The Men of Samantha Jones: 8 Actors on Playing Infamous ‘Sex and the City’ Flings

“If you’re a successful saleswoman in this city, you have two choices: You can bang your head against the wall and try and find a relationship, or you can say screw it and just go out and have sex like a man.”

Those were Kim Cattrall’s first lines as Samantha Jones in Sex and the City, which premiered 20 years ago today. At the time, in 1998, it was revolutionary to see a woman onscreen be unapologetically single and sexually active—and not have it presented as a major character flaw. Actually, it’s still revolutionary.

And though the character would go on to have a handful of partners that went beyond one wild night—James (“and his teeny-tiny penis”), hotel-magnate Richard, fiery lesbian artist Maria, and sweet Smith—her every move remained groundbreaking throughout the franchise’s six seasons and two movie sequels. (Sadly, we’ll never know about the third.) After all, this is a woman over 40 choosing to be unmarried and childless, and it’s presented as a glamorous and enviable lifestyle. She makes her own money (and lots of it). She wears hats you can see from space and pulls it off. She beats cancer. And yes, she has sex “like a man.” Maybe even more than most men.

In fact, Sam’s no-fucks-given attitude is so necessary to the show’s DNA that it became a priority on set. “Every aspect of our scenes were essentially setups for Kim Cattrall to be Samantha—that campy, wildly humorous character,” Christopher Braden, who played Sam’s upstate lover Farmer Luke, tells Glamour.com. “It was a complete role reversal.”

So in celebration of Samantha Jones—and Cattrall’s portrayal, of course—we spoke to Braden and seven other actors about what it was like to play Samantha’s flings, work with Cattrall, and become a small but undeniably memorable part of TV history.

Farmer Luke

Played by Christopher Braden in season four, episode nine (“Sex and the Country”)

Samantha accompanies Carrie to Aidan’s cabin in Suffern, New York, where she spots Farmer Luke, a former NYC big shot who moved upstate, driving a tractor. “Who’s the farmer with the delts?” she asks. She heads to his barn, gets a lesson in milking cows, and rides Farmer Luke in his hayloft.

“I showed up to my audition at Silver Cup Studios as a rough-edged country gentleman, with old boots and a Ralph Lauren denim shirt on, and a navy blue handkerchief around my neck. I got the call that I booked it, [but] I had to be approved by Kim. So I go back to Silver Cup and I’m waiting in an office. The door opens and Kim sticks her head in; she looks at me, smiles, and says, ‘I’ll sleep with him.’ That’s the network version of what she actually said. And I was hired.

I didn’t really know the show, and I’m embarrassed to admit that, but I called my sister and said, ‘Listen, I just booked this job on a show called Sex and the City?’ And the phone drops.

We shot at a farm on the border of Queens and Long Island. It was an authentic, working farm, and I remember showing up and of course you go see hair and makeup first. Wardrobe had asked me to bring the oldest boots I had and they said, ‘OK, your boots are perfect. Throw on these overalls and lose the shirt.’ Ten minutes and I was ready to go.

So I meet the director, and the first thing he says is, ‘Chris, see that tractor over in that field? Guess what? You’ve gotta figure out how to drive it in an hour.’ [The man who ran the farm] was the real hero for the day because in one hour he taught me to drive that two-stick-shift tractor and how to milk a cow authentically. Milking that cow was my version of Stanislavski’s ‘Building a Character.’ That moment where Samantha gets hit in the face? It’d actually be impossible to do with the cow, so that was set-up with a production assistant and a baster.

The episode was one superlong day, close to 16 hours. We finished with the [sex scene] up in the hayloft. By that point, Kim was so generous to me—instead of disappearing to a trailer in between shots, she had two director’s chairs set up for the two of us, and she spoke to me, I’m not kidding, for 12 hours.

My mission in that scene was to be absolutely professional and respectful and let her take the lead. That’s exactly what happened. It was a closed set, because we didn’t have anything on except for modesty cloths. I asked her one thing before we started: Right before the cameras rolled, I looked up at her and said, ‘Kim, is it OK if I put my hands on your hips?’ She said, ‘Of course.’ And we were off to the races.

I ended up going to my agent’s apartment with my acting teacher [to watch the episode], and I felt like I was sitting there with my mother. That’s another thing: My mom called me afterward, and I said, ‘What’d you think?’ And she goes, ‘Oh, you were so good.’ I’m like, ‘Mom, that’s a really strange thing to say. I’m your son.’

I’m very discreet about what I’ve done in the past and I have a lot of humility, but I don’t think I’ve been on a single set where a PA doesn’t inevitably bring up the episode and then it spreads like wildfire. I have millennials walking up to me saying, ‘You’re Farmer Luke!’”

The NYU Wrestling Coach

Played by Peter Onorati in season four, episode eight (“My Motherboard, My Self”)

Samantha loses her orgasm after Miranda’s mom dies and calls up the NYU wrestling coach she’s been dating for a little help. No matter how many elaborate (and comical) sex positions they try, Samantha just can’t seem to climax.

“[Writer-producer] Michael Patrick King called me and said, ‘You wanna do this?’ We’re old friends, and he knew that I had wrestled in high school, and there was one time where we were doing an advanced improv workshop and I picked him up and lifted him over my head. He never forgot that. So I think I was the first choice.

I’ve only done a sex scene like that, where I was close to or completely naked, three times in my career. This was five of them. Of course all my buddies from back home and college go, [in a macho voice], ‘Hey, what’s that like?’ And I say, ‘Listen, pal, as an American male, you’re raised to want to be in that spot from the time you’re aware of your sexuality. Once you’re there, even with a minimal crew, and your ass is hanging out, it’s no fun.’ It’s a lot harder than my old buddies from the neighborhood think.

Kim, because she’s the one who did all these scenes, had this little cup made for her men, almost fashioned like an athletic supporter. There was this little cup that protected all the junk, so to speak, and clear plastic strings so that you couldn’t see them when someone was on top of her. There was one point where we were kind of going at it and the cup actually popped in and popped out. And Kim said, ‘What…’ And I said, ‘That wasn’t me. That was the cup.’ And she said, ‘I don’t mind it.’ I said, ‘Well, I hope you don’t, because we’ve got five more hours of this.’

This particular episode was about how her problems in life were giving her problems climaxing, so I said to the director [Michael Engler], ‘Listen, why do we have to suggest intercourse? Can’t we suggest something oral? I could lift her up, you could shoot right from behind my head. I can hold her up.’ Kim went, ‘I really love that idea.’ But the director didn’t get it; he wasn’t going there.

He had a sheet of Kama Sutra positions that he could envision camera angles with, and I then adapted them with some wrestling moves, like elevating a leg or blocking an arm.

I think we were getting ready to do the last scene and Kim and I are sitting there in our robes, and she goes, ‘I really want to thank you for doing this.’ I said, ‘Kim, it’s my birthday, and I can’t think of anything better than to bang you five times on my birthday.’ She goes, ‘It’s your birthday?’ I go, ‘Yes, but don’t tell anybody, I don’t wanna hear any shit about it.’ And so we shoot the last scene and I went back to my dressing room, put my clothes on, and I got to my car, but before I left, she had one of PAs go out and get me a Carvel birthday cake.

She was a sweetheart. When shows like that run forever and personalities get in the way and stuff, you hear things about people that may or may not be true, but there’s definitely always some sort of strife within a cast. My first job in television was the last season of Kate & Allie, and Susan Saint James and Jane Curtin were best friends, but by that time they were sort of in different camps about who was running the show, what was funny and what wasn’t, and so I got a great lesson coming into a show that had been on for a while, that even the best of friends can end up in different camps—maybe not enemies but different camps, for sure.

[Kim and I] sort of kept in touch. We’d taken a Polaroid [on set] and my hometown wrestling team [in Boonton, New Jersey] was doing a benefit, so I reached out to her and said, ‘Kim, I blew up that Polaroid of the two of us. Can you sign it? Because it would make a lot of money for my hometown wrestling team.’ She did, and then she sent me a copy of her book with an inscription too. She’s just really beautiful and a wonderful person to be around.”

Mr. Cocky

Played by John Enos III in season two, episode 18 (“Ex and the City”)

“You dated Mr. Big. I dated Mr. Too Big.” And so goes Samantha’s pun about the man she called Mr. Cocky. They met on Fifth Avenue and Samantha soon learned that his penis was so huge it was “like a wall of flesh” coming at her.

“I was in New York, walking down in the Village somewhere, and they had trucks set up for Sex and the City. I guess they were shooting, and I had some demo reels with me—they had the VHS ones back then—and I remember throwing [a copy] in one of production’s doors. I got a call a couple days later to go over to audition for the part with Michael Patrick King. I don’t know if it was because of the demo. They may have just thrown it away, it may have come through my agent—who knows?

I just remember auditioning and they were kind of laughing. I’m sure they saw quite a few people for that part, and it came down to, I don’t know…. His name’s Mr. Cocky and he was well endowed or whatever, but instead of him being cocky and being all flashy about it, I thought I would go the other way, where he was kind of embarrassed about it. He was insecure about it, which you wouldn’t think somebody would be, but it was a choice that I thought would be different than what everybody else would probably make. It took a lot for him to put it out there.

I haven’t seen the episode in ages, but every once in a while someone will post a clip on Facebook or Instagram. [People approach me about it] all the time. I just laugh and say, ‘Yup, sure, that was me.’ And not just girls—guys and girls. Everybody watches it. [They ask], ‘What are the girls like in real life? Are they all good friends?’

I remember it being fun. We played with [the sex scene] a bit. Samantha doing the breathing exercises, like she was doing Lamaze—we kinda tried one take like that, they liked it. Instead of her giving birth, she’s trying to fit me in. It was easygoing. It was just another job, a really quick, in-and-out shoot, so to speak.”

Chivon Williams

Played by Asio Highsmith in season three, episode five (“No Ifs, Ands or Butts”)

Samantha starts dating Chivon, a powerful black record executive, after meeting him at his sister Adina’s new fusion restaurant. The relationship is complicated by the fact that Adina doesn’t want her brother dating a white woman. The episode has been criticized for fetishizing black men and stereotyping black women.

“I remember coming into my [modeling] agency one day and the talent manager was like, ‘Asio, I have an audition for you for Sex and the City.’ I was pretty new to the game, so I was like, ‘Oh my God!’ I was extremely excited. I had my own opinions about the girls before I was even thinking about auditioning for the show—I was a very opinionated viewer, in a good way. I loved it.

I met [Kim] on set and she was in her room, and I kind of walked in and she looked at me and said, [in a Samantha Jones voice] ‘Chivon,’ and she gave me a big hug. I was in awe and happy to be there, and she just tried to make me comfortable: ‘Are you good?’ Our first scene was the [bedroom] scene. So I literally went to the studio, met her, went to my room, and they ushered me to the bed.

The next day it was my birthday, and we shot the restaurant scene. By that point we were pretty much talking all day, the whole cast and crew, whether it was on set, off set, and we were shooting that scene, and they paused the scene and all four girls went back and came out with a cake and candles and sang me happy birthday. It was magical.

Over the years, it’s been 18 years, the weight of being one or two African Americans on the show [grows] on you heavier. It was very intimidating, because all of New York is watching and there were only a few African Americans on the show, so I felt like, Yeah, this is big.

I think that, first and foremost, a brother out there working, at that time, was just a huge accomplishment. I was in awe of having that platform. But I tried not to overstate it because this is Sex and the City. They only showed like a quarter of what New York women were really doing. [The show] was like peeking your head through—it wasn’t sticking the whole body in. I think that’s what people were frustrated with, because they had to wrap up a big topic in 30 minutes. So with some of their episodes they could touch and go on light topics that were kind of like one-night-stand topics; when they came to our topic, it wasn’t a one-night-stand topic; it was a social topic. It was dealing with social, not issues, but a social reality. It was going to make some people happy and some people upset.

I think that the African American community and the black community worldwide really felt or understood the cultural presence of the show and the different male stereotypes or archetypes that were being presented in each episode. Don’t forget, it’s 2000, so Jay-Z was big, Puffy was big, the music industry was big, hip-hop moguls were huge. There was sort of a stereotype in that era—that was all that was available for us to do.

That era of hip-hop and black entrepreneurship, I totally connected with that. It’s nice to strive to get to a point where a character like Chivon is in life, where things are good, you can meet people and they know who you are. Knowing you’ve worked, you’ve gotten somewhere, and you’re able to enjoy the fruits. That’s kind of how Chivon was.

Like I said, I was working on the biggest show in the world, and I was one of two or three black guys that’s ever had a relationship with those girls on the show. I feel honored. I still get approached from it. I wish I could get a dollar for every time someone said, ‘Great episode!’”

Harvey Terkell

Played by James McCauley in season two, episode 10 (“The Caste System”)

Samantha is dating a real estate tycoon and isn’t comfortable with the fact that he has a “live-in servant,” Sum. Eventually, Sam finds out that Sum isn’t the subservient maid she (or Mr. Harvey) assumed.

“The sex scene was very interesting for me, only because I was naked and [Kim Cattrall] was not. [But] I was never shy about nudity. By then the show was a hit, so I was like, ‘Well, I’ll do it, whatever.’ There were a ton of crew people around, it was like, Yep, this is me. Welcome to me.

Those scenes under the sheets, there’s absolutely nothing sexual about them. It’s really positioning—‘you put your shoulder here’ and ‘give me a couple of thrusts’—and you’re done and everyone’s looking around waiting for the lunch break. ‘Give me two little pumps and you’re out,’ like a shot at Starbucks: ‘I’ll take a double pump of the macchiato.’

Kim was super nice. And, of course, [when we met] I had to mention Big Trouble in Little China,, because as a kid growing up I loved that movie. She had a ton of shit going on, because she was on a hit show, but she was extremely kind and giving and wonderful and caring.

I thought it was a great episode. It tackled the class system, which really, nobody talks about. I thought they tackled it with humor and a sense of importance that I didn’t necessarily see all the time on that show. The heavy lifting had to be done by the women, because I don’t think [Harvey] was too aware of what was going on with Sum. I can’t say he was dumb; he’s a big real estate broker and very wealthy and all that stuff, but he was more of a vehicle.

It’s a beloved show. If somebody’s asking for a résumé or if they mention the show I’ll go, ‘You know, I was on that.’ They go, ‘OH MY GOD.’ It’s that.”

Siddhartha

Played by Anthony DeSando in season one, episode 11 (“The Drought”)

Samantha lusts after her celibate yoga instructor, who tells her over green tea, “Imagine a three-year foreplay, where all that sexual energy is coursing through your body…. The only thing hotter than sex is not having sex.”

“When I went in for this part, I had been into yoga for years, and it was really catching on. I figured the character was probably, like, Sidney Hart—an ex-junkie from the East Village who saved himself with yoga. I went in and sat in full lotus and expounded on Mother Kundalini coiled at the base of the spine and all energy being sexual energy passing out to higher vortexes. I doubt another actor sat full lotus to audition.

So many men had to do embarrassing things on the show—I got off easy. I think the most embarrassing thing I had to do was wear a silver coat that [costume designer] Rebecca Weinberg threw on me at the last minute. My wife, who was my girlfriend at the time, had just come back from India, so I was wearing her clothes for the part, except for that silver coat and the orange outfit. All the white stuff was from India, they were her pajamas; she was a yoga instructor at the time.

[In the scene where Siddhartha has an erection] I was reading from a book called Sexual Energy by Elisabeth Haich. It was my own book that I had picked up because I had read a previous book of hers, and it just happened to be appropriate.

I’m actually a Thai yoga therapist in Pennsylvania [now], so I work at a couple of yoga centers, and no one ever recognizes me there. But [Siddhartha] was probably the most similar character to my personal self that I’ve ever played. I’m usually playing a fast-talking jerk of some kind—not what I aspire to. Siddhartha probably required the least amount of acting, but that didn’t limit how fun it was to be around all of those people whose work you really enjoy.

Kim Cattrall was and is an icon. She’s always been a sex symbol. She’s beautiful and funny and smart. She has tremendous versatility as an actor. It was really a thrill being in her proximity, let alone interacting with her. It wasn’t ‘She was the star and I was the guest’—she just was on the level, down-to-earth.”

Chip Kil-Kenney

Played by Victor Webster in season six, episode one (“To Market, To Market”)

When a stockbroker named Chip moves into Samantha’s building, she welcomes him with a basket of cheese, prosciutto, condoms, and handcuffs. In return, he gives her a post-oral insider-trading tip. He’s handcuffed to the bed with Samantha faux slapping him when the FBI busts in to make an arrest.

“I never used to watch the show. I was more into action, guns, car chases, and there’s a big absence of that on Sex and the City. [But] I had an inclination [of what the role might entail] when I auditioned. I had a lot of girlfriends that would have viewing parties at their houses; when I told them, they were freaking out. ‘You’re gonna be one of Samantha’s boy toys!’

I was a stockbroker for years, so I could understand the mentality of [my character]. The majority of the guys I worked with were pretty crazy, spending a lot of money every weekend in Vegas, drinking—so that’s how I looked at this guy. He was just a guy who loved to experience life and didn’t have a filter on his mouth when he, um, was doing certain things.

Luckily, we shot the stuff on the street first and didn’t have to go straight into the sexy stuff. [On my second day of shooting] I have a bunch of tattoos, so I had a bunch of makeup to do. Then I showed up in a robe and slippers, and there’s 150 people walking around. Of course, for me, it’s like, ‘Oh, wow, these are all people I’m meeting for the first time.’ It’s embarrassing—I’ve gotta do this simulated sex scene, and I literally have a sock on my junk. For them it’s like, ‘Oh, another half-naked guy on the show.’ It’s nothing for them. I remember it being very cold on set, which probably didn’t help the situation.

[For my final scene] I was really handcuffed to the bed, with actual handcuffs. When you’re shooting scenes like this it’s 100 percent choreographed. Everybody has to position themselves so as not to cast a shadow on somebody else. So if it’s six inches too far this way, it’s too much—I’m now putting a shadow on her. If you move four inches forward, your shoulder blocks my face.

It’s always interesting when you meet somebody on the street and they’re like, ‘Oh! I know you from Sex and the City.’ And I’m like, ‘Well, you know a lot of me then.’ People always ask, ‘How was it working with Kim Cattrall? Is she as wild and crazy in real life as she is on TV?’ I can only answer one of those: She’s so easy to work with, really sweet, just a professional.”

Tom Reymi

Played by Sam Robards in season three, episode 11 (“Running With Scissors”)

Samantha finally meets “Manhattan legend” Tom Reymi—a.k.a. “the male Samantha”—but he refuses to have sex with her until she gets tested for HIV. After her test comes back negative, they have sex in a swing until it falls from the ceiling.

“I’m pretty sure the swing scene was shot last. They showed it to us and we sat in it clothed and rehearsed how they wanted it to look, then we got undressed and put on our little triangles. We’re just wearing little triangular, flesh-colored pieces over our privates, Kim is right on top of me, and we’re swinging away. It’s like that [saying], I’m sorry if I get excited, and I’m sorry if I don’t—you never know if it’s going to happen, and with Kim pretty much naked…we’re bumping up against each other, and I’m thinking about potatoes. It can get, you know, a little embarrassing.

We shot [the scene] with a swing that was locked in there first. Then they fixed it somehow so they could cut it loose when they needed to, and, basically, there was a pad underneath us. The hardest thing for me was I needed to hold on to this bar that was above us and they said, ‘Just make sure when you fall, the bar doesn’t hit Kim on the head.’ When they cut it loose and we hit the pad, of course I was trying to hold it as hard as I could, but gravity is much stronger than I am so it sort of bopped her on the head. Nothing serious. And then I was like, ‘Great! Thanks for everything. Bye!’

I’ve had some people [approach me] like, ‘Oh my God, you’re the guy on the swing’—just randomly. And you’re like, ‘What?’ Mostly people are just like, ‘You went to school with my sister,’ and I’m like, ‘Yes, how is she?’ People think they know you from somewhere; they’re just not sure where.

One of the great things about [acting] is you get to do things that you wouldn’t maybe normally do, but you can do it and have fun with it. No harm, no foul. Believe me, I was so happy to get the gig. Even pretend sex is great.”

These interviews have been edited and condensed. Image credits: Getty Images, HBO, Jose Marquez Photography, courtesy of Christopher Braden, Lynn Shupp