8. Justin Timberlake
The second biggest boy band of the late 90’s, N’Sync, always had a clear front runner for potential solo artist, and everyone knew it was Justin Timberlake. During the band’s hiatus, Timberlake released his debut solo album Justified in 2002 which included the singles “Cry Me a River”, and “Rock Your Body”. He earned his first two Grammy Awards (of an eventual nine) as a solo artist. He went on to release three more albums, appear in various movies, and even win a couple Emmy’s for his work on Saturday Night Live sketches, like fan favorite opposite Andy Samberg, “Dick in a Box”. Say the name Justin Timberlake now, and hardly anyone even remembers he started out in a boy band.
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