Are You A Charlotte?

THE L WORD with Brian Van Holt (Sex and the City S2E10: “The Caste System”)

Podcast by iHeartPodcasts | Host: Kristin Davis | Guest: Brian Van Holt
Episode Date: August 18, 2025

Episode Overview

In this episode, Kristin Davis welcomes actor Brian Van Holt, who famously guest-starred as movie star “Wylie Ford” in the Sex and the City season 2 episode “The Caste System.” Together, they reminisce about the electric atmosphere of late-90s New York, the behind-the-scenes realities of shooting the show, and how Sex and the City became an unexpected cultural phenomenon. Their conversation blends hilarious on-set memories, real talk about sobriety in Hollywood, and reflections on careers, fame, and the power of discovering new talent.

Key Discussion Points & Insights

Revisiting the “Caste System” Episode & Life in ‘90s NYC

• Setting the Scene: Kristin and Brian paint a vivid picture of filming Sex and the City in 1999 New York, a time of energy, opportunity, and innocence before the explosion of social media (04:43–08:13).
  • Kristin Davis: “I remember that time as being that summer…It was kind of a glorious year.” (05:14)
  • Brian Van Holt: “To be in New York in the 90s was special in and of itself…I have one of my favorite moments of my—not just my career, but my life—was that time in New York.” (05:47–06:21)
• Old-School Acting Realities: Brian reveals he kept a Manhattan storage unit for years, filled with relics from his early career—most notably, pagers—highlighting a bygone era before cell phones dominated. (07:03–07:40)
  • Brian Van Holt: “When I went back to finally clean [the unit] out…two pagers, poems…I had written and taken back from my ex girlfriends and, like, weird stuff…notes, journals, and bad furniture.” (07:22–07:52)
• The Freedom of Pre-Internet Fame: Kristin and Brian reminisce about the liberty and anonymity actors enjoyed before ubiquitous smartphones and online scrutiny. (07:53–08:13)
  • Kristin: “So free, you could kind of do anything you wanted and no one knew.” (08:08)
  • Brian: “I miss those days.” (08:13)

Brian’s Casting & Reflecting on His Character, “Wylie Ford”

• Competitive Casting Process:
  • Brian describes how coveted Sex and the City guest roles were for actors and how he landed his spot on the show (08:35–10:12).
    • Brian: “To be on your show was such a big deal. Everybody wanted to be on it…It was a juggernaut. Cultural, like, pioneering…It was very competitive to be on your show and it was a big deal.” (08:35–09:16)
• Character Origins:
  • The character of Wylie Ford was loosely inspired by rumors around the infamous “Pussy Posse” of ‘90s New York (Leonardo DiCaprio & friends). (14:06–14:32)
    • Brian: “That character, Wiley Ford, was loosely based on the Posse shenanigans.” (14:22–14:31)
    • Kristin: “They probably kept that from me so that I wouldn’t judge it harshly.” (14:32)
• On Playing a “Douchebag Movie Star”:
  • Brian found creative catharsis playing someone so unlike himself and brought humor and self-awareness to the experience. (14:36–15:36)
    • Brian: “I get to channel my inner douchebag…and it was…very therapeutic.” (14:36–14:52)
    • Kristin: “I just thought you were perfectly cast because…you embody that kind of like, really relaxed confidence… almost like a Leonardo DiCaprio thing, but…in our minds, I think it was a George Clooney thing or a Brad Pitt thing.” (13:38–14:06)

Behind-the-Scenes Memories & KristIn’s Experience

• Positive On-Set Environment:
  • Kristin recalls the joy and comfort of having Brian on set, remarking how pleasant the experience was, versus how “jerky” his character was on screen. (12:11–16:38)
    • Kristin: “I thought you were so perfectly cast because you were having to play a movie star, which is a very hard thing to do.” (12:20)
    • Brian: “You were so…gracious and welcoming…That was, you know, super. Nervous to do this, were you?” (12:11)
    • Kristin: “No, you weren’t that way. In any way, shape or form. You were a joy, you know, and so I just remember the positives…” (15:49)
• Unexpected Realism:
  • Kristin is surprised by how much she’d forgotten about her own character’s storyline and Wylie’s behavior until she rewatched the episode. (13:21–13:38)
    • Kristin: “I hadn’t remembered the douchebag part. Really? Yeah…I totally forgot this entire scene. That entire scene at the restaurant washed from my brain.”

Discussing Sobriety and Hollywood Culture

• Navigating Sobriety in the ‘90s:
  • Kristin and Brian have a heartfelt discussion about the challenge of maintaining sobriety in an era (and industry) so closely tied to partying, sharing their own stories. (19:47–22:30)
    • Kristin: “I wasn’t drinking or doing drugs, so I wasn’t really cool, you know, ever…And I was like, I hope I can still succeed without doing all this stuff. And it was not clear in the 90s if you could.” (19:47–19:59)
    • Brian: “It would have been so difficult. It’s more acceptable now. You’re absolutely right. It would have been extremely difficult…probably drank too much and really had a good time in New York, you know.” (22:06–22:23)
  • Memorable Exchange:
    • Kristin: "I was open [about sobriety], but it seemed weird...I didn’t obviously know that the show was gonna go on so long and be this humongous thing..." (23:28–23:33)

The Impact of Sex and the City

• The Early Days of the Show:
  • Kristin reflects on the show’s uncertain start, not realizing from the inside how quickly it became a phenomenon and guest roles became highly sought-after. (31:59–33:49)
    • Kristin: “In my mind…it took till season three till we were even like on the map. So it’s super interesting for me to hear from people…everyone wanted to be on that show. It was the thing.” (31:59–32:45)
  • Enduring Legacy:
    • Brian shares how younger generations—including his own wife—still seek out Sex and the City, with DVDs turning into family heirlooms even in the streaming age. (35:04–35:52)
    • Brian: “Even…the kids, I say kids, and young adults today…are huge fans and so sweet.” (35:38–35:52)
    • Kristin on the show’s legacy: “I just don’t know how I lucked out so much.” (35:52)
    • Brian: “I lucked out to be…One episode—100% impactful episode. That one episode led to a lot of good things in my life.” (35:57–36:07)

Show Business Anecdotes and The Nature of Acting Careers

• Early Career Crossroads:
  • Brian recounts the whirlwind week when, while shooting Sex and the City, he was also auditioning for and landing other major roles—highlighting the unpredictability of acting work in New York. (47:23–48:41)
    • Brian: “Such a crazy week in my life…While we’re shooting our episode, Les Moonves…the head of CBS—I auditioned…You guys let me run uptown to meet with Les…And it got the gig.” (47:23–48:41)
• Lessons in Persistence:
  • Brian tells the story of fighting to get an audition for the David Milch show “Deadwood,” tying in how vital persistence and personal connections can be in landing “the right part.” (42:09–44:42)
    • Brian: “I will go there in person. I will break that door down. I’m doing this thing. I’m not taking no for an answer.” (44:28–44:42)
• Discovering and Nurturing Talent:
  • Kristin: “I love that part of our business—finding talent, being able to support talent, discover talent, show talent to the world, create a safe environment for them.” (45:51–46:27)
  • The two note that Sex and the City gave many “unknown” actors their first big break, listing examples like Timothy Olyphant and Dan Futterman. (42:21–45:47)

Notable Quotes & Memorable Moments

• On New York’s Magic:
  • Brian: “Being in your 20s and in the 90s in New York City…an incredible time to be alive.” (05:47)
• On Pre-Fame Innocence:
  • Kristin: “You don’t really know at the time how special it is.” (06:21)
• On Wiley’s Inspiration:
  • Brian: “That character, Wiley Ford, was loosely based on the…Pussy Posse shenanigans.” (14:22)
• On Guest-Starring on SATC:
  • Brian: “To be on your show was such a big deal. Everybody wanted to be on it…it was a big deal.” (08:35–09:16)
• On Playing Unlike Yourself:
  • Kristin: “I hadn’t remembered the douchebag part. Really?…I totally forgot this entire scene.” (13:21)
  • Brian: “I get to channel my inner douchebag…and it was…very therapeutic.” (14:36)
• On Sobriety Struggles in Hollywood:
  • Kristin: “I hope I can still succeed without doing all this stuff. And it was not clear in the 90s if you could.” (19:47)
  • Brian: “It’s more acceptable now…then, probably drank too much and really had a good time in New York.” (22:06)
• On Not Realizing the Show’s Importance:
  • Kristin: “When you’re in it, you don’t really know…for us, we were still—‘We gotta get out there and get all the press we can get.’” (32:45)
• On Cultural Impact:
  • Brian: “It helped shape our generation and culture, and still does…even today, my wife…her friends…still have the [DVD] collection in pink.” (35:08–35:36)
• On Early Career Chaos:
  • Brian: “I went from Wiley Ford to Eamon McBride, tested the thing, and hauled ass back down to Soho…” (48:21)

Timestamps for Key Segments

• Reminiscing about 1999 NYC: 04:43–08:13
• Landing the SATC Role: 08:35–10:12
• Origin of Wiley Ford & "Pussy Posse": 14:06–14:32
• Discussing Sobriety in Hollywood: 19:47–22:30
• On Sex and the City’s Impact: 31:59–35:52
• Career Crossroads Story: 47:23–48:41

Tone & Style

The conversation is nostalgic, candid, and frequently humorous—balancing the glamour and drama of show business with down-to-earth self-awareness. Kristin’s warmth and memory for people contrasts with Brian’s good-natured, often self-deprecating storytelling.

Final Thoughts

This episode offers listeners not just juicy behind-the-scenes Sex and the City stories, but a heartfelt look at what it meant to be young, ambitious, and (sometimes) overwhelmed inside one of TV’s most iconic phenomena. Brian and Kristin’s rapport makes for an enjoyable, honest ride through the “caste system”—of both fictional romance and real-life acting.