Pt. I can be found here.
When I discovered that my new friend, Carrie, had been a finalist in the 1992 Sassiest Girl in America contest, I screamed and freaked out and she handled it much more nicely than the 1990 Sassiest Girl, who to be fair was not my friend and I had ambushed her in the creepiest way possible on the first day of school. She showed me the magazine, and I remembered looking at her picture back in January of 1993 along with the pictures of the other five finalists, realizing they had that It, I did not, and I never would. Now here in was sitting in the living room of one of the sassiest AND SHE WAS MY FRIEND. I couldn’t believe it.
Carrie and I are still friends (see above!) She’s still pretty sassy—she’s funny, smart, beautiful, and is an amazing artist. She recently sold her half of the eco-friendly greeting card and stationery company she co-founded in 2006 in order to do some full-time mothering of an insanely adorable and brilliant toddler. When I told her I was writing about Sassy and the Sassiest Girl in America contest, she was delighted and agreed to sit with me and let me interview her. Was I finally going to be able to crack the Sassy code at last? What DID the Sassiest Girls have that I hadn’t had? What was it like in the Sassy offices? Were the writers as cool as I had imagined? I had to know; Carrie kindly humored me. She also pointed out that in her Sassiest Girl write-up, they apparently did not understand her handwriting on the application, in which she wrote that she cut her own hair, and included in her bio that she “eats her own hair (really.)” Carrie was and it still horrified by this. “Why would they present that as something cool and interesting?! That would mean I had serious physical and emotional problems, Sassy.” True; what the hell, Sassy? I do remember thinking that was weird when I read it in 1993; she edited it to “cuts” herself with a ballpoint pen in the copy she brought to our interview at a coffee shop in Brookline, MA.
Me: Let’s talk Sassy! What year did you enter the Sassiest Girl in America contest?
Carrie: The summer of 1992, between my last year of high school and going off to college. I was bored all summer and needed something to do. The competition that year was creating a “perfect person,” combining the characteristics of “more than four but less than fifteen” other people.
Me: OH, I REMEMBER.
Carrie: I sewed a rag doll out of scrap fabric and labeled all the parts, as described in the magazine. You’re welcome to take this with you; my mom bought thirty copies, so there’s a stockpile.
Me: [Speechless at both the brilliance of making a doll instead of just writing down some plagiarized crap AND the idea of owning a copy of Sassy.]
Carrie: I actually had a shoebox, and the brand of shoes was She’s Sassy. I suspect that might have gotten my feet in the door, HAHAHA. I mailed the doll away and kind of forgot about it.
Me: What kind of pictures did you send in?
Carrie: My mom and I totally did a photo shoot. The only one I can really remember is cuffing up my jeans, standing on the first step of the pool, and acting like the water was cold. I was wearing my favorite button down paisley shirt and probably some horrible beaded necklace.
Me: Of course.
Carrie: It was 1992.
Me: It was the jewelry that was available. How did you find out you were a finalist?
Carrie: They called! It was Kim France!
Me: (insane, long gasp) Whaaaaaat?!
Carrie: I KNOW. And she was totally all business on the phone at first, so I was all business back. She was like “This is Kim France. I’m calling from Sassy magazine for Carrie Holmes.” So I was like, “Hello. Speaking.” I remember later she commented that I was totally blasé on the phone.
Me: Were you in shock?!
Carrie: I was kind of in shock. She asked if I could come to New York the second week of September, and I remember expressing concern about that. I said, “Well, I WILL have just started COLLEGE!” and she was like “I think your school will be ok with you taking time off…” Thanks for the reassurance, Kim France! I was kind of a goody-goody.
Me: So I want to get into that a bit. I see here that you “started a group called the Commune with a bunch of friends who decided they wanted to hang out and have fun without drinking or doing drugs.”
Carrie: So, I didn’t start it, and it wasn’t really a club. It was just a bunch of kids that hung out and didn’t drink. We watched a lot of movies, hung out in my parents’ den, went to the local playground—things you do when you’re a teenager in a small town and not drinking.
You: You are from Florida.
Carrie: Titusville, Florida. Boring, conservative, weird little town.
Me: What was your relationship to Sassy?
Carrie: Sassy was the only magazine my mother would let me subscribe to. Looking back, that was pretty cool of my mom and not something I would have expected from her at the time. She vetoed Seventeen and she vetoed Young Miss, which became YM. But Sassy was ok.
Me: For me, personally, I learned about “alternative” culture in general from Sassy. Sassy, along with college radio, was probably my first exposure to that type of thing. Would you say the same?
Carrie: Yeah. A little bit earlier I got into some alternative music and I would pick up music magazines from time to time, but that was really erratic. There was no alternative culture in my town. There were a handful of us, and we were all friends. It was definitely my first exposure to alternative fashion as something that people did. When I was fourteen, I wanted my hair cut in a reverse bob—short in the back, long in the front—and my hairdresser wouldn’t do it. She’d never seen it, didn’t understand it, and just said “No.” That’s when I started CUTTING my own hair.
Me: Not eating it.
Carrie: Not eating it. Thank you, Sassy. But yeah, there were girls in Sassy that were dressed the way I wanted to dress and looking back, I think it must have helped my mother. Initially, my mother’s reaction to me was “This is weird.” Between junior high and high school, I first got into music and I became obsessed with the Cure. I started teasing my hair, trying to look like Robert Smith. It didn’t go over so well with my mom or the general public.
Me: Sassy gave you a point of reference to show that other people were into this, too? (“Cool voice”): “In NEW YORK, Mom…people look like THIS!”
Carrie: Yes! It was a way for her to accept the way I was looking.
Me: It legitimized it.
Carrie: Yes; it wasn’t just her daughter being a lunatic. It made me ok.
Me: “Also, I have a no drinking no drugs club that meets in our den, Mom. I’m ok.” So…was this your first trip to New York?
Carrie: Yes. My middle brother, Tim, had been to New York a few times before, so I asked my parents if he could be my chaperone. I got to go with my brother instead of, like, my mom.
Me: That is very cool. How old was your brother at the time? [I do not have an older sibling and actually thought about this a lot when thinking about winning the contest.]
Carrie: He was 22.
Me: [Impressed.] Oh, COOL!
Carrie: Much cooler. Although, I was surprised, there were only two girls that came with their moms. Everyone else had a cousin or sibling.
Me: I remember noting that every year when trying to crack the Sassiest Girl code and thinking “Oh my GOD, I would have to bring MY MOM. HOW UNCOOL.”
Carrie: I know. If Tim hadn’t been to New York, I would have had to bring my mom and it would have been a totally different experience.
Me: But you showed up with a cool 22 year old.
Carrie: Yes, gay older brother, knew about nightlife, knew New York.
Me: So you had the coolest chaperone.
Carrie: Actually, the girl who won, Stephanie, had a super-cool older sister.
Me: Of course. Was there a clocking of the chaperones? Like, ok, cool, cool….
Carrie: “Oh, had to come with Mom. Sorry.” Yes.
Me: I remember being weirdly stressed about that.
Carrie: It’s a major consideration. Who wants to go to New York with your mom when you’re seventeen?
Me: No one. Was Tim psyched to be on board?
Carrie: Yes. I felt like Tim knew New York so by extension I knew New York. I could take the subway, I could hail a cab—all of these things that for a small town Florida girl were mildly terrifying. If I had been with my mom, we might not have made it to Sassy at all.
Me: YES. [Remembering being a small town New Hampshire girl; the subway system and cabs also weighed heavily on my mind.] So, you fly to New York…did they pick you up at the airport?
Carrie: They sent interns to pick us up at the airport. They were sitting on the ground outside my gate, holding a sign and looking cool and bored and ratty.
Me: Did you go right to Sassy from the airport?
Carrie: I’m trying to remember where we went first; we had to do all of these weird focus groups.
Me: THAT’S WEIRD AND INTERESTING!
Carrie: I think that’s actually what we did first!
Me: WHAT?! What were the focus groups focused on?!
Carrie: They were about…products! You know, “What do you think of this deodorant?” I remember the girl who won, Stephanie, was like “I hate roll-on deodorant!” and they were like “Why?” and she was like “It feels like somebody licked my armpit!” and I was like “You are hilarious. And accurate.” I remember for some reason one of the deodorants was, I think, a German deodorant called Fa.
Me: I remember slightly sexy Fa commercials.
Carrie: And we were like “No. Not into Fa.”
Me: Sassy killed Fa. How long was the focus group?
Carrie: It felt like forever.
Me: This is a huge exposé as far as I’m concerned. THE SASSIEST GIRL IN AMERICA CONTEST WAS ACTUALLY A GIANT FOCUS GROUP!
Carrie: Yeah, it was in a boring room with a huge table and the six of us were just like “Well, here we are. Talking about deodorant.”
Me: And this was first! Before you did anything else! They made sure this happened, if nothing else! It was their top priority!
Carrie: I’m sure there was some sort of sponsorship situation going on. So then we went to the Sassy office and did personal interviews.
Me: Who did the interviews?
Carrie: I remember Margie…
Me: Eeeeeee! LOVE MARGIE. [I still love Margie, who now goes by Marjorie.
Carrie: She was my favorite!
Me: She seemed the most down to earth of all of them, as if she would be the most approachable and normal.
Carrie: She was such a warm person.
Me: I’m so glad that’s actually true and that it doesn’t turn out that Margie is a giant bitch.
Carrie: Margie was not a bitch.
Me: Thank God. Jane Pratt?
Carrie: I met Jane for about two minutes. Jane was really not involved.
Me: Hmmm. Interesting. What did they ask in the personal interview?
Carrie: I had to expand upon my choices for my contest entry and talk about what I did and what my life looked like. I felt comfortable within a few minutes; I didn’t feel judged. It was just kind of a chat, and they were adults, but they had a very youthful demeanor. Looking back, I see that was because they were in their early twenties!
Me: Yes! Not that much older than you at the time, actually. So, looking at your entry, I noticed that you were really into nuclear disarmament! That was your cause! Did you talk about that?
Carrie: Yeah, I did. It started because my oldest brother, Dan, was really into it; that was really his thing. It started in 1984 with the Great Peace March from California to Washington, DC, and then a faction split off and came down to Florida because they were protesting the nuclearization of NASA. My town was a company town for NASA, and suddenly they wanted to start sending up missiles and doing all sorts of nuclear testing. My oldest brother didn’t have a great relationship with my parents at the time, and so my parents, in an effort to connect with him, said yes when he asked if the people coming down from DC could camp in our backyard. We wound up with about thirty people camping in our yard, and a lot of them ended up moving into the house for about a week because they had a cold or were 78. There were people everywhere, and it was incredible. It was a really good experience for me. It was the first time I heard of veganism. One woman was eating raw garlic because she was getting a cold and that blew my mind.
Me: So your introduction to social justice took place because it was literally happening in your own backyard.
Carrie: Social justice everywhere. That became my cause. It was partially because I idolized my older brother, but I had a personal link to it, too. I’m sure you remember at that time that nuclear war felt absolutely inevitable.
Me: Yes. Bombs are coming, no question about it, any moment, nuclear war…now here’s an episode of ALF. Were any of the other finalists particularly socially active?
Carrie: No, not that I remember.
Me: So maybe that was your in—the Social Activist. I noticed that when I was reading the other girls’ bios—no one else seemed to have as clear a goal for their prize money [which in part had to go to charity.]
Carrie: Yeah, maybe.
Me: So did they take you out after the focus groups and interviews?
Carrie: Yes! We went out to dinner at El Teddy’s, which was a funky New York restaurant. It was in Tribeca. [Googles it.] There it is, “iconic façade of 80’s and 90’s New York.”
Me: Oh, wow! Yes. You had arrived. They took you to an iconic façade.
Carrie: It was amazing. It was an incredible experience for someone like me. I sat next to Margie….
Carrie: Yes. Margie on one side, Sassiest Stephanie on the other. And I THINK they announced the winner that night.
Me: Was it a surprise win?
Carrie: Not really, but two of the girls were kind of pissed. [Points out one.] This one was SUPER pissed, actually.
Carrie: Yeah, she didn’t do anything else. The next day she came to the photo shoot and then left immediately.
Me: “I should have won. Bye.”
Carrie: She never talked to me anyway, so whatever. [Pulls newspaper clipping from the back of the magazine.] Here I am in my hometown newspaper, hanging out with Stephanie.
Me: That’s Stephanie?! Oh my God. Ok, so Stephanie looks like the most early 90’s-est of early 90’s cool girls. She is all of 15 years old and basically looks like a cute skater boy.
Carrie: Yes. She was so cool and nice and smart and sarcastic in the right ways. Not mean, not bitchy, just funny.
Me: Talk about the photo shoot.
Carrie: It was the next day and it was SO LONG.
Me: So, obviously they had a floral dress theme, which is again so early 90’s it hurts. Did you get to pick your clothes?
Carrie: No. They had asked our sizes in advance and handed out the dresses at the shoot. We went to Coney Island. I wore Birkenstocks all the time at that point, and I had no socks. They put me in brand new Doc Martens and THEY had no socks, so my feet were in shreds by the end!
Me: Did you have to give back the shoes?!
Carrie: Yes! I was like, here you are, these are filled with blood. So yeah, hours of pacing up and down the boardwalk, bleeding and holding hands with this girl.
[“Stay” by Lisa Loeb starts playing over the coffee shop stereo and we die laughing.]
Carrie: Ok, so wait, I am wrong…we got MAKEOVERS first.
Me: [reading about the makeovers] “Carrie Holmes, the most daring of the group…”
Carrie: I was the only one who was like “I’m at a fancy New York salon! Do whatever you want!” We got makeovers at Louis Licari.
Carrie: Right?! And we got a tote bag full of products and one was a hairbrush that said LOUIS LICARI on the back. I treasured it for years. So then we had a shopping spree.
Me: Where did the take you?
Carrie: Merry Go Round.
Carrie: It was kind of horrible. There was really nothing in my size—I was like a 14.
Me, speaking as Merry Go Round: “We don’t know what that is.”
Carrie: No. I probably could have squeezed into some spandex dress, but that wasn’t my jam anyway. So I wound up buying men’s clothes.
Me: Which was probably pretty cool.
Carrie: Yeah, I bought Cross Colours jeans in dark green.
Me: Well, it was a pretty unisex time for fashion in general. Like I said, Stephanie looks like a cute boy in this picture. I had a LOT of men’s shirts during that time period. So when it was all over, did you ever hear anything from Sassy again? Did you keep in touch with any of the other girls?
Carrie: No. It was pre-email, I had just started college, so…I just went home.
Me: Do you feel like it changed your life in any way? How do you feel about your time as one of the Sassiest Girls in America?
Carrie: For me, it gave me a boost of confidence. I was starting college and I was very uncertain about all of that. I think it gave me affirmation that I was smart, clever, and interesting.
Me: So you do feel like the contest judged you on your personality.
Carrie: Yeah; it had nothing to do with how I looked or dressed, and for me, I had so many troubles with body image, starting at age eight. For years, I had this feeling of “If I wasn’t fat, my life would be different. If only I could be thin, people would know I was smart.” I loved talking with Margie because she was MARGIE, but she was also on the heavier side. She wasn’t fat…Margie, I’m not calling you fat! But, she could definitely relate to me.
Me: She was in this very fashionable world where everyone was a size two…
Carrie: And she wasn’t. And, you know, if you look at this picture of me, you see that I was actually not fat. I’m not like this [thin] girl or this [thin] girl, but I’m not huge. But my perception was so skewed that I didn’t know that.
Me: Everyone is dressed pretty much the same, although I see Stephanie didn’t have to wear a floral dress. [Her dress is a long, striped t-shirt. Of course.] Everyone looks natural and normal; no one looks like a model.
Carrie: Yes. Oh, and P.S., I found out my high school boyfriend and his friends used to call me The Sixth Sassiest Girl in America, which I find amazing. I just learned about this a year ago on Facebook.
Me: Were you like “Clearly I’m third!”?
Carrie: Clearly, third. Maybe fourth. But yeah, Sassy showed me…well… just a little background. My mom is awesome. But, when I entered the contest, she said “Just so you know, there’s going to be thousands of girls entering from all over the country, so don’t be disappointed.”
Carrie: My mom knew I was smart, but she thought I was a big fish in a small pond. We lived in a small, shitty town—they still live there and seem to like it, I don’t know why. It was always like “Well, you’re fine.” I get it, I understand what she’s trying to do, but also there this a part of me that wished she could have been a little more enthusiastic. When I won, she was completely blown away and totally baffled.
Carrie: Yeah! I remember her going “You’re kidding.” And I was like “No! They just called me!”
Me: “I was just on the phone with Kim France!” I guess we’re always looking for what we don’t have. My mom was like “Obviously you’re the best!” and I was like “I’m really not, Mom, but I feel like I could be close, but your opinion doesn’t count because you’re my mother.”
Carrie: Right, and I was like “See, Mom?! I really am cool and smart!” It really is something I’ve carried with me throughout my life. I’ve got a little somethin’. It’s in there.
Me: And winning made that clear to you?
Carrie: Definitely. When I finished college and came to Boston, my first job was at an ad agency, and they were lovely people, and I hated the work. When I went to apply for the display position at Urban Outfitters, which at the time had a total of fourteen stores and each store had an individual artist working for them, I had the Sassiest Girl in America on my resume as kind of a joke at the bottom. During the interview, they were like “So, you went to Flagler College and you studied art…BUT TELL US ABOUT SASSY!” So it really became the stepping stone into my career in window display design, which I did for a decade.
Me: And therefore your entire career as an artist and designer.
Me: That’s huge!
Carrie: It was a significant thing.
APPARENTLY it turns out that the secret of winning the Sassiest Girl in America contest was to not only have a cool older sibling, but to actually cultivate a meaningful inner life free from plagiarism, pay attention to and participate in the world in a significant way, and to BE YOURSELF, which was and is still advice that irritates me and that I have a hard time accepting. I was shocked to discover the focus group aspect of the contest, but of course Sassy was not ACTUALLY the independent urban feminist paradise I imagined it was—it was, in the end, a magazine that made its living off of teenage girls. It was better than the other magazines of its ilk, but it still wanted to sell as much deodorant as it could. Furthermore, Carrie got from the contest what I already had—she wanted her mother to believe in her and to see her as special and worthy of winning a contest. When that came up during the interview, I felt like I had been smacked. I always had and still have my mother’s support and admiration, so I took it for granted and dismissed it. I still have a hard time accepting that, too, but I’m working on it.