76. Nelly Furtado
Age (circa 2009): 30
She dipped in and out of the spotlight during the Aughts, but this cool Canadian chick always made a lasting impression with her unique voice and impeccable looks. Judging from her most recent public appearance, we've got another name to add to the MILF list.
Resurrecting Timbaland's career with her stellar 2006 album Loose.