Tyrphanax said:
KRS-One, Ghetto Boyz, Busta Rhymes, and House of Pain are pretty great. Gotta get some Kurtis Blow and Afrika Bambaataa and the Zulu Nation in there, too, though. Snoop and Dre and Ice Cube as well. Bel Biv Devoe? <_<
Generally for "newer" stuff I go for guys like Ludacris, Wildchild, Madlib/Quasimoto, Heiroglyphics, Deltron 3030/Del the Funky Homosapien, Jurassic 5, Dr. Octagynecologist/Kool Keith, Lootpack, Wu-Tang Clan... I also admit to a soft spot for Kanye West and DMX.
I'm sure there's more than that, but that's all that are coming to me. I love the underground stuff, it's just way better than the popular rap/hip-hop they put on the radio.
Hmm... Hit and miss. Definitely J5, Del/Deltron, Hiero, KRS, Keith.
Also check these out if you haven't already: A Tribe Called Quest, Mos Def, Abdominal/Format, Blackalicious, Lyrics Born, Quannum, Mighty Underdogs, Chali 2na, Panacea, Binary Star, DJ Shadow :)
RE Will Smith - he was quite a talented lyricist but his skills were average compared to those of DJ Jazzy Jeff. Unfortunately their most well known songs were just a platform for Smith's ridiculous story raps. I also don't rate anything made after their first 3 albums; they started relying on repetitive hooks and lame r&b sounding shite.*
Listen to The Magnificent Jazzy Jeff for a showcase of Jazzy's skill, including his "Transformer scratch" from their 1989 debut album made while the pair were still in high school. The songs with "Jeff" in the title are the best ;)
* I tell a lie, Who Stole the DJ? is pretty good.