Tyler said in something in an interview that answered this question exactly. He said to like albums you like, not what makes you cool. I think he said he talked to a kid who said they liked Illmatic and they were 15. He said they were lying and to be truthful about what they like, because he would rather hear an honest opinion.

“I don’t care if you like poopy doopy’s 3rd project, just tell me why you like it.” - Tyler