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‘Sex and the City’: 6 Seasons of Boyfriends, Ranked Best to Worst

After 20 years, I couldn't help but wonder... who, really, was the ultimate trash?

No Merchandising. Editorial Use Only. No Book Cover Usage.Mandatory Credit: Photo by Craig Blankenhorn/Hbo/Darren/REX/Shutterstock (5886159bb)Cynthia Nixon, Kristin Davis, Kim Cattrall, Sarah Jessica ParkerSex and The City - 1998-2004Hbo/Darren Star ProductionsUSATelevision

“Sex and the City”

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In paying tribute to the 20th anniversary of the groundbreaking HBO comedy “Sex and the City,” it seemed like a natural fit to examine the boyfriends, husbands, and other partners on the show. While the series stands out as a tribute to female friendship, the love stories scattered across six seasons often offered a great deal of insight into Carrie, Miranda, Samantha, and Charlotte as well.

For the record, we’re not considering the two films in this ranking, because…. well, they’re bad. More importantly, what they add to the narrative doesn’t really have the same impact as watching these characters develop over the course of seasons; the films made an effort to cram a season’s worth of story into two hours.

12. Harry Goldenblatt (Evan Handler)

Harry was always unapologetically himself, and the way he tore down Charlotte’s defenses made their love story one of the show’s most relatable and heartfelt. While they did break up once before settling down together, the reasons for their breakup were totally justified, and the experience of losing Harry made Charlotte truly appreciate what they had, leading to a redemptive ending for the pair that was deeply affecting. Just watch the below as a reminder, and lie when you say that you didn’t cry. (Damn you, Badly Drawn Boy!)

11. Steve Brady (David Eigenberg)

No Merchandising. Editorial Use Only. No Book Cover Usage. Mandatory Credit: Photo by Hbo/Darren Star Productions/Kobal/REX/Shutterstock (5886159ax) Cynthia Nixon, David Eigenberg Sex and The City - 1998-2004 Hbo/Darren Star Productions USA Television

It took years for Miranda to come to terms with Steve’s place in her life — and her heart — but he proved to have the backbone to stick things out, even when they were simply co-parenting Brady Hobbes together. Steve’s presence in Miranda’s life transformed her from a lonely single woman to a truly loving wife and mother; she never stopped being herself, as her housekeeper Magda observed in the series finale, “What you did. That is love. You love.” And Steve’s love and patience with her was a crucial element of that.

10. Smith Jerrod (Jason Lewis)

No Merchandising. Editorial Use Only. No Book Cover Usage.Mandatory Credit: Photo by Hbo/Darren Star Productions/Kobal/REX/Shutterstock (5886159cd)Jason LewisSex and The City - 1998-2004Hbo/Darren Star ProductionsUSATelevision

A former addict/waiter whom Samantha ended up guiding into the spotlight, “Smith Jerrod” (AKA Jerry Smith) model-turned-actor was admirable for his no-bullshit approach to their relationship, as well as a clarity of spirit that helped him get under Samantha’s skin, especially during a particularly unsexy time in her life.

9. Maria Diega Reyes (Sonia Braga)

Samantha’s bisexual phase was short-lived, but Maria genuinely challenged Samantha more than sexually, which proved powerful after several seasons of watching her screw around with all the men of New York City. While it didn’t work out between the two of them, Samantha became a more open and vulnerable person as a result — Maria was ultimately the sort of partner that leaves you better than you were before and should be remembered fondly as a result.

8. John/Mr. Big (Chris Noth)

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On the one hand, Mr. Big really put Carrie through the wringer over the course of these six seasons, an off-and-on romance that verged on the unhealthy side of the spectrum more often than not. But he seemed to genuinely care about her right from the beginning, and more importantly liked her for who she was, at her core. The fact that he ended up being her ultimate choice wasn’t overplayed as a happily-ever-after, but rather confirmation that the real love story of the series was Carrie’s relationship with herself.

7. Trey MacDougal (Kyle MacLachlan)

No Merchandising. Editorial Use Only. No Book Cover Usage. Mandatory Credit: Photo by Hbo/Darren Star Productions/Kobal/REX/Shutterstock (5886159ci) Kristin Davis, Kyle Maclachlan Sex and The City - 1998-2004 Hbo/Darren Star Productions USA Television

Perfect preppy Trey, the first Mr. Charlotte York, was the very definition of “be careful what you wish for” — while Kyle MacLachlan was a hilarious addition to the series, the way their marriage ultimately collapsed was heartbreaking to witness, given how important getting married was to Charlotte. Their relationship, however, was an important step on her journey towards discovering that perfection isn’t exactly what it seems to be, and Trey gets points for (eventually) standing up to his overbearing mother on Charlotte’s behalf.

6. Skipper Johnston (Ben Weber)

A sweetheart on paper, the 20-something Skipper had the niceness that was a solid complement to Miranda’s rough edges, but ultimately wasn’t bold enough to truly challenge her. The way he was quietly dumped was more than enough proof that he lacked the staying power of some of the other fellows on this list.

5. Richard Wright (James Remar)

No Merchandising. Editorial Use Only. No Book Cover Usage. Mandatory Credit: Photo by Hbo/Darren Star Productions/Kobal/REX/Shutterstock (5886159t) James Remar, Kim Cattrall Sex and The City - 1998-2004 Hbo/Darren Star Productions USA Television

One of the enduring themes of “Sex and the City” was that the most compatible partners aren’t necessarily the folks who are the most like us. Richard was a perfect example of that, as the male equivalent of Samantha who ended up betraying her just as she opened herself up to being deeply hurt. Samantha gave him her heart — literally and figuratively, as some painfully on-the-nose voice-over reminded us — and he broke it. No wonder it took her a long time afterward to ever be in another serious relationship.

4. Jack Berger (Ron Livingston)

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Berger seemed like a perfect match for Carrie on the surface — attractive, funny, and a fellow writer. But that led to him being the cruelest sort of tease, thanks to his deeply rooted insecurities that took their relationship down a dark path; honestly, while he did break up with her on a Post-It, his real crime was seeming like a real possibility, a dream boyfriend who was eventually revealed to be a nightmare.

3. Aidan Shaw (John Corbett)

No Merchandising. Editorial Use Only. No Book Cover Usage.Mandatory Credit: Photo by Craig Blankenhorn/Hbo/Darren Star Prods./Kobal/REX/Shutterstock (5886159y)John CorbettSex and The City - 1998-2004Hbo/Darren Star ProductionsUSATelevision

Passive-aggressive to a painful degree, Aidan might have given off the air of being a nice guy, but really he was a Nice Guy™, the sort that tricks you into thinking he’s a great catch, but then reveals himself to be the worst. While Carrie was certainly no saint during their relationship, the ways in which he manipulated her left a sour taste in our mouths. Either break up with the girl or forgive her for her trespasses, but don’t avoid doing either. Aidan eventually became a husband and father, which, you know, good for him. But maybe even better for Carrie that she was spared that ultimate commitment with him.

2. Robert Leeds (Blair Underwood)

No Merchandising. Editorial Use Only. No Book Cover Usage. Mandatory Credit: Photo by Hbo/Darren Star Productions/Kobal/REX/Shutterstock (5886159bt) Blair Underwood, Cynthia Nixon Sex and The City - 1998-2004 Hbo/Darren Star Productions USA Television

Blair Underwood added some sizzle to Miranda’s life, but he handled their breakup in perhaps the pettiest and most disappointing fashion possible. Robert might have initially seemed like the perfect man, but the reality was that he ended up being a giant baby.

1. Aleksandr Petrovsky (Mikhail Baryshnikov)

No Merchandising. Editorial Use Only. No Book Cover Usage. Mandatory Credit: Photo by Hbo/Darren Star Productions/Kobal/REX/Shutterstock (5886159at) Sarah Jessica Parker, Mikhail Baryshnikov Sex and The City - 1998-2004 Hbo/Darren Star Productions USA Television

He. Hit. Carrie. Petrovsky, as played by Mikhail Baryshnikov, was an interesting late addition to the series, and he never sugar-coated what he was looking for in a relationship. But when he wasn’t being indifferent to Carrie he was being controlling, making every other boyfriend who’d come before him seem like an enviable choice. (Yes, even Aidan.)

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