9. "These Boots Are Made For Walkin'"
Frank Sinatra's daughter Nancy scored a number one hit in 1966 about using her favorite footwear to trample on her loser boyfriend. Jessica Simpson chose to sing the same track for the soundtrack of The Dukes of Hazzard (a movie remake in which she co-starred), and even released a raunchy music video to display her then-toned physique. Sadly, her wheezy singing and lame rapping were anything but sexy.
Nancy Sinatra:
Jessica Simpson:



