Britney Spears' personal life has attracted considerable media attention. Some people feel that she has courted it by cultivating, in her early years at least, a chaste, God-fearing and "wholesome" image. It was somewhat at odds, not only with the traditional pressures, temptations and opportunities of "pop 'n' roll," but with the increasingly sexualized content of her own image and songs. Spears' kiss with Madonna at the 2003 MTV Video Music Awards received much media attention, as have her romantic relationships.

It began in April 1999 when a then 17 year-old Spears was featured on the cover of Rolling Stone[38] magazine in a sexually suggestive Lolita-themed photo shoot which triggered widespread speculation (denied by her representatives) that the singer had opted to have breast implants.

In August 2003 the artist reached more controversy with a photoshoot by photographer Michael Thompson which appeared on W Magazine. The photos display Britney in a heavy dominatrix inspired shoot, and sexually suggestive poses. In the interview by Rob Haskell which accompanied the photos, Spears admitted to having lost her virginity to Justin Timberlake two years into their relationship. She also stated that she in fact smokes, and she did kiss Colin Farrell but had no relationship with him. [39]

The sexualized public image of Spears once again became a topic of debate as a result of her November 2003 semi-nude photo spread for the men's magazine, Esquire. Prompted by this, Playboy reportedly offered the star over one million USD to pose nude for their magazine, but Spears publicly declined.[40] In an interview with Diane Sawyer, she was asked if she had ever gone further than she wished she had with the sexualized photo shoots. Spears responded, "No, I don't think so, no." After the Esquire photos were held up in front of her, she said, "Okay. Now those are a little much. Yeah, those are a little much. That's one picture, I must say, that I felt kind of weird about, yeah."