5 is a really small number to narrow it down to....
1) Tupac. There's really no contest to me here. No other rapper can tell a story as well as he could. Nor does any other rapper have the charisma to cross over race and gender boundaries like he did.
2) A Tribe Called Quest. Individually...Meh. But together they helped create the foundation for hip-hop culture.
3) De La Soul. Best authentic Hip Hop live show you will ever go to, even now. I saw them back in 2010 and they were great.
4) Talib Kewli & Mos Def. At their best as Black Star but each could hold their own as a solo artist as well. Saw them live in 2011... not bad, but no where near as good as De La Soul.
5) Joell Ortiz - this is a personal preference. Probably not really top 5 all time (prob not even top 25), but consistently underrated. Really funny lyricist.
Over favs - Notorious BIG, Wale, Outkasts, The Roots, Mobb Deep, Little Brother, Slum Village, Wu-Tang, J-Live, Akrobatic, Guru, Eric B and Rakim... too many to list. Been listening to Hip-Hop since the mid 80s.
If you guys like Hip-Hop music (more specifically east coast) then you should check out TTTradio.net. They do a live show every friday night with multiple DJs across the country. Great show on from around 6pm-11pm depending on the DJs playing. You'll hear a lot of classic 90s stuff and some new ones too. I honestly listen to downloaded mixtapes from these guys more than anything else. best way to get a great variety.
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