'Sex and the City': Ranking Carrie Bradshaw's boyfriends

Sex and the City boyfriends — Ron Livingston as Jack Berger; Chris Noth as Mr. Big; John Corbett as Aidan Shaw. Photo:
HBO (3)

Pulling from her own escapades to fuel her sex column in the New York Observer, it's no wonder that Sex and the City's Carrie Bradshaw (Sarah Jessica Parker) had her fair share of steamy rendezvous and tug-of-war romances. Over the course of six seasons on HBO, the fashionista's boyfriends have run the gamut from successful to scrubby, from mature to inexperienced, and from great loves to crash-and-burn fiascos. But, naturally, certain beaus stole the hearts of fans more than others.

From easygoing furniture designer Aidan Shaw (John Corbett) to enigmatic playboy magnate Mr. Big (Chris Noth), see EW's definitive ranking of the men in Carrie's life, ahead.

23. Patrick Casey (Richard Joseph Paul)

It was the wrong time and the wrong place for Patrick Casey, who was played by Richard Joseph Paul in SATC's second season. The man recovering from his struggle with alcohol not only scarred Carrie with his cigarette butt, he embarrassed her in front of her whole block when he stripped in the street and repeatedly yelled about their tryst.

22. Howie Halberstein (Bryan Callen)

Howie Halberstein (Bryan Callen) may have looked like a promising weekend fling when he entered Carrie's life in the show's sixth season, but he quickly took a turn. A friend of Harry's (Evan Handler), Howie not only gave Carrie a night of terrible sex, but called her out in front of the entire wedding to top off the whole painful experience.

21. Kurt Harrington (Bill Sage)

Kurt Harrington (Bill Sage) was a bit of a scumbag, but he gets minor points for being the first man we saw Carrie with in the show's 1999 premiere episode. While he was hardly a stand-up gentleman, he gave Carrie what she needed: a lovely afternoon in bed and fodder for her column.

20. John McFadden (Dean Winters)

Dean Winters was hardly mayhem in Carrie Bradshaw's life as John McFadden, but he sure was mediocrity. He fell short when Carrie tried to turn him from f--- buddy into boyfriend, revealing that he brought little to the table besides calling cards and sex.

19. Jake (Bradley Cooper)

If he wasn't played by Bradley Cooper in his first-ever onscreen appearance, Jake would find himself even lower on the list. The playboy met Carrie after the publication of her humiliating New York Magazine cover, and not only took joy in her dubious newfound fame, but refused to let her out of his car when she asked to leave.

18. Gilles (Ed Fry)

Gilles (Ed Fry) had foreign sophistication, a dreamy accent, and a lavish hotel room, but he disappeared without leaving a number in SATC's first season. Carrie did get $1,000 and a date to remember out of the whole experience, and Gilles gains points for being a charming European architect and for buying Carrie's friends breakfast the next morning.

17. Wade (Cane Peterson)

Wade (Cane Peterson) was a bit of reckless fun for Carrie in Sex and the City's third season. The overgrown man-child still lived with his parents and blamed Carrie for the weed in his house when his mom showed up, but he about broke even as Carrie earned souvenirs of a custom-made Carrie comic book and a large stash of pot from their short-lived relationship.

16. Ray (Craig Bierko)

Played by Craig Bierko, Ray was a love-him-or-hate-him type fellow — Carrie loved him (at first) and Mr. Big (Chris Noth) hated him (always). The musician introduced Carrie to jazz, chic downtown bars, and his hip way of life, but also brought his hyperactivity and his lack of boyfriend material into the picture.

15. Keith Travers (Vince Vaughn)

When Carrie and the ladies made their way west to L.A., they met Keith Travers (Vince Vaughn), a man who "represented" Matt Damon. He and Carrie spent a couple of dreamy days partying in V.I.P. rooms and scouting out stunning California real estate, but with the surprise arrival of Carrie Fisher, it was soon revealed that he was nothing more than an assistant squatting in his boss' houses.

14. Seth (Jon Bon Jovi)

Jon Bon Jovi dropped in on SATC's second season as Seth, a man who saw the therapist Carrie spent a short time visiting. After flirting in the waiting room and playing a bit of Twister, he revealed his true colors when, in a shared moment of self-awareness, he told Carrie that he loses interest in women after sleeping with them...while in bed, post-coitus.

13. Jeremy (David Duchovny)

Carrie found herself falling for her high school boyfriend, Jeremy (David Duchovny), once more in SATC's sixth season. While he proved he wasn't a loser and they finally rounded the bases, Jeremy's place of residence in a Connecticut facility that provided mental health services was a bit of a roadblock in the former sweethearts' future.

12. Sam (Timothy Olyphant)

Twentysomething Sam (Timothy Olyphant) found his way into Carrie's circle in the show's first season. The young, hip suitor was cute, a good kisser, and got Carrie into all of the right clubs, but his lack of basic essentials like coffee filters or toilet paper was unacceptable.

11. Bill Kelley (John Slattery)

Bill Kelley was so, so close to being the best, but in the end, was one of the worst. Played by Mad Men's John Slattery, Bill had a strong start with his Staten Island meet-cute, jokes about half-points, and politician good looks, but when he shamed Carrie for her sex column after asking her to indulge in his own out-there fantasies, he was out the door.

10. Jeremiah (Sam Ball)

Jeremiah (Sam Ball) had potential: He was an acclaimed performance artist, he had cool tattoos, he still managed to pay the bills with his side hustle as a cater waiter, and he could do a mean rendition of Three Dog Night's "Joy to the World." He never got his full due, however, as Carrie soon found herself back in the arms of Big.

9. Sean (Eddie Cahill)

Eddie Cahill made his onscreen debut as Sex and the City's Sean. The bisexual twentysomething was honest, kind, and brought all of the right liquid courage to an ice skating rink, but his willingness to make out with both Alanis Morissette and Michael Medico was a little too much for Carrie.

8. Vaughn Wysel (Justin Theroux)

Justin Theroux (Jared/Vaughn Wysel) — HBO

Vaughn Wysel (Justin Theroux) had a lot going for him: He was a celebrated short story writer who was cute enough to earn a spread in GQ, he was charming and funny, and he had an amazing family led by matriarch Wallis Wysel (impeccably portrayed by Valerie Harper). The only thing not working with him was his body, which failed both Vaughn and Carrie in the bedroom. His unwillingness to face the issue at hand was simply the nail in the disappointing coffin.

7. Aleksandr Petrovsky (Mikhail Baryshnikov)

Played by famed dancer Mikhail Baryshnikov, Aleksandr Petrovsky came very close to being one of Carrie's great loves. The Russian artist literally swept her off her feet, but, when it came down to it, his work was his ultimate lov-ah and he was unwilling to have more children. We couldn't help but wonder, would that be enough for Carrie? No, the answer is no.

6. Dr. Bradley Meego (Patrick Breen)

Bradley Meego was actually a little bit of a dream date: He was a doctor with a house in the Hamptons, for crying out loud! If that wasn't enough, he was cute and kind and came to Carrie's rescue on one particularly crab-filled weekend. Carrie's loss, if you ask us.

5. Ben (Ian Kahn)

In a rare moment of romantic ineptitude, Carrie completely blew her chances with Ben (Ian Kahn). She was the "freak" in question in season 2's "The Freak Show," when she let her past tribulations get the best of her and went on a tear, snooping through all of Ben's stuff. While we didn't learn much about the political magazine editor, his thoughtful demeanor, Cub Scout values, and even temper in dealing with Carrie were enough to give him a second look.

4. Jack Berger (Ron Livingston)

When he was good, he was great; when he was bad, he was terrible. Jack Berger (Ron Livingston) had a lot in common with Carrie, from his profession as a writer to his flair for the dramatic. While his floppy hair, impressive intelligence, and boyish charm were all assets for the brooding creative, his ex-girlfriend baggage, jealous streak, and authorship of the world's most biting Post-it knock him down a few pegs.

3. Joe (Mark Devine)

No one was more criminally underrated than the new Yankee. Carrie snagged herself MLB player Joe (Mark Devine) in SATC's season 2 premiere, but, just like always, her roller-coaster relationship with Mr. Big got in the way. The athlete could've been perfect for Carrie with his dashing good looks, sense of humor, and coveted place in society, but after Carrie cried in his mouth, the end was near.

2. John James Preston, a.k.a. Mr. Big (Chris Noth)

2. Mr. Big aka John James Preston (Chris Noth) — Craig Blankenhorn/HBO

In the storied race of Carrie's great loves, there's only one winner, and it isn't Mr. Big. Finally revealed to be John James Preston (and played by Chris Noth), the businessman who was first introduced in the pilot won Carrie's heart in the end—but he isn't quite the best contender. Big was selfish, emotionally distant, and always looking for his next piece of arm candy...but then again, so was Carrie.

1. Aidan Shaw (John Corbett)

Aidan Shaw (John Corbett), was simply the better man. The gorgeous furniture designer (come on, he made his own furniture!) loved Carrie above all else, and he made her a better person through the relationship. The greatest man, he even had a dog, a country house, and more values and morals than Big could fit in his sprawling Manhattan apartment.