Seth Poppel, Yearbook library
In this guessing game, The BoomBox gives you three hints about the singer pictured, then click the button below and see if your pop culture knowledge is on point.
-- This Bronx, N.Y., native had success as dancer and actress before releasing her debut album, named for the subway line she rode growing up.
-- Her "big break" came in 1991, when she was hired as a background dancer for New Kids on the Block on the American Music Awards.
-- No stranger to public breakups, this quadruple threat -- singer, dancer, actress and reality TV star -- famously dated a record producer, nearly married a Hollywood heartthrob and walked down the aisle with a fellow singer, though they recently announced their separation.
And to see other music stars and celebs before they were famous, click over to Snakkle!