Amy Heckerling’s 1995 gem Clueless blew up the teen comedy genre and its epicenter was its iconic party scene, in which socially gifted Cher (Alicia Silverstone) unsuccessfully plays matchmaker for her naive new friend Tai (Brittany Murphy) and their “snob and a half” classmate Elton (Jeremy Sisto). The scene has it all: the socially gifted Cher uttering the classic putdown, “Do you prefer ‘fashion victim,’ or just ‘ensembly challenged’?”; Murphy singing Coolio’s “Rollin’ With My Homies”; Murray (Donald Faison) “keeping it real” by getting his head shaved; the suck and blow game. Vulture has been memorializing iconic slices of pop-culture all week through our series of micro oral histories, and now it looks like we’re going to have to make a cameo at the Val party. Read on as Heckerling, Silverstone, Faison, Sisto, Breckin Meyer, and, yes, Coolio, break it all down, but remember to do a lap before you commit to a location.

Amy Heckerling (writer-director): Like Cher, I’m not real familiar with the Valley. But when I was writing it, I was just thinking, What would be really foreign and far away to her? Based on Jane Austen, I needed a place that [Cher] didn’t want to go to because she didn’t think it was, you know, up to the standards of places she could go. [That’s why the party] was in the Valley.

Breckin Meyer (Travis Birkenstock): Party scenes are always weird because you have the fake smoke being blown in, you have a ton of background people smoking fake cigarettes, which, oddly enough, smell weirder than real cigarettes. I remember that distinctly, having a headache from all the smoke/fake smoke.

Alicia Silverstone (Cher Horowitz): Any moment that I got to be Cher was just wonderful, so I was in my Cher element [while shooting the scene]. But I don’t even think Cher had fun at that party. I’m sure that she was not in the party vibe. She was just like, It’s all business: You go in there, you see what’s going on, and if it’s not working, you’ve got to go. It was like a business transaction or something.

Donald Faison (Murray Duvall): It took a long time to shoot that scene. I remember falling asleep, and being woken up by Tara Reid, who was not in the movie but just came by the set to hang out. Which was really odd. I went to high school with Tara Reid so when she woke me up, it was kinda like, “Yo, what are you doing here?”

Heckerling: A friend of mine in her twenties wanted to have a party but she didn’t really have a place to have it. I said, “Oh, you can do it at my house.” Essentially I was just hanging around, watching movies, doing whatever I’m doing, but there’s a party going on at my house. And [suck and blow] was one of the things I observed. They were playing that game. I said, Huh, what’s that? I’ll use that.

Silverstone: I love the suck and blow thing — am I saying that right? I love that, when Jeremy gets in there and tries to snag a kiss. I just love it. [laughs] I definitely hadn’t heard of [the game before the movie]. I’ve never heard of it again since then.

Meyer: If Travis was any good at trying to woo Tai, he would have realized he should have dropped the napkin.

Heckerling: I wanted to put Tai in the position of needing to be rescued and make it as though Elton had helped, when, in reality, he had nothing to do with anything. So I had the idea of [Tai] getting hit in the head with a clog when people are doing sort of a move together and a clog comes flying across the room. Well, we did the take a few times with a clog flying off and we also had a foam rubber clog that we made, and we hit Brittany in the head a few times with it. But when I cut it all together, the motion of the clog coming off the girl’s foot and flying into Tai — it was all too slow. It happened so fast that you didn’t really see it. So we had to animate it slower and have a fake clog. I think it was drawn in. We had to create a special effect, essentially on regular film that was not shot for special effects, of a slower, darker, more noticeable clog going from the girl’s foot and hitting Brittany.

Meyer: That [moment] is the only time Brittany and I came close to kissing. Because we never actually kissed, even though we played boyfriend-and-girlfriend probably four or five times. Even in Clueless. At the end of the movie I’m supposed to give her a kiss at the wedding scene, but because Brittany was always so close to me and like a sister, you’ll see in the movie that I just kiss her on the top of the head.

Silverstone: I love when Brittany Murphy does her little “rolling with the homies” [hand gesture]. It’s so sweet. She was so special for that role and just adorable and lovely and brilliant. It’s so weird to think she’s not around anymore. It seems very abstract. [Murphy died in 2009.]

Meyer: She was amazing. She was so sweet and so much fun, especially that character in Clueless. It continues to suck that she’s not here.

Faison: She had that spark, you know what I mean? I honestly believe that’s why everybody remembers the song because one, she’s so cute when she sings it. Two, you didn’t expect that voice to come out of that girl when she sang. So when she does that line, it’s like, “Holy cow, she can sing?”

Coolio (co-writer, performer “Rollin’ With My Homies”): I was just asked if I had a song that could possibly fit in the movie, and it just so happened that I did.

Heckerling: I liked Coolio for that part of the movie because I wanted something that involved hand movements or movements that everybody would be doing together that could mess up Tai. The song that I was originally thinking about when I was writing it was “Slide, slide, slippety slide” [from Coolio’s “Fantastic Voyage”].

Coolio: [The lyrics for] “Rollin’ With My Homies,” those were the original lyrics for “Fantastic Voyage.” That’s what I was going to put out for “Fantastic Voyage” in the beginning but a guy who worked for Tommy Boy [Records] heard the [original version of] “Fantastic Voyage” and told me, “If you change your lyrics a little bit and make it more universal, I think this song could do good.” So I took off the original lyrics and re-wrote the whole song. And the rest is history.

Jeremy Sisto (Elton Tiscia): It doesn’t bother me anymore [when fans sing it to me]. It did for years, because I wasn’t sure if I was going to keep working as an actor. If I hadn’t kept working then it would have been a constant reminder of my failure [laughs]. But now I’m fine with it.

Meyer: To this day, I have no idea what people are talking about when they come up and they just say “Rolling With My Homies.” Every time someone comes up, it takes me a second to realize what they’re talking about. They do the hand gesture, but that signals rough waters to me.

Sisto: I think I made that [dance] up. I don’t think we had a choreographer. I did my go-to, funny, whatever-I-thought-was-a-douche-y dance at the time. I remember being kind of uncomfortable about it because I was awkward about dancing. I probably still am. It’s uncomfortable to dance in front of the camera unless you’re a trained dancer.

Faison: When it was finally time for me to shave my head, they didn’t want me to shave my whole head. They just wanted to shave the top of it so that when I have on hats throughout the other scenes, I’d still have hair on the side. And I remember them shaving my head and me looking like George Jefferson by the end of the night.

Meyer: On-screen, Donald had all these cool hats and lids and all these great Kangol, Sam Jackson-type hats. And in reality, every time you knocked his hat off, he was George Jefferson at 20 years old. So it was fantastic for me and [Paul] Rudd to just know that any time we wanted to, we could see what Donald would look like as George Jefferson.

Silverstone: Oh, I don’t remember that. [Laughs] Oh, I see, because of the sideburn kind of thing, right? I can see that now that you said that.

Faison: Look, I’m a light-skinned black guy who kinda resembles Sherman Hemsley. So if you shave my head to look like that, guess what? I’m going to look like that.

Heckerling: It’s hard to remember, [but] I think “I’m keeping it real” was in the script. And “It’s the bomb.” When [Murray] says, “Look how good he looks,” and his friend says, “As will you,” I think that was them [improvising].

Faison: No, that’s not true. [“I’m keepin’ it real”] was not in the script. I put that in the script. She didn’t write “I’m keeping it real.” I heard that from my neighbor. Some kid in my neighborhood said, “Just keep it real. Just make sure you keep it real.” And I was like, “Oh. That’s what the kids are saying now?” And so I put that in there myself: “I’m keepin’ it real. Because I’m keepin’ it real.” You didn’t write that — dammit, Heckerling! Come on, old buddy! Everything else: “Look at Lawrence’s head. It’s the bomb.” That’s all her. “I’m keeping it real,” unfortunately, was me. Sorry, Amy. I can’t let you have that one.

Heckerling: At one point [in the scene], I wanted to see that the party was getting later into the evening: somebody would be throwing up in the swimming pool, and a couple would be making out in the pool, you know. Me and the ADs were saying that if any of the extras wanted to play a couple in the swimming pool that would be making out, they would get extra money for that because they would be wet. So, you know, a couple of people volunteered: a cute guy and a cute girl. And I thought, well, they’ll make a nice couple. So we asked them if they wanted to do it, and they looked at each other and thought, “Yeah, okay.” Years later, I was walking down Melrose and I hear some people going, “Amy! Amy!” And I turn around, and it was them. They met that night. They’re engaged. She shows me the ring that’s been in his family … They became a couple, and when I met them on the street, they were engaged. I don’t know how that marriage worked out, but it was really sweet.

Meyer: I think every scene in that movie we had such a good time making. I mean, it wasn’t a real party but every scene was just a fun gathering.

Faison: We had a blast making that project. So the party scene, it literally felt like a party.

Coolio: I remember going to the premiere — they had it on the beach — and basically getting white-boy wasted.

Faison: That was my go-to when I wanted to be with a girl. I’d say, “Come over and let’s watch Clueless.” Absolutely. Clueless was the ultimate wingman. [Girls] loved the movie. They didn’t give a shit about me being in the movie, they just loved the movie, period. I just used it as, yeah, let’s watch the movie … I mean, I didn’t start getting girlfriends and stuff like that until Clueless came out. So you know, it worked well for me. It’s because I kept it real, that’s exactly right. Because I was keepin’ it real.