"These boots are made for walking, and that's just what they'll do, one of these days these boots are gonna walk all over you."
Easily the most passive-aggressive song on the list, "These Boots Are Made For Walkin'" was released in February 1966 and shot to No. 1. The song has been adopted as a rallying cry for everything from pulling out of Vietnam to the introduction of the Fembots in Austin Powers.
Nancy Sinatra was reportedly told by Lee Hazlewood, the song's writer and producer, to sing it as if she was a 16-year-old girl brushing off a 40-year-old man. Hazelwood presumably followed that creepy request up with, "Not that I know what that sounds like."
That was apparently an era when 16-year-olds could brush off a dirty old man with a few melodic words about how she had found an even more experienced lover ("And what he knows, you ain't had time to learn ..."). Today, she'd have to change her address, her cell phone number, get all new MySpace friends, and call To Catch A Predator.
Bitterness level: 4
Nobody ever said the Sinatra's were great actors. The lyrics may be bitter, but her voice and the performance in the original video suggest less enraged woman and more of a "I'll keep the boots on while we have sex if you'd like me to" vibe.