14. Alan Jackson, 'Freight Train'
Jackson’s albums don’t always fly off the shelves—“Like Red on a Rose,” his moody 2006 collaboration with Alison Krauss, was only a modest success, selling around 500,000 copies—but when he’s in his wheelhouse, no country star this side of Keith Urban is more of a lock to move millions of units. Until, that is, he released "Freight Train," which has stalled at just over 200,000 copies sold, despite being no more or less sturdy than any of his 15 previous albums. The lack of a hit single (both “It’s Just That Way” and “Hard Hat and a Hammer” failed to crack the Hot Country Songs Top 10) surely didn’t help—but still, this is one flop that has us (and probably the folks at Arista Nashville, Jackson’s label) scratching our heads.