Fiery and fun, aspiring country artist Jo Dee Messina befriended a record executive backstage at one of her friend Tim McGraw's shows and subsequently burst onto the music scene in '96 with her energetic, self-titled debut album. While some of the singer/songwriter's biggest hits have a headstrong and confident edge, Messina has also touched fans with her poignant ballads. After satisfying a 17-year contract with her label, the Massachusetts-born star fully financed her '14 album, Me, with crowdfunding, proving the loyalty of her adoring fanbase.