First Hit #1: February 26, 1966
It’s strange to watch the video for this song, as audio alone it makes Nancy Sinatra seem frighteningly sexy, while the video itself reveals her to be more charming and cute. The distinctive descending notes at the beginning set it up, and then Sinatra keeps a slightly menacing tone throughout. She sounds scary, but scary in an arousing way. It’s possibly the sexiest song that has been a hit so far, which is an odd thing to say about a song that is pretty much about the dangers of cheating on Nancy Sinatra.
Another interesting thing is that it’s a deceptively simple song, but really easy to screw up. Jessica Simpson demonstrated this in her cover, which brings in some overt sexuality that makes it less arousing, and extra instrumentation and a modern beat that serve to dilute the power of the track. As originally performed, it’s the most uncomfortably sexy pop song of all time. As covered by Ms. Simpson, it’s a boring pop song with some bad country overtones. By bringing the sex, ironically, Simpson removes it completely. Sinatra and Lee Hazelwood knew that you don’t have to be overtly sexual, you just have to get the mood right and a slight tease does more than throwing it all out there.
The terrible cover, for comparison: