There comes a time when every teen boy bander or male popstar turns from innocent heartthrob to promiscuous adult — and they make a whole album to let you know about it.

This phenomenon all started when Justin Timberlake traded the N*SYNC’s teen pop bangers for the sensual R&B tunes on his debut solo record Justified (2002) – ultimately distancing himself from the fangirl stigma to be taken seriously by an older, male demographic.

After Timberlake, this phenomenon was repeated by others like Jesse McCartney, Nick Jonas, Justin Bieber, Zayn Malik, and Liam Payne. We’re ranking each of their transitions from the cringiest of bad boy rebrandings to the suavest.

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Boys to Men: When Heartthrobs Split From Their Teen Pop Image