As I was searching, I discovered that Owsley is actually part of a large cluster of extremely poor Eastern Kentucky counties. In fact, according to Wikipedia, of the 100 poorest counties in the US by median household income, 16 are in this region of Eastern Kentucky. So I looked at the 2008 voting returns in those 16 counties. Remember, these are counties where probably around half of the residents depend for survival on food stamp appropriations (not to mention Medicaid, TANF, etc.).
Clay - 78-21 M McCreary - 75-23 M Wolfe - 50-47 O Leslie - 81-17 M Martin - 77-22 M Knox - 72-27 M Magoffin - 52-45 M Jackson - 84-14 M Owsley - 76-23 M Breathitt - 53-44 M Knott - 53-45 M Menifee - 51-46 O Bell - 70-29 M Harlan - 72-26 M Letcher - 65-32 M Lawrence - 62-36 M