97. Darius Rucker, "Wagon Wheel"
With a vocal assist from Lady Antebellum, the former Hootie and the Blowfish frontman-turned-country singer covers the Old Crow Medicine Show signature tune – which is in fact a reworked Dylan outtake circa Pat Garrett and Billy the Kid. Result: a left-field country Number One. Now how about "Lay Lady Lay," dude?