You honestly can't give shit about him liking Lil' Wayne if you put Biggie. Biggie is EASILY the most overrated rapper of all time (Lil' Wayne for a close second).
I hate these types of questions because most people ALWAYS go with the most stereotypical answers: Biggie and 2pac. I'm actually surprised I didn't see that more in this thread. 2pac was pretty good, but Biggie was absolute garbage. Pretty much my exact thoughts on Bigge:
I mean...come on...the guy rhymes "thirsty" with "day". Big L SHITS on Biggie; no 'ifs' 'ands' or 'buts'.
As far as a lengthy, musical career goes, I'd have to give it to Jay-Z, Nas, and Ice Cube. While I'm not really huge fans of any of these guys, I respect how long they've been in the game successfully. Jay Z doesn't even write his music down; he writes key notes and goes into the studio and raps what's on his head.
As far as personal preference, I'd have to give it to Eminem. No other rapper can keep me as entertained in a song as much as Eminem can. Close 2nd is Taj-He-Spitz; have to give it up to an underground Cali rapper.
Some songs by mentioned artists:
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