42. Willow Smith
The 11-year-old daughter of Will Smith and Jada Pinkett Smith struck gold with the massive party anthem “Whip My Hair.” But the pint-sized mini-diva’s second single, “21st Century Girl,” fell flat, peaking at No. 99, and her Nicki Minaj-aided follow-up “Fireball” failed to chart at all. Perhaps not coincidentally, the release of her debut album, "Knees and Elbows," has been pushed back several times. However, with mentors like Jay-Z on her side, Smith has all the wisdom (and time) in the world to grow her career.—Jeff Royer
(Photo: Frederick M. Brown, Getty Images)
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