Toxic: The Britney Spears Story

Chapter 2: Lucky

ARCHIVAL: [screaming] 

BABS GRAY, HOST: It’s the early 2000s. And if it’s a weekday in Times Square, this is the scene. Giant screens blast ads for fast food. Cell phones. Banks. Yellow taxis whiz by a pack of teenagers squeezed together on a median. 

TESS BARKER, HOST: They wear bucket hats and spaghetti strap tanks. They scream with that enthusiasm you only have before you’ve learned about taxes or paying rent. They lift up their arms in praise, wave poster board signs. And they all look up to one place - the studio perched above them. 

DAVE HOLMES (ARCHIVAL): Please welcome Britney Spears! 

ARCHIVAL: [crowd cheering, music plays] 

TESS: This is TRL. Or Total Request Live. It’s on MTV. 

BABS: And there’s nothing else like it on television. Every day, they break down the top 10 music videos. But it’s way more than just that. It’s a hang. It’s THE hang. A celebrity could drop in at any moment. Wild shit is always going down. This is the place where Lindsey Lohan performs an angry rock ballad about her relationship with her dad. Where Beyonce and Jay-Z appear together before announcing they’re a couple. It’s the house party of your dreams. And every kid in America is invited. 

TESS: And if you’re lucky enough, or have cool enough parents, you too might make the pilgrimage to stand outside the TRL studio. 

DAVE: Literally the first time I went up to the studios to wave, there were a whole bunch of kids who were just like, “YEAHHH!!!” I used to say I feel like a teenage Mussolini at the windows. I could just walk up and put an arm up and people would go “AHHH”! 

BABS: This is Dave Holmes. Now, Dave is an author, actor, and podcaster. But back in the day, he was a VJ at TRL. That stands for “video jockey,” kids. 

TESS: Dave said that working at TRL was basically the most fun job he could possibly have had in the early aughts. Remember, at this point, there was no Twitter. There was no YouTube. If you wanted to promote a new single, you took your ass to that little studio with the big glass walls. 

DAVE: We were, like, this super cool clubhouse for a few years, where, like, literally everybody had to come by.

TESS: Everybody who’s anybody. And in Dave’s hey-day at TRL, nobody was bigger than Britney Spears. 

DAVE (ARCHIVAL): Everyone say hi to Britney! 


BABS: Here’s Dave in 1999 outside Times Square with a huge crowd of Britney’s fans. 

DAVE (ARCHIVAL): I’m here with Stephanie. She’s got a question for you. STEPHANIE (ARCHIVAL): Hi Britney, you’re so cool. My question is: since you’ve been in the business for so long, what’s the hardest audition you’ve ever HAD? BRITNEY SPEARS (ARCHIVAL): Probably, I had to audition for Jive Records. I was so nervous, because I’m so used to…. [FADE DOWN] 

TESS: Britney appeared on TRL 86 times! That’s more than any other celebrity. 

TESS (TO DAVE): What was your first memory of meeting or seeing Britney Spears? DAVE: Well, I remember hearing the name, or seeing the name before I met her. And it was on our MTV, AOL message boards. 


BABS: Oh yeah. AOL. Some of us may remember these message boards. You had to hog the family phone line to log on and argue about boy bands or Buffy the Vampire Slayer’s romantic life. You know, important topics. 

DAVE: You know, the 14-year-old girls who populate this with comments are not nice. But there was like a subfolder or something about Britney Spears before I knew who she was. A lot of threads with with the title Britney Spears sucks, like "SUXS." And I was like, I don't know who that is, but I bet she doesn't suxs. I bet she's pretty good. 


TESS: In our last episode, we told you a little bit about the people who control Britney’s money now. She’s an exceptional earner. A truth… and a lyric from her song Piece of Me. But in order for everyone to take a piece of Britney’s fortune, she had to earn it first. 

BABS: So let’s go back to before it all happened. What’s it like to be a kid with an eye to stardom? And if you become that star, if you live the life so many people only dream of, what will everyone expect of you in return? 

TESS: Grab a Frappuccino. We’re getting into it on this episode of Toxic.


DAISY: We had a classmate who would sit in the school bus and sing songs from the show she was understudying in at the top of her lungs. Nobody really knew who she was. And we were all performers. So no one was, like, impressed. 

TESS: This is actress Daisy Eagan. She’s talking about the middle school she attended in New York called Professional Performing Arts School, or PPAS. 

DAISY: We were all like, yeah, OK, so we can all sing. And I realized many years later that that was actually Britney Spears. 

TESS: That’s right. Daisy went to middle school with Britney. 

TESS (QUESTION): I'm only going to ask you to do this because you're a professional and feel free to say no, but could you sing a couple of lines from that song that Britney was singing on the bus? 

DAISY: Oh, from “Ruthless”? 

TESS: Yeah. 

DAISY: Yeah. I have to lean back. [SINGING] I was born to entertain. 

TESS: Thank you. 

DAISY: That is, that is my one impression of Britney Spears at 11 years old, on the back of the school bus. And we were all like, “Yeah bitch, we all were, quiet down.” 

BABS: For some people it takes decades to get your big break. That wasn’t quite the case with Daisy. 

DAISY: So basically the third professional gig I had was the Secret Garden on Broadway. I had just done Les Miserables on Broadway. 

ARCHIVAL: And the Tony Award Goes to… DAISY EAGAN! 

DAISY (PRESENT DAY): I won a Tony Award when I was 11, which was bananas. DAISY (ARCHIVAL): I don’t think I can talk! [fade down] 

BABS: Oh god, so cute. Ok. We wanted to talk to Daisy because Daisy and Britney have something really important in common — they both spent their childhoods at work. Performing on stage. That’s why they ended up as classmates.

TESS (QUESTION): So what's the function of the school? Is it for kids that are actively working or have aspirations to work or both? 

DAISY: Yeah, Professional Performing Arts School was started as a professional training school that catered to kids who were working, but was training kids who weren't necessarily working. So a lot of us were on Broadway at the time. And this was like a weird time on Broadway where there were tons of kids, just a lot of kids who, like, sort of came through New York for like a season would go to PPAS. 


TESS: Britney was one of those kids. Lynne Spears talks about this time in her 2008 memoir titled “Through the Storm: A Real Story of Fame and Family in a Tabloid World.” The book gives a lot of insight into Britney’s childhood, and it actually goes all the way up until the weekend Britney is conserved. 

BABS: Some Britney fans call it “the Bible.” There are poems. There’s a chapter called “Mama, I’m Pregnant.” There’s an anecdote about Lynne firing a shotgun at some of her ex-husband’s beers in the backyard. 

TESS: In the book, Lynne says Britney loved to perform from the time she was two. So Lynne signed her up for dance lessons. Britney went on to win singing competitions. She was in a beauty pageant. When Britney was 9, Lynne took her to New York so she could try to make it big. And it didn’t take long for Britney to book a gig -- as an understudy in that off-Broadway show “Ruthless.” 

BABS: The role was a huge break for Britney. But it was also a way for Britney, her mom, and her baby sister to get away from their hometown of Kentwood, Louisiana. Britney’s father, Jamie, was a drinker. Lynne says in her book that he could become violent when he was drunk. New York let them escape the tension at home. 

TESS: In the evening, Britney would be at the theater. During the day, she was at PPAS. 

DAISY: She was mostly ignored at school because she was sort of -- she was only there for a little bit of time. And again, like, I hate to say this, but like she was, quote, only an understudy in an off-Broadway show at that. And the rest of us were like, had been in three Broadway shows or whatever, so we just -- it's terrible to say, but I really do think that, like, she just was sort of a nonentity in a way. I think she was pretty quiet. You know, she was a girl from Louisiana or wherever who is, you know. A little fish in a big sea. 

BRITNEY (ARCHIVAL): Welcome to my hometown of Kentwood, Louisiana. It’s a small, small town, about an hour north of New Orleans.

TESS: A couple years after New York, Britney would be cast on a kids’ variety show. The Mickey Mouse Club. It helped launch her career. Here’s Britney on the show talking about her Southern roots. 

BRITNEY (ARCHIVAL): Where I come from is country, and when I get back home I start talking country again. Stuff like “yonder,” and “hey y’all” or “what y’all doin’.” Stuff like that. 

TESS: Life as a child actor was way more fast paced than life as a kid in Kentwood. Honestly, the schedule Daisy described sounded dizzying to us. And we’re adults - who have access to cold brew. 

DAISY: You could be looking at a kid who by the time they get to their show at night has already done four auditions is now about to do, you know, a two and a half hour Broadway show and then you're all wound up and you can't get to sleep until after 1:00 and then you're up at six to go to school the next day. I mean, I think a lot of us were sort of zombies for a lot of that time. 

TESS (QUESTION): I mean, yeah, I acted when I was a kid, too, you know, unsuccessfully. But it’s a tough hustle,you're just constantly going to auditions, getting your hopes up. It’s just a lot. I can't believe that I went through that as a kid. 

DAISY: Yeah, it's rejection after rejection, after rejection, after rejection. And as a kid, it's like you don't really know why necessarily. You know, when I was a kid, if I didn't get a job, I was just sad because I was hoping to do that job. It wasn't like a financial crisis, you know? And I know for a lot of these kids, they do have parents who let them know how much of a financial part they play in the family, and so it is even more added pressure to make money at that age. 

BABS (QUESTION): Did you know any kids whose families depended on them to make money? 

DAISY: I mean, no one was going to come out and admit that, but I knew kids who had, you know, single parents and the parents were dedicated to their kids' careers. So where was that money coming from? 

BABS: For the Spears family, money had always been tight. Jamie had tried and failed at running various businesses, and the income from Lynne’s daycare never seemed to make up the difference. But in her book, Lynne is adamant that the family wasn’t relying on Britney to dig them out of their financial hole.

TESS: Britney was making money from the time she was in junior high. We don’t know if she got to keep all the money she made for herself. Kid performers don’t directly receive the paychecks they earn. They generally go to their agents and then the parents. 

BABS: There are some protections in place when it comes to young performers. There’s a law that states a percentage of all their earnings must be placed into a trust that they’ll get access to when they turn 18. 

TESS: No matter what way you slice it, for a kid performer to be successful, there have to be adults involved. Someone has to drive them to the auditions, submit them to record labels, all that. We asked Daisy if she was treated any differently by the adults in her life after she won her Tony. 

DAISY: I wouldn't say I was treated differently, but I would say that people did start to sort of come out of the woodwork and want to, in retrospect, take advantage and like, sort of hook on to what they thought might be, you know, a cash cow. We had people who came forward and they were like, we want to make a pop album with you. And I 

remember we had a meeting and they played us some demos. And we were like, what? None of that makes any sense. 

TESS: Entertainment is one of those careers where, the earlier you start, the better. You can picture how a precocious young performer could go from tap classes to y’know TRL. 

BABS: And every performer, even kids, can become a sort of mini industry. They’ve got agents, managers… a lot of people whose paychecks depend on that kid. 

TESS: And again, it’s a lot of rejection. It’s a lot of pressure. 

BABS (QUESTION): What do you think that manifests itself as an adult, that all that rejection and that kind of like going in and being judged by adults every day, like what does that look like in your personality later or your mental health later on? 

DAISY: I mean, I can say for me that, you know, certainly low self-esteem, you have to work so hard to combat that, because it's exhausting to constantly be under a microscope like that 


BABS: Daisy didn’t stay in contact with Britney after they both left PPAS. But a few years later, an old classmate hit Daisy up. He had been trying to reach out to her for a while. 

DAISY: He said, you know, I didn't know what happened to you. I couldn't find you. And I asked Britney if she knew your whereabouts. And Britney apparently said, oh, I don't like her. She is a bad girl. [laughs] You know, I've been cutting school and smoked cigarettes, and I was, you know, I thought I was a badass.

BABS: Not long after this… Daisy saw Britney. On a giant billboard. 

DAISY: She had her Pepsi billboard up in Times Square with her thong showing. And I just thought it was such a, it was just ironic, it was ironic that, you know, there she was calling me a bad girl and she had this image of like, you know, naughty, naughty Britney. 


BABS: Yup. In the few short years since junior high, Britney had become a worldwide phenomenon. At 16 years old, when most kids’ biggest goal was passing their driver’s tests, Britney dropped the year’s number one single. “...Baby One More Time” went platinum 14 times over. Britney had gone from that kid singing on the back of the bus to full-fledged teen dream. Showing her thong on a Pepsi Billboard just a few hundred feet from Dave Holmes at MTV. 

ARCHIVAL Dave & Britney 

DAVE (ARCHIVAL): We got some belly news, from what I understand. 

BRITNEY (ARCHIVAL): Oh yeah I pierced my belly 

DAVE (ARCHIVAL): Oh let’s have a look can we see? 


TESS: Here’s Britney on TRL with Dave in 2000. I mean...Britney basically invented belly buttons. And rings. 

DAVE: Oh, OW! Oh, wow. We’re making a big announcement. 

BRITNEY: It hurt so bad. The needle was this big. I was like holy smokes. I can’t believe I said holy smokes on TRL. Now everyone knows what a goob I am. 

DAVE: It’s OK. 

BABS: Dave interviewed Britney a half dozen times while he worked for TRL. They’d usually talk about whatever her new hit was. 

TESS: Sidenote: We would love to play those songs for you in this show… but uh, her label never got back to us about how much that would cost. Plus, to be honest, we don’t really want to shell out thousands of dollars to license those songs when we know that the money goes straight to Britney’s conservatorship, not Britney herself. 

BABS: Ok back to TRL. Britney would also occasionally teach Dave some dance moves. f\ 

DAVE (ARCHIVAL): Can you teach me the shimmy? 

BRITNEY (ARCHIVAL): Yes I think I can. 


BRITNEY (ARCHIVAL): So you just walk forward and you just shimmy like this. DAVE (ARCHIVAL): Like this kind of a thing?


TESS: Britney is a phenomenal dancer. Her songs and vocals are amazing, of course... But her dancing is what’s always set her apart. She punctuates accents in the music with hip thrusts and high kicks that defy physiology. The music seems to roll through her body and blow through her hair as she gives it her signature flip. Her early music videos and live performances showcased this ability to pull off incredible choreography that was distinctly her style. 

BABS: Britney’s dance moves were not that innocent - they were always fairly suggestive, even if she was wearing a schoolgirl uniform. Britney was immediately known for toeing this line. We talked with Dave about this, and working with Britney in general. 

DAVE: The image was very carefully constructed to be both innocent and very sexy, so like sweet, but you can almost always see her navel, which is like, not a bad thing, but but it was like, you know, it was they they constructed the image very carefully in order to have it both ways, to have her be like a sex object, but also unthreatening so that the teenage girls didn't revolt, or their parents. 

TESS: And did you see any of the male artists that she was contemporaries with having to kind of dance that line between being both sexy and virginal? 

DAVE: No, it didn't matter. Like all of the boy bands could thrust their pelvises to their heart's content, they could have their shirts off and their shoulders out and all that, you know, all of the time. 98 degrees was, you know, a workout video disguised as a boy band. And they didn't have to worry about it. Yeah, boys always have the option to be as sexy as they feel like, but girls have to do the tightrope walk. 

BABS: It’s hard to overstate just how big Britney was at her height. From 1999 to 2003 she was everywhere. Not just on billboards in Times Square, but magazine covers. Commercials. If you got a soda at 7-Eleven, you know it came in a commemorative Britney cup. 

TESS: Being a pop fan around Y2K allowed you to try on different identities like hats. It really mattered which Spice Girl you thought you were. I, for example, really saw myself as Ginger Spice, but blonde. Or how about which Backstreet Boy was your favorite? 

BABS: Well, I was all about AJ, the bad boy. It felt like by picking him, I was really rebelling against the establishment in my own 14 year old way. Of course, others may have chosen the hearthrob, Nick, or the sensitive guy Brian. But you know, Brian he’s into QAnon now, so I think I made the right choice. 

TESS: Dave Holmes said he thinks boy bands and girl groups of this era had it easier than solo stars like Britney - they could show up on MTV and play their assigned parts. But, Britney had to deliver the whole package by herself. Here’s Dave again, and FYI, you may hear a cameo from Dave’s dog.

DAVE: I remember when she came in with the massive entourage and huge expectations, it was like when the boy bands came in, but it was just her and the entourage. But like when it would come to the on camera stuff, it was just her. And I remember thinking, like the amount of pressure this kid is under. Because the boys can all play off each other. And if one of them says something dumb, then the other ones can make fun of them. And then that's how they create their image and their personalities and whatever. But like, if she said something dumb or if a hair was out of place or if the pants didn't fit right or whatever, it would be like a scandal. And, you know, it's all her and she's real young. 


BABS: Britney may have been solo on camera, but she did have a team backstage to do her makeup or style her crop top. Her manager would be there to deal with the business stuff. From what Dave saw, Britney’s team seemed to mostly consist of these industry types-- not family. 

DAVE: For all of the times that she came to the studio and for all the people that came along with her, I don't remember seeing her dad. I don't think I've ever met her dad. I don't think I ever met her mom. Yeah, I don't think I've ever seen Jamie Spears in person ever. 

TESS: Britney’s dad was not a part of her early entourage. Her mom was there when she could be. Britney was 16 when she recorded her first album in Sweden with mega-hit maker Max Martin. She was only accompanied by a close family friend. Lynne writes that she had to balance Britney’s success with taking care of her youngest child, Britney’s little sister Jamie Lynne. 

BABS: And maybe all this independence is the reason why, when Dave interviewed Britney on TRL, she always struck him as pretty mature. 

DAVE: I remember thinking like, oh, she's putting me at ease. She's making me feel better. She was very, very professional and very polished. 

BABS: Here’s Dave talking to Britney in 2000 about her two Grammy nominations. 

DAVE (ARCHIVAL): Which one — we’re tight, you can be honest with me, which one would you rather win? Best pop performance female or best new artist? 

BRITNEY (ARCHIVAL): Um, probably best new artist. I’ll be just happy to be there and perform, seriously. 

DAVE (ARCHIVAL): I’ll be in front of the TV, rooting for ya! With my little britney sign. That I’ll make [FADE DOWN]

DAVE: And, you know, if I'm on air, I'm nervous. So I have to -- and I'm, you know, twice her age and I've been at it for a while and it's my job. I just couldn't imagine the amount of pressure that she was under and facing it all without any, you know, real support, that I could see. 


BABS: Britney was pulling it off. By 20 years old, she was at the epicenter of an entire music empire. Her fanbase was exploding. And so was her net worth. According to Forbes, in 2002 Britney brought home a paycheck of $40 million. The world was consuming anything and everything Britney Spears. And her impact was profound. For some people, she was selling more than just music. She was selling an escape from everyday life. 

TESS: Eventually, some of those teens holding signs outside of TRL would turn into the adults holding banners outside her court hearings. What is it about this girl with blond highlights and a southern drawl that could inspire such lifelong devotion? 


MATT STOPERA (ARCHIVAL): Slave for Britney, slave for Britney! Hit me Britney one more time. Woo! Britney forever! 

TESS: This is Matt Stopera in 2003. He’s running around his suburban neighborhood yelling “Britney” for another show on MTV: “Fanography.“ His episode is about… you guessed it, Britney Spears. 

MATT (ARCHIVAL): My name's Matt and we're in Synecdoche, New York, and I am the biggest Britney fan in the whole entire world. Come in right here and we come into Britney Paradise. 

TESS: Matt is 14 here. He has cargo shorts and a polo his mom might have bought him at Old Navy. He’s taking the camera on a tour around his room. It’s plastered with magazine covers and photos. 

MATT (ARCHIVAL): I got my Britney bag, Britney with a lollipop, the dolls, Britney style check, the valentines, got the new Britney magazine. 

TESS: Can you just paint us a picture of 14-year-old you? 

MATT: I was a sad, closeted gay boy, as most Britney Spears fans were at that time. BABS: Matt is all grown up now. 

MATT: Like every school dance, you know, they would play “Slave.” I would go out and dance in the middle of the floor. I ran for student council and I put Britney Spears posters

all over the school. Everything was Britney all the time. I didn’t -- OK, so also the crazy thing was I didn't allow myself to listen to any other music for three years besides Britney Spears. 

BABS (QUESTION): What was the first thing you listened to that wasn't Britney? Do you remember? 

MATT: I mean, like Madonna, you know. I was like, oh, Britney loves Madonna, Britney loves Janet. I gotta do what Britney does. 

BABS (TO MATT): And I think that there's nothing that can compare with that time of your life as far as, like, how obsessive you can be. It's just, wow, we really had all the time in the world to just do that. 

BABS: Instead of running around his neighborhood for MTV, Matt is now a staff writer for Buzzfeed. And even 18 years later, he’s still a huge Britney fan. He even links to that Fanography video in his Twitter bio. Though nothing can compare to the fervor he had as a teen. 

MATT: My religion was Britney Spears, so whatever Britney Spears said was my fact, was my Bible. Britney Spears drank Pepsi, I drank Pepsi. I hated Coke, even though we all know, looking back, that she, like, secretly loved Coke, I still was like, no, I only drink Pepsi now. 

TESS: Ah yes, Pepsi. Let’s take a quick Pepsi sidebar. In 2001, Britney signed on as Pepsi’s spokesperson -- a job that earned her 8 million dollars, and gave us moments like this iconic commercial. 

BRITNEY (SINGING): Ba ba ba ba, ba ba ba ba ba. The joy of Pepsi. 

TESS: Britney starts out in blue worker’s coveralls, and quickly sheds them to reveal her outfit: a white crop top, red suspenders, and ripped blue jeans. Yes, you can see her belly button ring, and yes, it’s a Pepsi symbol. She immediately bursts into dance, serving us peak Britney choreo. She hits every mark and then some. It’s sexy. It’s enthusiastic. It makes you thirsty. 

BRITNEY (SINGING): The joy of Pepsi, yeah. 

BABS: There’s something very organic about seeing Britney hawk a brand. She looks at home among the bright lights and the logos. I mean, Britney is a brand. She’s soda pop. She’s for sale. And kids like Matt were buying. 

MATT: Oh, I also wore Von Dutch at the time because Britney wore Von Dutch. Do you know - Britney wore to the VMAs the "page 666 shirt." And I was wearing that around my high school. And meanwhile, I'm like, you guys, “I'm straight. Britney's hot, you know, Britney’s hot,” like at the same time. It's like, jeez, the signs were there.

BABS: Matt is more than just a fan. He’s a stan. Part of “Britney’s Army” — that’s really what they call themselves. And this isn’t a small army… no. This is more like a full-on military sized operation. Trust us, we have read their blogs. We’ve relied on their tweets to track down hard-to-find archival tape of Britney. They treat Britney like a deity - literally, they call her Godney. 


BABS (QUESTION): Why do you think that the Britney Army is just so, like, hardcore? 

MATT: The thing about Britney army is that we grew up with her. We just were rooting for her because everyone was always not. You know? Like, everyone in the media. There was always something wrong with her, and everything that she did. And so I think that we saw, like, as fans, if you like, watched and followed her, you knew that her as a genuine person was smart, funny, just like, kind of a huge dork. My favorite Britney word is like “goob,” like I grew up saying “goob,” because she'd always be like “ah, I’m such a goob.” Just like this funny, she’s this funny dork, I think. And I think that we can identify with that. 

TESS: I’ve always loved Britney’s dorky side. She has a great snort laugh. She owns a T-shirt that says Talk Nerdy to Me. I also just love that she’s, like, basic. She loves Target. And yoga. Her celebrity crush is still Brad Pitt. To me, this core, relatable part of Britney is what sets her apart from other pop stars. 

BABS: And growing up in a super conservative Salt Lake City, I was in awe of her ability to own her sexuality. She danced in a way that would have gotten me banned from prom and maybe Utah in general. She wasn’t afraid to show off her body. And this was in a time when the president was on C-SPAN saying stuff like this. 

GEORGE W. BUSH (ARCHIVAL): We are headed in the right direction. But we still have work to do, so my administration is acting to encourage teens to make healthy choices. So we've requested a doubling of federal funding for abstinence-only education programs. 

BABS: At this time, purity culture was sweeping the nation. Everyone was talking about abstinence vows. Chastity rings were trendy, like they were low-rise jeans or something. America was spending a lot of time thinking about teens having sex. 

TESS: So, when Britney got a boyfriend, everyone tuned in. Around 1999, when Britney was 18 years old, she started dating one of the other most famous pop stars in the world - Justin Timberlake. They were like the Barbie and Ken of pop music. 


TESS: In 2000, both Justin AND Britney won “choice hottie” at the Teen Choice Awards.

BRITNEY (ARCHIVAL): Thank you for thinking I’m hot. 

TESS: Everyone knew they were dating at the time… but they got on stage together and pretended the thought had never crossed their minds. 

BRITNEY (ARCHIVAL): You are kinda hot, y’know. 

JUSTIN (ARCHIVAL): You know what, it’s funny, I was thinking the same thing about you, I mean I was thinking you were kinda hot too… 

BRITNEY (ARCHIVAL): We should go out! 

TESS: Perhaps their most memorable moment as a couple came at the 2001 American Music Awards, where Britney and Justin revolutionized both denim and the red carpet by arriving in coordinated jean formalwear. 

BABS: And I’d like to take a minute to shout out to all the men who’ve been forced into halloween couple costumes because of this. 

TESS: My husband included. [both laugh] 

BABS: The press was all over Britney & Justin’s relationship. But they didn’t exactly treat Britney and Justin the same. Justin would get questions about what it was like to perform live with his girlfriend. Britney would get questions like this: 

REPORTER (ARCHIVAL): I'm just wondering how you feel about the constant speculation about your virginity, and whether you are a virgin or not. 

BABS: Britney and the other female popstars of the era couldn’t avoid the pressure to not only be virgins, but to talk about it. To everyone. No matter how uncomfortable it made them. 

BRITNEY: I really wish I would have never said anything to begin with because I'm kind of stuck in this little place where people are always asking me. But, you know, that's just something that's part of growing up and that's just something that we all have to deal with. So. 

REPORTER (ARCHIVAL): Have there been any changes on that front? 

BRITNEY (ARCHIVAL): That's a personal question. 

BABS: Ew. Why were reporters asking a teenager about her sex life? And why was everyone laughing about it? 

TESS: And why weren’t any of the adults on Britney’s team intervening in moments like this? Like even a simple, “Hey, that’s inappropriate, next question.” Britney had this whole entourage.

She even had a manager that she’d been with since she was 13 - Larry Rudolph. He was very hands on with her career and image. He acted almost as a father figure to her. Where was he at all these press conferences? Why wasn’t he protecting her? We reached out to Larry Rudolph for comment, by the way. He didn’t get back to us. 

BABS: The reality is that this virginal image, it was lucrative for the Britney brand. Watching a teenager squirm at mature questions in a room full of reporters was good TV. And everyone was soaking it up. Even the kids. 

MATT (ARCHIVAL): Personally, I think Britney is still a virgin. She doesn't seem like the type of person who would do that kind of stuff because she came from a small town. 

MATT: I just can't like - MTV asked me, a 14 year old boy, if I thought she was a virgin, if her boobs were real. Also, my favorite part is they asked me if she was a virgin, and I said yes, because she's a Southern girl and wouldn't do “things like that.” TESS: [laughs] 

MATT: Like, the reason why I said that was because, you know what, Britney said she was a virgin, so I'm just going to repeat the same thing. Also, what is sex even, you know? 

BABS: The constant prodding and criticism of Britney was a call to action for the Britney Army. Soldiers like Matt reported for duty in lunchrooms across America. 

MATT: You would walk into school and you’d have Amanda over there being like, “oh, I don't like Britney, her boobs are fake.” And then you would have Becky in the corner being like, “oh, Britney's a slut.” And it would be like, what the what? So we grew up defending, we always were fighting for her, because people were always trying to beat her down. And we were always there kind of lifting her up. 

TESS: And never was that lift more needed than when Justin and Britney broke up. Just a year after the denim formal wear, the number one pop power couple had split in two. And everyone took a side. 

MATT (ARCHIVAL): The slimeball, Justin, dropped her on the ground just like that without giving it a chance. 

BABS: At 20 years old, Britney would go through her first big breakup in front of the entire world. 

TESS: Over the next couple years, her career continued to thrive. Glamour named her 2003’s “Woman of the Year.” She released her album “In the Zone” with hits like Everytime and Toxic, which she won a Grammy for. 


TESS: But eventually, the pressure to be that sexualized virgin who was not a girl, not yet a woman started to be too much. So Britney rebelled. 

JASON ALEXANDER: She invited me, just asking a friend to go to Vegas. We didn't plan on getting married. 

BABS: Next Time on Toxic: We talk to the guy who was married to Britney for 55 hours. 

JASON: It kind of like, was spur of the moment, and no one was happy and I was like oh shit this is about to get interesting.