Citing Jackson's resolve to incorporate personal and social issues into her work and Madonna's ability to constantly redefine the boundaries of socially acceptable material in the industry, Spears's catalog ultimately pales in comparison, because "while Jackson and Madonna wrote their own music about subjects of importance, Spears's music sounds like an upbeat version of either, 'I want to grow up but the media won't let me,' or 'Here kitty, kitty, I'm wearing my underwear outside of my leather pants'-type ballads." In contrast, Guy Blackman argues that although "no one would argue that Spears is some kind of pioneering pop auteur, there’s still a lot to like about her back catalogue. During her world-conquering peak, she was just about as cutting edge as you could get in the world of global pop superstardom. Spears didn’t just work with big names, she gave big names their names, and maintained her high currency in the world’s most fickle industry for years, when most aspiring starlets are lucky to manage months."
After meeting Spears face to face, Janet Jackson stated: "she said to me, 'I'm such a big fan; I really admire you.' That's so flattering. Everyone gets inspiration from some place. And it's awesome to see someone else coming up who's dancing and singing, and seeing how all these kids relate to her. A lot of people put it down, but what she does is a positive thing." Madonna's respect for Spears has also been a subject of observation. Santiago Fouz-Hernández and Freya Jarman-Ivens, authors of Madonna's drowned worlds: new approaches to her cultural transformations, 1983-2003 (2004) note that the most well known cross-generational relationship exists between Spears and Madonna in which "the entertainment newsmedia almost became obsessed with their relationship of mutual admiration." The biographers also report "some observers of popular culture, however, feel that the comparisons between the two artist are meaningless and fail to recognize Madonna's unique contribution: Madonna was never 'just another pop star' whereas Britney can more easily be seen as a standard manufactured pop act."