspiciously light on drugs for an ensemble with so many 40-something finance bros, Bushnell’s Miranda is a cable executive with a coke habit; tellingly, Charlotte, the most idealistic and prudish of the core four, is a creation native to HBO.

When Carrie first introduces herself to Big, she describes her profession as “sexual anthropologist.” Thanks to the title of the show and the direction of its later seasons, the first half of that phrase is well-integrated into our understanding of the character and the series she narrates. It’s the second half, however, that delineates Sex and the City’s early era from what followed. Anthropology certainly seems like the goal of the simulated man-on-the-street interviews—though as the show’s star rose and its budget increased, these interludes were dropped in favor of a more conventional structure. To be honest, this is the part of the show I’ve always liked the most: Before Steve and the kids, before Trey, before Brooklyn or Aidan or Vogue, there was a broad, pseudoscientific, almost mockumentary attempt to come to grips with dating in nearly-21st-century New York. The fake interview subjects helped maintain the illusion that Sex and the City was more survey than story.

Sex and the City’s first episodes hew much closer to Bushnell’s column in both form and exploratory spirit. In seasons 1 and 2, the pun-laden questions Carrie poses in voice-over aren’t purely rhetorical: They’re conversational prompts, and they’re answered with responses from a cross section of New Yorkers that often has all the diversity the core cast conspicuously does not. The implication is that Carrie has conducted all these interviews in her quest to understand the unspoken mores of modern love, though with very few exceptions, we never see these conversations actually being conducted. Instead, they’re presented as updates from the city itself, with individuals holding forth while the hustle and bustle continues indifferently around them.

In the pilot, Carrie offers a tour of “Toxic Bachelors,” a taxonomic designation in the vein of Bushnell’s “Psycho Moms” and “Bicycle Boys.” (A different Bushnellism, the phenomenon of “Modelizers,” would become the theme of another Season 1 episode.) Toxic Bachelors are almost entirely macho white men, and we watch them explain the midlife New York dating scene from their perspective. Advertising executive Peter Mason coins the phrase “mid-30s power flip”; Skipper Johnston, an adorkable dweeb with the nebulous designation of “website creator,” complains that women only like bad boys. Skipper will later have an ill-fated dalliance with Miranda that reveals him to be a creepy, entitled nice guy a full decade and a half before the nice guy complex became widely derided. Sex and the City’s ironic cocktail of prescient and retrograde never ceases to confound.

Another episode follows Carrie and Samantha’s experiments in dating younger men and shows them all in a pickup basketball game at the court at the West 4th Street Courts. Rich Stein (stock analyst), Jake Lewis (bass player/dog walker), and Fred King (high school senior) each offer their thoughts on dating older women in a scene much more stylistically playful than Sex and the City is generally known for. (The first season boasts a formidable directors’ roster, much of it female, including Susan Seidelman, as in Desperately Seeking; Alison Maclean; and Nicole Holofcener.) The game acts like an animated focus group, illustrating the guys’ youthful exuberance at the same time they’re testifying to it. These are boys, not men, with the schoolyard antics to show it.

These interstitials were frequently used to pull in perspectives that wouldn’t overlap with the main story line quite so organically. In the second season premiere—the one where Carrie and Co. iconically attend a Yankee game in coordinated sunglasses and furs—our antiheroine contemplates how to recover from what would become the first of many breakups with Big. A fellow spectator chimes in; so does a concessions saleswoman hiking the steps of Yankee Stadium; so does an actual Yankee. Carrie dates a Yankee, of course, but neither the fellow fan nor the popcorn hawker look anything like the well-groomed glamorati that populate the rest of the show. It’s nice to see that the rest of the city is having sex, too.

It’s easy enough to understand why the writers phased the interviews out entirely by the end of Season 2. TV is built on familiarity and intimacy between the audience and richly developed protagonists. Why waste time on a throwaway character when those precious seconds could be better spent on innuendo-laden banter? So Sex and the City became more about Carrie, Miranda, Samantha, and Charlotte, and less about the dating scene the group initially served as conduits to. The show followed them into marriage, motherhood, and dream jobs, leaning ever further into glitz, fantasy, and wish fulfillment. (Not that Sex and the City wasn’t always a fantasy: The first words of Carrie’s first-ever monologue are “Once upon a time …”) We want good things for those we love, so Carrie got $4 a word at a major magazine and Miranda a sweet, supportive partner to raise her kid.

But the show nonetheless lost something when it stopped trying to faithfully document a vast swath of urban existence. The same principle holds for the revolving door of guys—four per episode—the quartet cycled through in full singledom. Settling down with Big, Steve, Harry, and Smith meant ceasing to demonstrate the extraordinary variety of heterosexual male douchebags. (Tragically, it also cut down on the cameos from future stars like Will Arnett and Justin Theroux.) By going all in on depth, Sex and the City ceded some of its breadth. Thanks to HBO’s liberating lack of censors, the show never stopped being about sex—but its earliest iteration felt more of the city.

Disclaimer: HBO is an initial investor in The Ringer.