On Sex and the City: Valley of the Twenty-Something Guys

Every Outfit

This episode of Every Outfit revisits 'Sex and the City' Season 1, Episode 4, 'Valley of the Twenty-Something Guys,' focusing on pivotal moments in

Key takeaways

• The episode is considered a 'perfect' by Sarah Jessica Parker despite her lack of memory about the series.
• HBO's head at the time laughed when Darren Star pitched the anal sex storyline, signaling approval for bold content.

Main topics

• Big and Carrie's evolving relationship through repeated meet-cutes
• Charlotte's controversial conversation about anal sex with her boyfriend Brian

Notable quotes

'You got it all. You have Big and Carrie running into each other. You've got Charlotte in the anal sex conversation. To me, this is a perfect Sex and the City episode.' – Sarah Jessica Parker

Conclusion

This episode stands as a foundational moment in 'Sex and the City,' showcas

Transcript preview

Speaker 4 (0:00) $1000 on shoes? What's the matter Morty? Laurel? What's this thing? Great gown. Speaker 5 (0:15) Beautiful gown. Speaker 1 (0:17) Fashion has changed! Speaker 2 (0:23) Hi, I'm Lauren Garoni. And I'm Chelsea Fairless. And welcome back to the Every Outfit podcast. This is our monthly rewatch of a Sex and the City episode. Speaker 1 (0:33) We're talking about season one, episode four, Valley of the 20-something Guys. A.K.A. the episode Speaker 2 (0:39) where Timothy Olyphant guest stars and the infamous up-the-butt conversation happens. Can't wait to get into it. Absolutely. But before we do, whenever we do a rewatch episode, I always consult what I call the Bible, which is that pink book that they released before the series ended. It came Speaker 1 (1:00) out like after season four. If we ever have to testify in court, do you think they would let us swear on the Sex and the City like pink suede boxed set? I hope. I mean, we'll certainly try. But Speaker 2 (1:13) anyway, I always consult that book because they have anecdotes for every episode. And there were two very interesting ones for this episode. So Darren Starr gave a quote and Sarah Jessica Parker gave a quote. And Darren Starr's quote about this episode was he had to pitch this storyline to the head of HBO at the time. And he was like, I'm either getting kicked out of the office or they're going to laugh. And when he pitched this idea, he's like. look, Charlotte's boyfriend wants to have anal sex with her and she won't be Mrs. Up the Butt. And the head of HBO at the time, Chris Albrecht, laughed and Darren Star was like, all right, we're off to the races, I guess. And then Sarah Jessica Parker's quote about this episode, given what we know about Sarah Jessica Parker's memory of Sex and the City now, which is she has no recollection of making Sex and the City. what episodes, what happened in each episode. However, her quote in this book about this episode is that it's a perfect episode. She's like, you got it all. You have Big and Carrie running into each other. You've got Charlotte in the anal sex conversation. To me, this is a perfect Sex and the City episode. Speaker 1 (2:20) It's a great episode. I would argue that there are no truly bad Sex and the City episodes. There are some. less good episodes, I would say, in season one and in season five. But the quality was pretty consistent. Absolutely. And this episode is Speaker 2 (2:37) written by Michael Patrick King. It is directed by a woman named Alex McLean. This is her only episode of Sex and the City. I know her. for her feature film, Jesus's Son, which had Billy Crudup, which comes out a year after this episode. However, she is also known as the director of the Natalie Imbruglia Torn Speaker 1 (2:57) music video. See, that's my favorite genre of 90s music video, which is just like a woman in an apartment. Losing her mind. Yeah, like Lisa Loeb's Stay, I Missed You is another one of those like woman in an apartment music videos, but Natalie Imbruglia Torn, perfect. She tore with that video? Speaker 2 (3:17) She did. This director, Alison McLean, is a Canadian New Zealand director, and her first feature film, or the one that she became known for, is a movie called Crush that came out in 1992. Not to be confused with the 1993 Alicia Silverstone film called The Crush. Right. However, this movie seems very up our alley. It has Marsha Gay Harden as... A novelist, I believe. And then she's driving in a car with a literary critic and the car crashes and the literary critic has a traumatic brain injury. And then it seems that Marsha Gay Harden tries to seduce her 15-year-old daughter. Speaker 1 (3:57) Okay. I'm down for that. I did like Jesus' Son, as I remember. That was like a big awards season movie back when it came out. Speaker 2 (4:07) But as we've spoken about in the early seasons of Sex and the City. They did have a really healthy roster of female directors. Last episode, we talked about drama queens directed by Alison Anders. However, it seems that Alison McLean won and done. Speaker 1 (4:22) Well, she did what she needed to do. This episode is great. Speaker 2 (4:25) No notes. Well, maybe some notes. Some notes. So the episode begins with Carrie writing her article. Always a great way to start an episode. And then we see a montage of her and Big running into each other. Speaker 1 (4:38) Yes, and... Like all Sex and the City episodes, we get the Carrie voiceover. A certain man and a slightly less certain woman kept bumping into one another. They seemed to meet everywhere, on street corners, at parties. It was almost as if they were dating accidentally. And then after another chance meeting at a wealthy lawyer's new son's bris, they decided to be- They decided to pick a time to bump into each other on purpose. Sorry, just the detail of a mutual lawyer friend's son's bris. And this is the funniest moment of the montage because Carrie runs in in her cute little red Aliyah blazer at the exact moment that the baby is being circumcised. Speaker 2 (5:23) See, I remember this episode as the episode that Timothy Oliphant is in. I did not realize how much of a foundational text this episode is to Big and Carrie's relationship. This is Big's return. He's missing from the third episode. He's obviously in the pilot, as we know. He makes a brief appearance in the second episode, which we've done, Models and Mortals, where he bumps into Carrie at a bar and he's dating a model. And then she alludes to the fact that she also writes at a cafe. Never see this cafe after that episode. And he meets her there and kind of gives her the tidbit that like, yeah, beautiful women are great, but sometimes you just want to be with someone who laughs. Speaker 1 (6:01) Right. And Speaker 2 (6:02) here he is again. Because my memory is they meet and then there's the naked dress episode. They go on their first date. I didn't realize how many meet-cutes they have. Yeah. Speaker 1 (6:13) They have many in this montage. But before we move on, I do want to touch upon the Aliyah blazer because this is the first appearance of the Aliyah blazer. We also see it in season two in the Javier's funeral episode where she wears it with like a little pair of like black capris and it's much more like equestrian coated. Speaker 2 (6:36) Yeah, it's a really structured blazer. I wouldn't necessarily think it was Aliyah at first. And that's the fun of the early season of Sex and the City is because they didn't have as much of a budget. They do recycle outfits. Speaker 1 (6:49) Yeah, I also want to point out that she does carry the same handbag in both of these scenes with the same Aliyah jacket. It's this like red snake skin, like 80s looking clutch. I Speaker 2 (7:00) feel like Sarah Jessica Parker, when she came back for season two, was like, you know what, Pat? You know what was a good look from season one? The Aliyah jacket and that snakeskin handbag. We're Speaker 1 (7:09) doing it Speaker 2 (7:10) again. Speaker 1 (7:10) Before we move on to Speaker 2 (7:12) the next scene, I do just want to talk about this montage a little bit because the scene before the bris where they run into each other at a party, they don't exchange any words. It's almost this gravitational pull between Big and Carrie. And I was like, holy shit. I always forget how electric the chemistry between Sarah Jessica Parker and Chris Knoth is. It's insane. Till the moment he died. Speaker 1 (7:39) So the next scene is a nightlife scene. All the girls are trying to get into the hottest new restaurant in town. That, of course, Samantha is doing the PR for. This will become an Speaker 2 (7:52) oft story point that they will go back to time and time again throughout Sex and the City, which is we're all meeting at the new restaurant or club that Samantha is doing the PR for. Speaker 1 (8:01) Samantha's at the door. Miranda is there with Skipper, but she's lost Skipper. Or, yeah, where is Skipper? He Speaker 2 (8:09) eventually shows up. I mean, she wants to have no ownership of him when Charlotte asks where Speaker 1 (8:15) Skipper is. Totally. Well, Charlotte also is, like, a total bitch to Miranda. She says, I don't know how you can date that younger guy. They're so scattered and unfocused. And then Miranda says, we're not dating. It's a fuck thing. Yes. Which is, like, the way that the girls talk about sex in this episode is so... blunt and kind of crude and manlike. I do feel like in a sense it is an extension of the can women have sex like men conversation that we got into in the pilot. Speaker 2 (8:50) Well, yeah. And I think because this is the early part of the first season, a lot of the DNA of the dialogue is pulled directly from Candace's article. Those edges get a little more rounded as the seasons go on. Less sharp. Speaker 1 (9:04) Yeah, Miranda wasn't always quite this brash. Speaker 2 (9:07) Well, also, I think Charlotte is a little high and mighty because she herself has a new boyfriend, Brian. Speaker 1 (9:14) What's Brian's deal again? I already forgot, and I watched this episode yesterday. Speaker 2 (9:19) Who knows? All we know is that he's got Charlotte's big three, which are looks, manners, money, and he wants to buy a painting from her gallery. Not Speaker 1 (9:27) bad. But I'm curious, Lauren, what are your big three? Is this like a, is this commonly used terminology? Is this a thing or is this just like a Charlotte York thing? Speaker 2 (9:38) Probably a Charlotte York thing. Okay. If hers are looks, manners, money, I guess funny, not a sociopath and likes me. Speaker 1 (9:49) Okay. That's kind of dark, but I like it. Not a sociopath is like, so like a nice, caring person. Speaker 2 (9:57) Yeah. I mean, I guess kind is another way to put it, but certainly funny. I don't think I could ever be with someone who doesn't have a sense of humor, whether they have money or don't. That's not really been something that I care about. Totally. Speaker 2 (10:12) Dearest listener, you can't see me, but please know during the course of this podcast episode, I've been wearing my Warby Parker Butler glasses. They have a rounder eyeglass shape that I really think suits my oblong face. I have been wearing Warby Parker glasses for over a decade. When I first started wearing glasses as a teenager, it seemed that there were only two options. The un-stylish options at my eye doctor's office or designer specs at a fancy eyeglass place that was just always out of budget. But thankfully, Warby Parker came along. 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That's 20 % off any additional pairs when you purchase one pair at warbyparker.com Speaker 1 (11:44) slash outfit. Speaker 1 (11:47) I'm with you on that. I think my big three, sense of humor, definitely agree. I could not date someone that isn't funny. It's like a horrifying, terrible prospect. I think about it sometimes. Speaker 2 (11:59) And I asked Paul, like, what do couples do who don't have senses of humor? We see them at Speaker 1 (12:05) restaurants. They sit silently. It's horrifying. Well, Speaker 2 (12:09) the best thing that ever happened to those couples is the invention of cell phones. That's Speaker 1 (12:13) true. Speaker 2 (12:14) Because they're just, you're right, they're at restaurants, not talking, looking down at their phones. Okay, sense of humor. What are the other two? Speaker 1 (12:20) Instead of looks, I'm going to say chemistry because I think it's more important. It signals attraction, obviously, but I think that chemistry is kind of the most important thing, ultimately. And my last quality, I would say passion. Not necessarily passion for me, but like passion. passion for something. Like, do you have a hobby? Do you get excited by things? They don't necessarily have to be the same things that I care about, but there has to be something. I Speaker 2 (12:47) thought you would say a refined design sense because I don't think you could be with someone who doesn't have taste. Speaker 1 (12:54) That is true. That's my number four. That and I also don't think I could date someone that was super introverted. Like, I feel like I'm the introverted one, so I can't deal with dating someone else that's like that because it's too awkward, like if we have to go to parties or something. You Speaker 2 (13:12) consider yourself an introvert? Speaker 1 (13:13) Kind of. I Speaker 2 (13:14) consider myself an introverted extrovert. Like in social situations, I can be extroverted, but at home, quiet with my thoughts. Speaker 1 (13:23) Yeah, so many thoughts. Speaker 2 (13:25) Okay, back to Charlotte's boyfriend, because at first I'm like, Is that Chris Maloney? But it's not Chris Maloney. It is this journeyman actor named Josh Stamberg. And I looked him up because I was like, did he get recast as Samantha's wrestling boyfriend who does the baby talk? Which I think is in season two or three. It is not the same actor. But this is a Samantha boyfriend. Speaker 1 (13:52) Yeah, he Speaker 2 (13:53) does look like someone that Samantha Speaker 1 (13:54) would fuck for sure. Speaker 2 (13:56) Okay, so this is where Big and Carrie are supposed to go on there. I'm not going to say date because Big didn't say date. It's a drinks thing, which he is late for. Speaker 1 (14:06) So Carrie finds a phone, calls her voicemail. What a different time. Speaker 2 (14:12) This was a moment where I did feel young, where I'm like, did people do this? Speaker 1 (14:17) But of course. Of course people did that. I remember doing that occasionally when I was like. in elementary school, like at the mall or something, you know? But I never did that Speaker 2 (14:29) as an adult. Speaker 1 (14:30) We had cell phones. By Speaker 2 (14:31) then, yes, of course. So Big has presumably called Carrie's home phone, left a message to say that, well, she believes he's not coming to drinks. And she asked Miranda to listen to the message again, something I believe she does in season three. The more I watch these episodes, the more I'm like, wow, they really rhyme with each other. A lot of motifs come back. So Carrie's question to Miranda is, I can't tell if he's canceling as a friend or as a date. And Miranda listens to the voicemail that we don't hear and goes, I have no idea. And I came in first in my litigation class. Now, we know season one Carrie presented much more bumbling than, let's say, a season four Carrie. But girl, you are a love and relationship calmness in your 30s. What man wants to be your friend? Like, the question is, is he a situationship or does he want a relationship with me? Speaker 1 (15:29) Right. I Speaker 2 (15:29) don't think Big wants to be her friend. No. Speaker 1 (15:32) Does Big look like someone with woman friends? That's why it was so sus when he was flirting with Penelope Cruz in Sex and the City 2. Right, right, right. Because what's his objective? To be friends with this beautiful woman? I don't think so. Speaker 2 (15:46) Well, Carrie wonders this about Aiden when he won't fuck her. She is calling Charlotte being like, I think this guy is my friend. It's like, girl, no guy wants Speaker 1 (15:57) to be your friend. So true. Carrie should have like, figure that out by season two at the very least. Aye yi yi. Speaker 2 (16:05) So this is where Carrie and Miranda walk over to Samantha's booth where Samantha is sleeping with the chef, I guess, of this restaurant slash club. Yeah. They never clarify, but we don't care about John Noh, which is J-O-N, which is a big point of this episode. Carrie keeps referring to him as John Noh. Speaker 1 (16:27) Do you think at that point, Michael Patrick King knew that Mr. Big's name was actually John? Oh. So he had to have it like John with no H just to like switch things up. Speaker 2 (16:40) That's interesting. I wonder if it was not exactly a dig, but just like because JFK Jr. was probably looming so large in New York and culture that it's like it's not John as in John FK Jr. Right. John, no H. Jon doesn't really matter in this episode. Like Speaker 1 (16:58) a Speaker 2 (16:58) Jon Stewart. A Jon Stewart, exactly. But Jon doesn't matter in this episode. We just need Jon to make his crab strudel. What was it that Samantha was talking about? Yes. Well, Carrie says his crab strudel is so good he doesn't need the age. Speaker 1 (17:17) I don't know why the prospect of like crab strudel sounds like more of a threat than anything else. It does, because there's something about crab strudel, which feels Speaker 2 (17:27) like it would come with some kind of creamy sauce, maybe a hollandaise, that doesn't really mix with New York nightlife. Yeah, exactly. Speaker 1 (17:35) Seems a Speaker 2 (17:36) bit Speaker 1 (17:36) heavy. Speaker 2 (17:37) I'm really trying to get away from John, no age, to explain that the reason this character exists is more to introduce his friend, Sam, played by Timothy Oliphant. Right. Which... In my mind, kind of a step down for Timothy Olyphant because this is a year after he is Mickey the Killer Speaker 1 (17:55) in Scream 2. Do we think there was like maybe a bit of a delay with the release of the first season of Sex and the City, though? Speaker 2 (18:02) Possibly. They definitely shot in 1997. However, this episode comes out in June 1998. So while Timothy Olyphant was technically in his 20s when they shot this episode, he was 30 by the time this episode came out. Wow, you really are a Speaker 1 (18:17) human IMDb. I'm also a huge Timothy Olyphant fan. Yeah, because at this point, I knew him from Scream, obviously, and from his brief role as a douchey indie director in the First Wives Club, which would have been a couple years earlier. Well, Chelsea, I did look this up two years before. Speaker 2 (18:38) But he is playing the aforementioned 20-year-old guy. He has a tongue ring. Oh, my God. We'll get into that in a second. But I do love Michael Patrick King's dialogue with this, where he offers to get Miranda and Carrie martinis from the bar. And as he's walking away, Carrie goes, 20-something guys always know the important B people. Busboys, bouncers, plus they have cute butts. Speaker 1 (19:04) That's like such a Candace Bushnell thing. Like she loves like an alliteration situation. And Speaker 2 (19:10) I definitely believe that Candace made out with a 20-something year old with a tongue ring. I'm Speaker 1 (19:15) sure the title of this episode comes from her column. We should have looked that up before we sat down to record, but. We're not perfect, guys. No. So this is where Speaker 2 (19:24) Skipper shows up with two rum and Cokes because the bar had closed. And Miranda's like, great, I hate Speaker 1 (19:32) rum and I hate Coke. Well, to be fair, she wanted a martini. So that's like an insane thing to get someone that thought