Ranking The 107 Men Of “Sex And The City”

107. The Turtle (Tim Wheeler)

Paired with: Samantha
First appearance: Season 1, Episode 9, “The Turtle and the Hare”
The verdict: The Turtle was Samantha’s PR project. She was determined to turn one of New York’s richest but most repugnant bachelors into someone dateable. And it worked — so well, in fact, that he decided to move onto someone new.

106. Len Schneider (Robert Lupone)

Paired with: Samantha
First appearance: Season 3, Episode 8, “The Big Time”
The verdict: Unctuous Len was an act of desperation, someone Samantha turned to when she thought she was going through menopause. Once she got her period, she bailed.

105. William (Robert Montano)

Paired with: Samantha
First appearance: Season 2, Episode 4, “They Shoot Single People, Don’t They?”
The verdict: William was a total sleaze who promised to take Samantha on expensive vacations and turned out to be full of shit. But that should have been immediately apparent based on that smile alone.

104. Buster (James Urbaniak)

Paired with: Charlotte
First appearance: Season 2, Episode 12, “La Douleur Exquise!”
The verdict: Buster and Charlotte didn’t really date — he just let her try on some very expensive shoes for the chance to be close to her feet. It was a fine arrangement for a while, until it got too creepy.

103. Ed (Bill McHugh)

Paired with: Samantha
First appearance: Season 2, Episode 8, “The Man, The Myth, The Viagra”
The verdict: Ed was just too old for Samantha. Sure, he lavished her with gifts, and — thanks to his Viagra — was able to perform. But still.

102. Kevin (David Lansbury)

Paired with: Miranda
First appearance: Season 2, Episode 14, “The Awful Truth”
The verdict: Miranda thought Kevin was a little bossy and uptight, but his combativeness was part of being a high-powered attorney. It turned out he was really just an asshole and super unpleasant to be around.

101. Jim (Dominic Fumusa)

Paired with: Miranda
First appearance: Season 3, Episode 16, “Frenemies”
The verdict: Jim was actually Carrie’s ex, but he turned out to be another asshole Miranda dated as well. Even though Carrie warned Miranda about how awful Jim was, she didn’t see the extent of his dickishness until he started attacking Carrie in front of her.

100. Dominic (John Shea)

Paired with: Samantha
First appearance: Season 2, Episode 11, “Evolution”
The verdict: Samantha really wanted to teach Dominic a lesson for all the times he had screwed her over. Naturally, that backfired and he ended up screwing her over again. Best laid plans.

99. Jon (Kohl Sudduth)

Paired with: Samantha
First appearance: Season 1, Episode 4, “Valley of the Twenty-Something Guys”
The verdict: Samantha’s twentysomething wasn’t nearly as exciting as Carrie’s (who lands in a far better position on this list). To top it off, he was dumb enough to comment on her barely existent neck wrinkles, which made Samantha feel old. What a waste.

98. Kevin (David Lee Russek)

Paired with: Charlotte
First appearance: Season 1, Episode 11, “The Drought”
The verdict: Kevin seemed like a catch, but he couldn’t have sex. Like, at all. That’s because he was heavily medicated for anger management problems, so even if he went off the Prozac, he’d have some issues. Such a handsome guy, but a lose-lose situation.

97. Luke/Manhattan Guy (David Wike)

Paired with: Miranda
First appearance: Season 2, Episode 3, “The Freak Show”
The verdict: Things were doomed from the start with Luke, who quickly outed himself as Manhattan Guy and sneered at Miranda’s trip to Connecticut. Yes, Manhattan is a great place, but it’s not the only place on Earth.

96. Kurt Harrington (Bill Sage)

Paired with: Carrie
First appearance: Season 1, Episode 1, “Sex and the City”
The verdict: Kurt was the impetus for the whole “have sex like a man” philosophy that began the series, as Carrie decided to treat a past mistake like a piece of meat. So, yeah, Kurt’s one defining characteristic is that he’s a douche.

95. Mr. Cocky (John Enos)

Paired with: Samantha
First appearance: Season 2, Episode 18, “Ex and the City”
The verdict: Too big for Samantha, and that’s saying something. Mr. Cocky’s confidence was sort of charming, but since sex with him was literally impossible, it was all kind of lost on Sam.

94. Brad (Ross Gibby)

Paired with: Charlotte
First appearance: Season 3, Episode 5, “No Ifs, Ands, or Butts”
The verdict: Brad was a horrible kisser. Just the worst. And while he may have had good qualities outside of that, the impression he left was of someone who couldn’t figure out how to make out without licking Charlotte’s face. Sorry, Brad.

93. Siddhartha (Anthony DeSando)

Paired with: Samantha
First appearance: Season 1, Episode 11, “The Drought”
The verdict: That whole tantric celibacy thing would be fun for a while, but come on. Siddhartha absolutely refused to have sex with Samantha, even when he got an erection in her presence. Way too frustrating.

92. Greg (Anson Mount)

Paired with: Charlotte
First appearance: Season 2, Episode 17, “Twenty-Something Girls vs. Thirty-something Women”
The verdict: Greg was so young that Charlotte felt compelled to lie about her age. He was totally cute, but he also gave her crabs. So, probably not worth it.

91. Sam Jones (Jacob Pitts)

Paired with: Samantha
First appearance: Season 3, Episode 17, “What Goes Around Comes Around”
The verdict: Aside from the narcissistic thrill Samantha got from sleeping with someone also named Sam Jones — and taking his virginity! — Sam was just too young and needy to be taken seriously.

90. Harrison (Marc Kudisch)

Paired with: Samantha
First appearance: Season 2, Episode 3, “The Freak Show”
The verdict: Hey, to each his own. But Harrison’s instant transition from lawyer to BDSM freak was a little much for Samantha to take. Not to mention presumptuous!

89. Thomas John Anderson (John Benjamin Hickey)

Paired with: Miranda
First appearance: Season 1, Episode 12, “Oh Come All Ye Faithful”
The verdict: Talk about issues. Thomas John Anderson may have been a brilliant playwright, but his sexual hang-ups were too much to endure. When Miranda called him on his Catholic guilt, Thomas lost it and kicked her out.

88. Bram Walker (Kevin J. Flynn)

Paired with: Charlotte
First appearance: Season 2, Episode 16, “Was It Good for You?”
The verdict: Bram fell asleep during sex. Yeah, he had clocked in long hours at work, but regardless, that was totally unacceptable.

87. Shmuel (Glenn Fleshler)

Paired with: Charlotte
First appearance: Season 1, Episode 6, “Secret Sex”
The verdict: Apparently, Charlotte had a great time with this Hassidic folk artist, but they were from two different worlds, and neither would tell anyone about the other. If only he’d known Charlotte would eventually convert.

86. Dick Cranwell (Michael De Vries)

Paired with: Samantha
First appearance: Season 2, Episode 5, “Four Women and a Funeral”
The verdict: Samantha fooled around with this rich philanthropist in exchange for a donation — a noble cause, until his wife walked in and temporarily ruined Sam’s reputation.

85. Barkley (Gabriel Macht)

Paired with: Samantha
First appearance: Season 1, Episode 2, “Models and Mortals”
The verdict: Grossly obsessed with models and a total sleaze, Barkley gets points for being a sexy artist. He made Samantha feel lousy, however, when he refused to film her during sex.

84. Harvey Terkell (James McCauley)

Paired with: Samantha
First appearance: Season 2, Episode 10, “The Caste System”
The verdict: Ah, the thrills of sleeping with a man who has his own servant! Unfortunately, Harvey’s servant was very much in love with Harvey and treated Samantha like shit because of it. So much for being pampered.

83. Ned (Kurt Deutsch)

Paired with: Charlotte
First appearance: Season 2, Episode 5, “Four Women and a Funeral”
The verdict: Sweet, sensitive Ned was just the kind of open-hearted guy Charlotte was looking for. But the guy had baggage, namely a very recently deceased wife. And he was looking for comfort with a variety of women, not just Charlotte.

82. Doug (Jim Gaffigan)

Paired with: Miranda
First appearance: Season 4, Episode 3, “Defining Moments”
The verdict: Doug’s major flaw was that he insisted on no bathroom privacy. Not a big deal when he just wanted to pee next to Miranda, but as soon as he pooped in her presence, Doug was a goner.

81. Derek aka The Bone (Andrea Boccaletti)

Paired with: Carrie
First appearance: Season 1, Episode 2, “Models and Mortals”
The verdict: OK, so it turns out The Bone wasn’t really interested in boning Carrie — he just wanted to talk. And while that’s obviously disappointing, it’s nice to know there’s a thoughtful guy to go with that face.

80. Lew (Sam Seder)

Paired with: Miranda
First appearance: Season 3, Episode 14, “Sex and Another City”
The verdict: While he wasn’t the miserable guy Miranda remembered, Lew still had issues. For one, he was way too L.A. for Miranda to deal with. Also, he had a pretty serious eating disorder.

79. Lance Bloom (James Villemaire)

Paired with: Miranda
First appearance: Season 3, Episode 15, “Hot Child in the City”
The verdict: Love Miranda, love her age-inappropriate braces. Yes, she looked ridiculous with food stuck in them, but couldn’t Lance have given her a break? He seemed like a nice guy otherwise.

78. Jack (Will Arnett)

Paired with: Miranda
First appearance: Season 2, Episode 12, “La Douleur Exquise!”
The verdict: Sexy and adventurous, Jack would have been a great match for Miranda — he also loves historical biographies! — if not for his “getting caught in the act” fetish. Fine in a taxi, not so much in front of his parents.

77. Don (John Dossett)

Paired with: Samantha
First appearance: Season 2, Episode 13, “Games People Play”
The verdict: A good lay, to be sure, but Don could only get it up when his team won. That’s a bit too limiting for Samantha.

76. Howie Halberstein (Bryan Callen)

Paired with: Carrie
First appearance: Season 6, Episode 8, “The Catch”
The verdict: Harry’s best man was such a nice Jewish boy, he felt like a good fit for Carrie. He ended up being terrible in bed (and a little painful, leaving Carrie with “a sex sprain” on Charlotte’s wedding day), but hey, at least he looked good in a tux.

75. James (James Goodwin)

Paired with: Samantha
First appearance: Season 1, Episode 12, “Oh Come All Ye Faithful”
The verdict: James was the perfect man for Samantha — she was finally in love! But his penis just wasn’t big enough for her. While many women can overlook that sort of thing, Samantha is just too phallocentric to let it slide.

74. Keith Travers (Vince Vaughn)

Paired with: Carrie
First appearance: Season 3, Episode 14, “Sex and Another City”
The verdict: He was a handsome publicist who swept Carrie off her feet, but it turned out Kevin wasn’t being all that honest about his living or professional situation. (He was actually Carrie Fisher’s personal assistant, who tried to pass off his boss’ place as his own.) Still, this was Vince Vaughn in his prime. And everyone lies a little in L.A.

73. Ethan Watson (Rob Campbell)

Paired with: Miranda
First appearance: Season 2, Episode 6, “The Cheating Curve”
The verdict: Ethan needed to watch porn in order to have sex with Miranda. It’s not that unusual: Lots of men and women use porn to get in the mood. But every time? That’s a deal breaker.

72. Harris Bragen (Clark Gregg)

Paired with: Miranda
First appearance: Season 3, Episode 12, “Don’t Ask, Don’t Tell”
The verdict: He wasn’t really a doctor. But then, Miranda wasn’t really a stewardess. Since they were both in the wrong, it’s kind of a draw.

71. Joe (Nick Scotti)

Paired with: Samantha
First appearance: Season 5, Episode 4, “Cover Girl”
The verdict: Not exactly marriage material, but Joe the Worldwide Express delivery guy was at least hot. And his brief fling with Samantha felt like something straight out of a fantasy — or cheesy porn.

70. Alexander Lindley (Christopher Orr)

Paired with: Charlotte
First appearance: Season 3, Episode 6, “Are We Sluts?”
The verdict: Look, calling someone a “whore” or a “slut” during sex is fine as long as it’s consensual. But, for all of his charm, Alexander couldn’t stop shouting these words at Charlotte. And he didn’t remember doing it, so…issues.

69. Ted (David Aaron Baker)