Shelby Lynne (2000)
Another country singer got the nod over Brad Paisley? Strange but true. Shelby Lynne was the type of underdog Grammy voters love to root for — an edgy singer-songwriter who'd paid some dues. She had the country cred, the whiskey-slugging outlaw image, the juicy backstory. What she didn't have was any more hits. She proved she didn’t need them, though, with projects like her 2008 album of Dusty Springfield covers Just A Little Lovin'.