Era of Prominence: Late 1990s-early 2000s

Sure, Jay wore regular durags, as many rappers did at the time. But let's be honest, his T-shirts as durags were far more interesting (positive or not, take it how you will). Some even say he was responsible for popularizing the look. Whether or not you agree with that statement or the trend itself, you can't deny the fact that this Hov once existed. And if it weren't for him (and a few other rappers), there would be no YouTube videos about how to wrap a shirt on your head, or step-by-step instructions on eHow