An admission at the outset: these aren't the five worst rap lyrics of all time. This list consists of mostly well-known, primarily well-respected hip hop artists. The thing is, we don't listen to bad rap, and neither should you. Bad rap is, like, really bad, and there's TONS of it.
Also, we aren't ranking the dumbest hip-hop lyrics ever. That would be like making a list of people Hitler was mean to. There have been 6 million lyrics across the brief history of rap so dumb that they should be punishable as crimes against humanity. Sometimes rap lyrics are so dumb they're ingenious, and we love those lyrics like a fat kid loves cake.
So what criteria are we using to judge these lyrics? That will be explained as we examine each of the offending phrases. For now, let's just acknowledge that there is an unspoken contract between rappers and their listeners, which boils down to this: "While I'm listening to rap, I want to feel like we are both cool and like we are both bulletproof. Don't say anything that's going to f**k up either of those illusions for me." The following lyrics from some of our favorite rappers, embedded as MP3s below (the little black bars), violated that contract in spectacular fashion.
Fool me once ...
You can't take it with you. So, they didn't.
A lot of medical problems read like horror movie scripts.
These guys make the Joker look like a well-adjusted citizen.