Today marks 20 years since Sex and the City first hit our screens on HBO.
The tenured franchise’s 94 episode run had generations of women following the lives of Carrie, Samantha, Charlotte and Miranda and their loyal bonds of friendship are still firmly present in today’s pop culture.
We watched the four women navigate New York, trying to have it all while juggling both their careers and love lives. Of course some were more memorable than others – for both good and bad reasons, and we have ranked them all accordingly.
She might have been the serial monogamist in the group, but we’ll always remember Charlotte for dating her fair share of romantic duds before she finally found ‘the one’.
Ah, Ned, also known as the man who exploited his wife’s death to pick up women after he discovered that hanging out by her grave was a great way to pick up the ladies. Charlotte thought she was healing his wounds until she realised there was a bit of a line to his heart.
AKA the man who Charlotte convinced to get circumcision surgery, which led to him then dumping her because he wanted a chance to play the field with his penis' new sexual potential. Isn't that the way all good love stories end?
4. Trey MacDougal
Trey was one of Charlotte's 'great loves' and her first husband, but he was also a Mumma's boy who *ahem* had erection issues and said the word 'alrighty' more times than any grown man should. On paper Trey (played by Kyle MacLachlan of Twin Peaks fame) seemed like the perfect man to settle down with, but his story-line proved that looking good in public does not a happy marriage make.
3. Mr. Pussy
This man needs no more introduction than his name, pretty much. "Mr Pussy" enjoyed a whole lot of oral sex with women, which sounds great in theory, but things went a little awry when Charlotte tried to shape him into a serious boyfriend contender. Not really the kind of guy you want to bring home to Sunday lunch with the fam.
AKA the one who was okay with Charlotte not being the "up-the-butt girl". To be honest, Brian would be pretty much forgettable if it wasn't for the fact that his desire to try a spot of anal sex inspired the very best conversation that's ever taken place in the back of a taxi.
1. Harry Goldenblatt
Charlotte's forever husband... and the best boyfriend-turned-husband of them all. Harry and Charlotte's love story is one of the very best to came out of Sex and the City. At first, Charlotte was pretty embarrassed by Harry (played to perfection by Evan Handler) due to his appearance (yes, that makes us cringe even now) but he treated her so well that she fell head over heels for him. Watching them go through a difficult adoption process together only strengthened our undying love for Harry and Charlotte.
She's known as the most level-headed and feminist of the tribe but Miranda was not really given her dating dues in the relationship department. The strong-willed lawyer dated a long line of romantic B-s until Steve came along.
9. Thomas John Anderson
If you don't recognize Thomas John Anderson, one of Miranda's boyfriends from the early seasons, if doesn't mean your not a true fan. It could also be because he spent more time in the bathroom then he did with Miranda, thanks to the fact that the playwright felt the need to shower directly after sex.
AKA Carrie's friend whose parting words were "the fancy lawyer is breaking up with me". Every woman whose ex-boyfriend suddenly turned completely nasty after their break-up can relate to this episode. What a jerk.
Also known as the dirty-talk enthusiast who did not like being told that he liked 'a finger in the ass'.
Ted seemed like a bit of a contender for Miranda's heart, until he switched gyms after Miranda discovered his 'spanking porn' collection... this was a pre-50 Shades of Grey world, people. He was more interested in what was happening on the screen then he was in Miranda. His loss.
5. Tom: Season 5, Episode 4
Miranda met Tom just after she gave birth to her son Brady and at first he seemed like the perfect guy for her to move on with. They met at a Weight Watchers meeting and shared a love of doughnuts, all was going well until he didn't wipe his mouth after going down on Miranda. That's a bit of a deal-breaker.
4. Skipper Johnston - Season 1 (recurring)
AKA the lovable "seal pup" that was essentially the 20s-something version of Steve. The main flaw in this relationship was that Miranda was only into Skipper when he was in love with someone else...
AKA the guy that just couldn't make Miranda orgasm despite all of her guidance.
2. Dr Robert Leeds
Robert Leeds (played by famed TV actor Blair Underwood) was the witty New York Knicks sports medicine doctor who lived in Miranda's building. At first, he seemed too good to be true. He cooked, he was lovely to her son and respectful to her ex-boyfriend Steve. He even said "I love you" for the first time on a giant cookie. But despite all this, he just wasn't the right guy for her.
1. Steve Brady
No one else but Steve Brady (David Eigenberg), Miranda's longtime boyfriend turned husband, could claim the top spot. The fact that he cheated on her in the Sex and the City movie pretty much broke our hearts, but their reunion scene at the film's end kinda makes up for it.
Samantha Jones will forever be known as the sexually liberated publicist whose romantic conquests and pitfalls provided endless entertainment throughout the show's six season run. Here are some of her most memorable exploits.
AKA Samantha's recurring casual hook up who she inevitably developed feelings for.
8. Harvey Terkell
The man who Samantha very politically incorrectly dates because (face-palm) he had a servant... who turned out not to be a very nice woman. Not that we blame her for trying to get Sam out of the house, but that whole situation was pretty messed up.
7. Richard Wright
Richard Wright was the hotel-magnate who cheated on Samantha multiple times, with multiple women. Richard (played by James Remar) was one of the few men Samantha found herself wanting to be in a serious relationship with, yet he just couldn't get it together.
6. Chivon Williams
AKA the very un-PC story line which leads to Samantha telling his sister to get her "big Black ass" out of her face. Chivon seemed like a pretty great guy, until he chose his sister over Samantha.
5. Adam Ball
Adam will forever be known as the guy with the "funky tasting spunk" that no amount of pineapple juice, wheat-grass shots or ginger melon smoothies could cure. Adam was played by Bobby Cannavale, who then went on to play Will's husband on Will & Grace, so it's probably good that things didn't quite work out here.
4. Maria Diega Reyes
Maria was an artist and Samantha's girlfriend for a few episodes. Things were pretty hot and heavy there for a while between the two of them, but in the end the suffocating relationship proved to be a little too much for Samantha.
3. Bernie Turtletaub (the Turtle)
AKA Samantha's fixer-upper that didn't work out. His stint on the show was short, but very memorable.
James was the great guy with the unfortunately small penis. He was also the first guy we saw Samantha want to be in a long-term relationship with. But thanks to that one, er, small problem their love could not last.
1. Smith Jerrod
The beautiful male model with the heart of gold . Smith Jarrod (played by Jason Lewis) not only forgave Samantha for cheating on him he was also very respectful of her career and her smarts. He shaved his head in solidarity with Sam when she went through chemo and pretty much showed us what true love really looks like.
The one and only Carrie Bradshaw. She was the shoe-hoarding sex columnist who we'll forever treasure for her witty quips on love and her penchant for repeating the phrase "I couldn't help but wonder".
15. Keith Rodgers
Vince Vaughn was one of the famous faces who guest starred in the Sex and the City Los Angeles episodes. He played Keith, the guy who lied about being Matt Damon's publicist and was actually Carrie Fisher's personal assistant. Leading to a very awkward post-sex encounter with the Star Wars actress, who played herself.
14. Aleksander Petrovsky
Only famed ballet dancer Mikhail Baryshnikov could bring the suave and sexy Petrovsky to life. He was the man who whisked Carrie off to Paris and then slapped her across the face because she left him for Mr Big. Well, that's not exactly how it happened, but that's how we will choose to remember it.
13. Bill Kelly
Before John Slattery starred in the hit show Mad Men he played Bill Kelly on Sex and the City. Bill was the politician with a penchant for golden showers, yet he had the nerve to say Carrie was the unsavoury one...
Who could forget singer Jon Bon Jovi's guest appearance on Sex and the City? He played Seth, the guy Carrie met in the waiting room at her new psychiatrist's office. Their promising relationship came to an end when they realised that he loses interest in women after sleeping with them and Carrie realised that she always sleeps with the wrong men.
11. Wade Adams (Superboy)
AKA the younger guy who worked at a comic book store and lied to his mum about Carrie giving him marijuana.
10. Vaughn Wysel
Justin Theroux, the actor who might be familiar with as the former Mr Jennifer Aniston, played writer Vaughn. He was the one who had premature ejaculation issues but also had a really cool mum. So it almost evened out, but not quite.
9. Jack Berger
Berger (played by Ron Livingston) was the seemingly perfect guy who broke up with Carrie over a post-it note (and also resented Carrie for her success).
AKA the man who mistook Carrie for a high-class escort. At least he left her a whole load of cash...?
7. Kurt Harrington
AKA the casual hook up from the very first SATC episode.
Sean was the super cute bi-sexual who was too liberal for Carrie, despite her being a sex columnist. He was played by Eddie Cahill, who you might recognise from his role as Tag on Friends.
5. Joe Starr
AKA the New Yankee who made for a very effective rebound guy.
4. Ray King
Ray was the frenetic jazz musician who had the energy and attention span of a five-year-old boy. The sex was great but in the end his crazy was too much for Carrie to handle.
AKA the one that had so, so much potential but couldn't handle Carrie's crazy when he walked in on Carrie going through his stuff... fair.
2. Aiden Shaw
Aiden was the nice guy who Carrie came close to ending up with. The fact that he was played by lovable movie star John Corbett only made him all the more perfect. He wanted Carrie to be something she wasn't, but to a legion of fans he will always be the one who got away.
1. Mr 'John James Preston' Big
Mr Big. The only man who Carrie could have ended up with. Yes, he wasn't always the perfect guy, but he's Carrie's soulmate and you just can't argue with that.
Do you agree with our list? Tell us your favourite Sex and the City boyfriends in the comments.