ALI CALDWELL, 28 (9-10AM eastern) (Team Miley)
Woodbridge, NJ
Ali skipped college to join Xhale, a three-person R&B group. They opened for Boys II Men and played for Patti LaBelle at her tribute concert. Although they met with several record labels, they couldn't get signed and called it quits in 2010. In 2014, Ali went to Russia and toured all over the country with a successful jazz musician named Oleg. Since then, she has been to Russia five times and performs more than 20 shows a year.