One thing most intense music fans agree on nowadays is that the mainstream sucks. That's probably a sentiment that's always been true among the underground, but you even hear it among casual listeners today. "I don't buy albums because only one or two songs are going to be good" is a common refrain.
Photo by Groovehouse Les Claypool of Primus
One of the reasons for this is that most pop music is highly manufactured and highly generic. Pop stars are rarely famous by accident, and few of them today are the kinds of artists who dabble in experimental or avant-garde music. That's all well and good, but there's a reason popular music was once so innovative: musicians like this used to occasionally break into the pop world. Here's five who did it successfully.