“If you were talking to your little sister [Jamie Lynn Spears] now, and the girl who said she was gonna stay a virgin until she got married,” Sawyer says. “Do you still think there’s something to be said for that?” For context, Jamie Lynn was 12 when this interview aired.
The inquisitions don’t stop there. “What happened to your clothes?” Sawyer asks Spears at one point, holding up photos of Spears’s nearly-naked magazine covers. “What is it about?”
But Spears is unapologetic. “What is it about? It’s about doing a beautiful picture. I feel comfortable in my skin,” she says. “I think it’s an okay thing to express yourself.”
Still, Sawyer presses on. “Have you ever gone further than you wish you had?” she asks, to which Spears says, “Gone further? No.” It’s only when Sawyer pointedly pesters Spears with a specific image that Spears changes her answer.
In what now feels like a, “Gotcha!” moment, Sawyer pulls out images from a particular semi-nude photo shoot in which Spears is wearing nothing but pearls. “OK, those are a little much,” Spears relents, saying she felt “weird” about the shots. “Wish you hadn’t done it?” Sawyer asks. “A little bit,” Spears replies.
Later in the interview, as Framing Britney Spears shows, Sawyer tells Spears about something Kendall Ehrlich, the wife of Maryland’s former governor (Robert Ehrlich), said: “Really, if I had an opportunity to shoot Britney Spears I think I would.”
“Oh, that’s horrible,” Spears says. Sawyer muses in response, “Because of the example for kids and how hard it is to be a parent and keep all of this away from your kids.”
“Well, that’s really sad that she said that,” Spears says, doubling down. Yes, it is. (Thankfully, Spears doesn’t give in, shooting back, “I’m not here to babysit her kids.”)