Sex and the City turns 25: A conversation with Skipper, Carrie's nice-guy pal from season 1

Sex and the City turns 25: A conversation with Skipper, Carrie's nice-guy pal from season 1

When Sex and the City debuted on HBO 25 years ago today, a few things about the now-classic comedy were different. There were those man-on-the-street interviews with random people opining on the topic du jour ("Has monogamy become too much to expect?"). There was the way Carrie (Sarah Jessica Parker) had a habit of breaking the fourth wall and addressing the camera directly.

Sex and the City grab
Sex and the City grab

HBO Sarah Jessica Parker on 'Sex and the City'

And then there was Skipper. Introduced about six minutes into the pilot, Skipper Johnston — played by Ben Weber — was Carrie's "hopeless romantic," website designer pal who fell hard for Miranda (Cynthia Nixon) in the series premiere. The two began dating, and Skipper maintained a regular presence throughout season 1, alongside the two other recurring guest stars, Willie Garson (as Carrie's gay BFF Stanford) and Chris Noth (as her elusive love interest, Mr. Big).

Whether hanging out with Carrie alone or courting the skeptical Miranda, Skipper was one of the OG SATC players — until he wasn't. After getting back together with Miranda in the season 1 finale "Oh Come All Ye Faithfull," Skipper all but disappeared from the Sex and the City-scape. Other than a brief appearance in "The F--k Buddy" (season 2, episode 14), Skipper went the way of those man-on-the-street interviews and to-camera interludes, which were ultimately dropped from the series.

Thanks to Weber's sweet and funny performance, Skipper holds a place in the hearts of die-hard SATC fans to this day. In honor of the show's 25th anniversary, EW reached out to Weber to celebrate Sex's brief but memorable Skipper Era. And the actor — who went on to star in the groundbreaking gay rom-com The Broken Hearts Club and can next be heard in the historical fiction podcast Going Reno — was happy to share some memories from his time in Carrie Bradshaw's inner circle.

ENTERTAINMENT WEEKLY: Before SATC, you had appeared in two big movies — Twister and The Mirror Has Two Faces. Had you done any TV?

BEN WEBER: No, and it was all new to me. I had been in a movie, but I was an extra, pretty much in Twister. I had a tiny part in that, and the same with Mirror Has Two Faces. I was learning how to act on those jobs. And the medium of [cable] television was still being sort of invented also. HBO hadn't done [much] original content before, so it all felt so new and exciting.

What do you remember about your audition?

I don't remember it being that big of a deal. It felt kind of lower stakes — who is this, HBO? It didn't feel like that big of a deal. Obviously, what was being discussed in the scripts, that was a revelation and that was exciting. But I don't even know if I was really that nervous for the first meeting that I went in on. It was just probably at [casting director] Billy Hopkins' office and it was probably like one or two other people there. At the time, the goal was to get on some big network show or something. HBO wasn't even on the menu for my young mind.

Ben Weber (as Skipper) from Sex and the City season 1 (Screengrab)
Ben Weber (as Skipper) from Sex and the City season 1 (Screengrab)

HBO Sarah Jessica Parker and Ben Weber on 'Sex and the City'

When you got the part, what was your understanding of how often you'd be on?

I was totally winging it. I had not gone to New York to be on Broadway. I really had gone to New York because I was a funny guy and I wanted to do comedy. My vision was, I wanted to be like a writer on SNL or something. It was never even in the plan to be an actor. But then this agent saw me performing in a club and introduced me to Rhonda Price, and she believed in me and started sending me out. She had a bunch of really big clients, it was way outta my league. [Laughs] But I got the Sex and the City meeting, and I got the job. It was the greatest New York job to get.

I remember hearing that I was going to do the first season, and I just was like, "Great!" It wasn't until we did our first read through that I was like, "Oh my God, like, this is nuts!" Like, what's being talked about even in the first episode and the way that it's being approached, and the people that were involved. I had my first scene with Sarah Jessica Parker, and she gave me this incredible boost of energy, and it just took off from there.

Ben Weber (as Skipper) from Sex and the City season 1 (Screengrab)
Ben Weber (as Skipper) from Sex and the City season 1 (Screengrab)

HBO Cynthia Nixon and Ben Weber on 'Sex and the City'

Skipper and Miranda go on a date in the pilot and then have sex in episode 2. Did you know much about their story arc when you joined the show?

I would get the script and I'd read it, and it was just sort of a week by week thing… I think as we started to understand what our roles were, I got to be a little bit more comfortable. It was great to be starring opposite Cynthia Nixon, but I definitely was a little intimidated by her, especially when we started to have sex scenes and stuff. I was trying to put on a brave face, but when you get to your dressing room and there's a nudity waiver and there no wardrobe, I was sort of confused by it. This was, like, the first or second episode. I was like, "Wait a minute, how did I already get to this point in my New York acting career?" [Laughs]

But it, it was great. And I powered through, and I think everybody was kind of thrown into the deep end a little bit. But how the show was talking about sex was so funny and so fresh and so forward-thinking. I was just like, "Whatever, I don't care if I'm naked the entire season."

Do you have a favorite Skipper moment?

It was funny because I didn't have HBO at the time, so we had to go over to my grandparents' house to watch a lot of the episodes. They are European and they were slightly more forward in their attitudes about sex on television. But it was still the funniest way to have to watch it. And at that time, I had just met my wife, we had just started dating. Her folks are from eastern Pennsylvania and super conservative. She was like, "Oh, I'm dating an actor, and he's on this show with 'sex' in the title.'" They were like, "Oh, okay honey. I hope you're making good choices."

At any point during production, did you have conversations with anyone about whether Skipper would return for season 2?

I didn't, really. It was all just gravy to me. I was so young, too, and I had no expectations about the show. I was just really happy for anything. And it made sense that they went where they went with the show, and it would've been great to have gone along with it. But I was 25, 26 or something. I was standing on 57th Street after the show premiered, and some guy in a three-piece business suit was like, "You were on TV last night!" [Laughs] I'd been acting for five minutes, and to have this made-it-in-New York moment — I would've been happy to have been on that show for five minutes. The fact that I got to be a part of the show, I'm going to remember that for the rest of my life.

Skipper returns in the season 1 finale and he and Miranda get back together — but that's the last time we see them together! When you got the finale script, were you thinking it meant that you'd return as a regular guest star for season 2?

Yeah, I did. It was a little bit sad, [because] it did seem like there was going to be more. But [Candace Bushnell's] book was very much like, every week she was dating somebody new, and the show became more like that. I understand where they went with the show, but yeah, it was sad.

Ben Weber (as Skipper) from Sex and the City season 1 (Screengrab)
Ben Weber (as Skipper) from Sex and the City season 1 (Screengrab)

HBO Cynthia Nixon and Ben Weber in the 'Sex and the City' season 1 finale

How did you find out that Skipper wasn't returning?

I don't remember. I think I did go to the [season 2] premiere or something. I was auditioning for other things. Every actor at that time was like, "The real money is on the network shows!" I would tell somebody I was on this HBO thing, and it was just like, "What?"

Because Sex and the City became such a phenomenon, did that give you any kind of advantage as you moved forward looking for other parts?

Yeah, I have definitely gotten work because of it. And I have a great agent, Jodie Bowman, because of it. She's a Sex and the City superfan. I'm very appreciative and grateful.

After SATC, you appeared on a lot of notable TV shows, including The West Wing, ER, Everwood, and The Secret Life of the American Teenager. Did decide to remain focused on TV because of your experience doing SATC?

Yeah. It was nice to do established shows with established casts and stuff, but it was also great to be in something that was debuting and was just totally new. I don't think I'll ever get a chance to do something like that again. I kind of had that experience a little bit later in the commercial world when I did the original Geico Caveman commercial campaign. That was sort of a similar experience in that we were not really expecting it to break out. [Laughs]

You've done a lot of popular commercials since then — do people recognize you most from your commercial work, Sex and the City, or something else?

I get Skipper a lot and then I also get Broken Hearts Club a lot. I was at a farmer's market with one of my kids recently and somebody came up to me and said, "You are great in The Broken Hearts Club!" I was trying not to freak out, but it's so hard sometimes with your teenage kids to get them to appreciate the stuff that you've done. So, to have somebody recognize me and make a big deal about that, that made me feel great.

Have either of your teenage sons seen Sex and the City?

I don't think so. That would be so funny. I think the word they would use is "cringey."

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