When Sex and the City first premiered in the late ’90s, it was a refreshing encapsulation of the trials and tribulations of modern women, as represented by the lives and loves of four very different women living in New York City. Much has changed in the more than two decades since the show’s premiere; its nuances can be debated ad nauseam on the internet, and new generations can be introduced to its many eccentric characters.

Unsurprisingly, a compilation including the best characters on the series will have changed over time, with people like Carrie Bradshaw, once the main character of the series and possessed of a devoted fanbase, now becoming less popular than the cynical realist Miranda Hobbes. Just as in real life, the best characters prove not to be the most likable people, but the ones who are the most compelling.

10 Enid Frick

A precursor to Meryl Streep’s devilishly excellent Miranda Priestly character in The Devil Wears Prada, Candice Bergen’s Enid Frick was Carrie Bradshaw’s editor at Vogue. Enid initially seemed to represent the woman that Carrie could become, but viewers learned that instead, Enid represented all of the expectations that were holding her back.

The character wasn’t in more than a handful of episodes in the later seasons, but she was given depth and complexity, especially by the vulnerability that emerged from her icy façade when Carrie learned her husband was a serial cheater. She acted as a cautionary tale for Carrie, and indeed for many women at the time feeling the pressure to maintain both successful careers and relationships.

9 Richard Wright

The male embodiment of all of Samantha’s worst traits, Richard Wright was selfish, egotistical, and vain, but that didn’t mean he wasn’t a compelling character — or an exciting lover. The hotel magnate was a highly influential man in New York City, and for a time, he was one half of a power couple with Samantha.

That the series decided to show not only his crass apathy when he was on top of the world, but also his delusional sense of self-importance when he was no longer relevant, meant that “Mr. Wright” got to have a more complete narrative arc than many of the other minor characters on the series. He was a villain viewers loved to hate, especially for what he put Samantha through, but he seemed to relish every minute of it.

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8 Anthony Marentino

Not only was Sex and the City steeped in gay culture, it was also avidly watched by members of the LGBTQ+ community. Though it was rife with cultural stereotypes and tropes for its time, there was no denying that Anthony Marentino embodied a certain flavor of man keeping the city fabulous.

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In contrast to Carrie’s BFF Stanford, Anthony wasn’t afraid to tell Charlotte exactly how she looked in a dress, or what he thought about her sex life, or what he thought of her prospective partners. His words could be harsh, but his caustic one-liners made for some of the most entertaining quotes in the series.

7 Harry Goldenblatt

Harry Goldenblatt was an unlikely suitor for “Park Avenue Princess” Charlotte’s affections. He sure was a far cry from her dashing first husband, Trey MacDougal. Regardless, Harry was honest, funny, and adored Charlotte.

Harry’s contribution to the series, especially in its second half, can’t be discounted. Unlike Aidan Shaw, whose laconic charms only seemed to drag the girls down, Harry was low maintenance without being a wet blanket. He could have a beer with Steve and Big, which made him a perfect match for Charlotte and a fun, unpredictable member of the group.

6 Charlotte York

Charlotte could be somewhat of a divisive character for viewers, especially considering her narrow world view, myopic traditional values, and head-in-the-clouds sense of romanticism. However, her enduring belief in fairytale endings and happily-ever-afters won her the sort of fans who didn’t let urban cynicism get them down.

One of the characters who underwent the most growth out of anyone in the series, Charlotte managed to maneuver through situations that made her uncomfortable while maintaining her principles. She showed viewers that dreams really could come true when expectations were put aside.

5 Steve Brady

Humble bartender from the Bronx, Steve Brady was the unlikely boyfriend-turned-husband of the no-nonsense Miranda Hobbes, and a much-needed dose of reality the a series. While Miranda was obsessed with her work and joining the girls at the hottest spots to get a drink in New York City, Steve was there to remind her to enjoy the simple pleasures in life.

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Steve wasn’t always the most observant or the most considerate of men on the series, but he was there for Miranda when it counted. He demonstrated time and again that for love to be true, two people had to show up for each other. Not only were he and Miranda a good romantic couple, they were an effective team.

4 Carrie Bradshaw

Though she was the main character in the series, Carrie Bradshaw wasn’t always the most relatable. She could be neurotic, melodramatic, and naïve, but despite her more unsavory traits her quirkiness was infectious. Viewers may not have always liked Carrie’s choices, but they couldn’t help but root for her.

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Carrie ultimately had to find a balance between being a realist and a romantic, two sides of herself that were often in flux. Her free-spirited ways in the face of life and love’s adversities captured the essence of the era’s modern woman, and she would become forever iconic because of it.

3 Miranda Hobbes

Initially, Miranda Hobbes might have rubbed viewers the wrong way with her cutting sarcasm and straight-to-the-point analysis of even the most frivolous brunch talk. Over time, however, Miranda became (and remains) one of the most popular characters in the entire series because of her unwavering authenticity.

Miranda was always candid about what she thought of the expectations of modern women, and despite it all she still proved that she could have everything that she wanted in life — on her terms. Miranda went through some of the most challenging scenarios of any character on the series and handled them with integrity and strength.

2 Mr. Big

There isn’t a character on the series as controversial as Mr. Big, Carrie Bradshaw’s on-again, off-again lover who was at once emotionally unavailable and carnally overwhelming. Seen as a narcissist by many fans when his fear of commitment forced him to manipulate Carrie’s feelings, others saw him as the only adult in the relationship.

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One the surface, Big was a man who was used to getting his way and came off as selfish when he didn’t, but he’d also been hurt many times before, and his age predicated that not every frenetic freak out of Carrie’s deserved a 3AM conversation. Whether fans considered him a rogue or Prince Charming, his screen presence was nothing if not memorable and iconic.

1 Samantha Jones

Even more than Carrie Bradshaw, Samantha Jones has come to represent what Sex and the City was all about. Confident, stylish, and unabashedly herself, Samantha proved that women could do everything men could, from the way they had sex to the way they did business, and take enjoyment from their successes.

For one of the most shallow members of the group, Samantha was forced to become very humble towards the end of the series when she was diagnosed with cancer. In true Samantha Jones fashion, however, she came out the other side a more nuanced character while still true to herself.

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