9. Jessica Simpson - "These Boots Are Made For Walkin'"
For an extremely brief period in the mid-2000s, Jessica Simpson was sort of a movie star. Her most famous role is Daisy Duke in the Dukes of Hazzard movie. Willie Nelson, Stifler and Johnny Knoxville all acted circles around her, the movie bombed and pretty soon she was making straight-to-DVD dreck like Private Valentine: Blonde & Dangerous. Anyway, she recorded Nancy Sinatra's 1966 classic "These Boots Are Made For Walkin'" for the Dukes soundtrack. She looks great in the Brett Ratner-directed video and purred like Britney Spears throughout the song, but even a Willie Nelson vocal cameo couldn't make the track anything but an embarrassment.