Macy Gray
With her hit "I Try," the former Natalie Renee McIntyre raspily crooned her way to the top of the charts - paving the way for female pop-jazz stars such as Amy Winehouse and Adele. She hit pay dirt once again in 2003 with "I See You," but spent the remainder of the decade mostly appearing in small movie roles and on the odd soundtrack. After a failed attempt to rebrand herself as Nemesis Jaxson, Gray returned briefly to the spotlight as a contestant on last season's Dancing with the Stars. Sadly, she was the second participant to be eliminated, but at least she tried.