Originally Posted by monthh
Try Rakim, Nas, Common, 2Pac, A Tribe Called Quest, Biggie, LL Cool J, GangStarr, Lupe Fiasco, Pete Rock and C.L. Smooth, The Lox, Jay-Z, and Run DMC to start with for a good, easy to find, cross-section of Hip Hop. Then move on to some other all time greats like Talib Kweli, Mos Def, Blackstar, The Roots, Big L, Big Pun, Eminem, Scarface, and Wu Tang Clan to expand your knowledge. After you listen to these people you will naturally find the people these guys are related to such as Jean Grae, Pharoahe Monch, Fat Joe, 50 Cent, Young Jeezy, Kool G Rap, Big Daddy Kane, Dr. Dre, Snoop, Redman, Jay Dee, Madlib, MF Doom, and so on. You should then be able to figure out what kind of rap you like, and branch out to find even more artists.
Also, you should try to find whole albums, and not just individual songs. Good rappers can put whole albums together, while any rapper can put out a couple good singles.
I just re-read your original post, and you said original Hip Hop, so I would say go for early LL Cool J, Slick Rick, Rakim, Busy Bee, Doug E. Fresh, MC Shan, Kool Keith, KRS One/Boogie Down Productions, Beastie Boys, Run DMC, Public Enemy, The Roots, Ice T, NWA, OutKast, A Tribe Called Quest, Arrested Development, Queen Latifah, Will Smith/Jazzy Jeff, De La Soul, and maybe some like Too Short or E-40 if you want to listen to rappers that were pioneers or do their own thing/sound a little different.