It’s a debate that will likely haunt our brunches for generations to come: Who was the biggest asshole on Sex and the City?
Many of us would likely choose one of the big names—perhaps Mr. Big, or Jack Berger, or Aleksandr Petrovsky. But what about those lower-tier boyfriends, whose names we don’t remember but whose infamy remains permanently seared into our memories? Yes, they were shorter-lived, but Sex and the City was absolutely lousy with porn addicts, manipulators, and Bad Bathroom Etiquette Guys, all of whom played a part in exposing the New York dating scene for the hell it is. Here, for your perusal, is a ranked list of Sex and the City’s irredeemable scoundrels, from least garbage (though still very much trash) to most despicable.
Alexander Lemley (Christopher Orr)
If dirty talk is your thing, go off. But this guy couldn’t stop yelling, “You fucking bitch, you fucking whore!” every time he came. Poor Charlotte couldn’t handle it, and frankly, neither could I.
Mike (Alex Draper)
In fairness, Charlotte was not on her best behavior in this relationship. Mike was uncircumcised when they met, and apparently, the sight of an unaltered penis was simply too much for Ms. York. She was elated when Mike said he’d get circumcised, but here’s the rub: Once he got cut, he dumped her to share his new, gorgeous penis with the world.
Wylie Ford (Brian Van Holt)
Actor Wylie Ford routinely did things like ambushing Charlotte with a mouthful of weed smoke at a party. He insisted on calling her “Charlene,” and in the end, his asshole coup de grâce was telling her (in front of all his friends) to “go to the ladies' room, stick your finger in your pussy, come back and let me smell it.”
… And that was after he mistook a fire extinguisher for a piece of art at her gallery.
Thomas John Anderson (John Benjamin Hickey)
As Miranda learned in Season 1’s “Oh Come All Ye Faithful,” nothing is less sexy than shame. Poor Tommy couldn’t have sex without immediately showering afterwards, and he went absolutely ballistic when Miranda called him on it. Ick—next!
Bill Kelley (Jon Slattery)
Mr. Slattery managed to squeeze every last drop out of his experience on SATC with not one but two episodes.
I know what you’re thinking, and I’m not here to kink shame: I have no problem with Carrie’s politician beau asking her for a golden shower. I do, however, have several problems with him breaking it off and calling her column “kind of seamy” while attributing that judgment to “some people connected with the campaign.”
You know those political types—always too cowardly to say what they mean.
Wade (Cane Peterson)
You know you’ve hit rock bottom when you’re dating a grown man who lives with his mother—especially when he smokes you out on the patio before claiming the ganja is yours when mommy gets home. Some “Power Lad.”
Doug (Jim Gaffigan)
This guy pooped in front of Miranda—pooped! No warning, no chance to flee, and no erasing this from my memory, ever. Send him to The Hague!!!
Ethan Watson (Rob Campbell)
Look, I get it; some men like to watch porn to get in the mood before sex. But this guy couldn’t have any sex at all without a skin flick in the background! When asked if he could cut the habit off, he offered a vom-worthy explanation: “I’ve only known you for a few weeks. But I’ve been involved with some of those women for years!”
Nope, nope, nope, nope, nope. NEXT!!!
Trey MacDougal (Kyle MacLachlan)
I’ll admit, I struggled to figure out where to place Trey. He wasn’t a bad guy, but he was an emotionally immature baby. His offenses were often unintentional. He never developed a sense of self away from his controlling mother, and as a result, he has absolutely no idea how to be a good partner.
Trey’s sexual impotence was a hurdle, but it’s practically beside the point compared to his childish inability to relate on an adult level. I mean, he gave Charlotte a fucking cardboard baby while they were struggling to conceive. Sorry, Trey—but at the end of the day, unintentionally garbage behavior still stinks.
Ned (Kurt Deutsch)
When she first met Ned at his wife’s graveside, Charlotte thought he seemed soulful and sweet—but as she soon learned, she was just one member of a small procession of women trying to bring him back to life with their love.
Arthur (Brad Beyer)
Arthur seemed like Charlotte’s knight in shining whatever when he punched a jerk at a bar for her, but as she soon realized, he mostly just liked to punch people in the face for no good reason. This is what we get for normalizing male aggression as a marker of virility!
“We” William (Robert Montano)
This guy really messed with Samantha, and that’s no easy feat. He drew her in with all these promises about what “we” would do together that summer in East Hampton—dancing on weekends, sailing, cooking big lobsters, walking on the beach… And then, he stood her up on a date for no reason whatsoever. A manipulative jerk like that can be nobody’s “lobster.”
Jim (Dominic Fumusa)
Carrie warned Miranda about this guy right from the start. Then again, Miranda was reeling after her date stood her up by dying—so her shaky judgment in that moment is perhaps understandable.
I will say this: At least Jim did Carrie the courtesy of being so awful at playing nice that he proved her right in one episode flat! By the end, he’d gone full 5-year-old on Miranda: “Ooh, the fancy lawyer lady is breaking up with me—like I give a shit.”
Harvey Terkell (James McCauley)
The man had a live-in “servant.” Need I say more?
Dominic (John Shea)
Samantha’s most infamous ex returns in Season 2. Tempted by the prospect of beating him to the punch this time, Samantha begins an affair with Dominic only to learn that nothing has changed; she still has a soft spot for him, and he’ll still screw her over for his younger paramour, Anka, the first chance he gets. Sam is no easy mark, but Dominic is a master manipulator.
John Preston (Chris Noth)
A controversial opinion: Anyone who says this guy is the worst man on Sex and the City has not thought about the question very hard. Is he shockingly small and petty for a guy whose nickname is literally “Mr. Big”? Absolutely. Does he mess with Carrie’s mind and heart every chance he gets? I don’t know—ask Aidan. And there’s his personality, which is also peak cringe: Sinatra and cigars and suits and record players and good God, we get it! There’s a reason it took an international move with a narcissistic monster and the specter of physical abuse to make Big and Carrie feel like endgame.
But is he really the worst? I don’t think so! At least he always had the courage to dump Carrie to her face. He cheated like Richard, but he wasn’t openly sexist like Richard. And most importantly, he never verbally abused or physically assaulted Carrie—the worst he did was get in a middle-aged mud wrestle with Aidan that one time at the cabin.
Jack Berger (Ron Livingston)
Look up “sad little punk” in the dictionary, and you’ll find this guy’s face right next to it. Jack Berger, rider of motorcycles and writer of humor books, also happens to be an insufferable, insecure coward. Make fun of men who give their dates carnations in Berger’s presence, and he’ll give you a proto-MRA speech about how ungrateful women can be—and God help you if you gently rib him about one idiosyncratic detail in his novel. You’ll never hear the end of it.
Berger can’t stand that his career flounders when Carrie’s flourishes, and so he turns her every kind gesture into an affront. When Carrie dares to buy him a Prada shirt, he repays her with a terrifying motorcycle ride—and ruins her ponytail right before a red carpet to boot. He breaks up with her just to crawl his way back in, and just when she thinks they’re ready to work things out, he absconds in the night leaving only a Post-It?! Absolutely not.
Richard Wright (James Remar)
This man is an emotional black hole where dreams go to die. He made Samantha cry when they first met by turning her down for a job because women are “too emotional,” and things did not get better from there. Samantha sees Richard as her male analogue, but as demonstrated by guys like William and Dominic, she also tends to underestimate how open-hearted she can become once her guard drops. She gives Richard a canvas that says “love,” and he returns the gesture by getting caught in flagrante delicto with another woman. Samantha might love the chase with Richard, but ultimately, it’s also what does her in.
Aleksandr Petrovsky (Mikhail Baryshnikov)
More than a decade after I first watched Sex and the City, one question continues to nag at me: Did Aleksandr Petrovsky mean to slap Carrie at their hotel in Paris, or was it, as he claimed, an accident? The show keeps it murky; when Carrie tells Big what happened, she uses passive voice: “I got slapped.”
Ultimately, I think I’ve decided it doesn’t matter; as his ex-wife hints to Carrie, Aleks is so self-centered that he spares no regard for his partners. He’s rude to Carrie’s friends from the jump, and then he whisks her off to Paris like an accessory, with no regard to how she might factor into his life once they arrive. After a few miserable weeks, he forces her to skip a book party—her first social gathering with French friends—only to abandon her when his art debut goes well. Aleksandr might make a mean pancake breakfast, but underneath all that old world charm, there’s nothing but soul-crushing narcissism.
Richard (Neal Jones)
Carrie’s friend Susan Sharon’s husband always terrified me. A businessman with a flickering hot temper, Richard spends all of his time on screen yelling. At the start of the series, Carrie urges Susan Sharon to do what makes her happy (aka leave her husband), but the show also isn’t particularly kind to Susan Sharon—who winds up flirting with a horrid friend of Big’s who asks her, “Do you ever stop talking?” This is enough to send Susan back to her horrible husband, and ultimately, the only “fix” for their relationship is a dog that her husband can yell at instead of her.
And Just Like That continues to treat Susan Sharon… strangely. We saw her in Episode 2 during Mr. Big’s funeral, where she told Carrie she’d forgiven her and was giving her a “Get Out of Jail Free” card over what happened in the past. “What happened between you two?” Miranda asks. “I have no idea,” Carrie replies. “I was hoping you knew.”
Justice for Susan Sharon—whose garbage husband was subtly but unquestionably the worst man in Sex and the City.
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