It seems like when young female pop stars first burst onto the scene with their sweet, “I have a crush on you” type songs, it’s only a matter of time before they go to the dark side. Or should we say the sexy side. Carly Rae Jepsen got her start with her innocent Call Me Maybe and now the 27-year-old (!!) is trying out her seductive side with her latest music video for Curiosity.

From Britney Spears to Jewel, most women in the industry have tried “sexy,” but not all of them could pull it off. In this week’s My Monday Playlist, here are some of the most memorable – or just uncomfortable – attempts at sweet pop stars gone sexy.

Carly Rae Jepsen – Curiosity

Verdict: It seems like Carly is dipping her toes in the sexy pool with this one, but she definitely made it work. Win.

Britney Spears – Don’t Let Me Be the Last to Know

Verdict: Sure, …Baby One More Time got people talking about Britney, but this one showed off her sexy side in a whole new way. But it worked for her! Win.

Miley Cyrus – Can’t Be Tamed

Verdict: Where’d Hannah Montana go? While we believe that Miley really can’t be tamed (and we know that now) at the time the feathers and the cage was just too much. Lose.

Jewel – Intuition

Verdict: Remember when Jewel tried to be sexy? Yeah, most of us try to block it from our minds. Lose.

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Christina Aguilera – Dirrty

Verdict: Christina was always “on the fence” with her sexiness, but Dirrty took it to a whole new, raunchy level. Plus, this phase of piercings and black streaks didn’t last long. Lose.

Nelly Furtado – Promiscuous

Verdict: Bringing in Timberland is one way to prove to everyone that you’re really not Like a Bird anymore. Nelly made this work for her. Win.

Jessica Simpson – Irresistible

Verdict: Poor Jessica. She had to compete with THE Britney Spears and Christina Aguilera during the early 2000’s as another blonde pop star. Wearing a leather outfit and having wind blow through your hair while singing seductively into the camera caught some attention.

Charlotte Church – Call My Name

Verdict: Goodbye long gowns and gospel songs! Honestly, this is just uncomfortable to watch. And what’s with the “hanging upside down” scene? Lose.

Who’s your favorite pop star gone bad and who just couldn’t make it work?