This might be another entry a lot of hip-hop purists might suck their teeth at and Big Pun could arguably be the greatest emcee of all-time in a lot of people's eyes but, without an extreme mainstream presence, Big Pun has taken a huge leap backward landing at the 29th slot. The Terror Squad frontman was known not only for his complexly insane bars but also for his presence in the streets. Big Pun was a true street dude who happened to be extremely nice at rapping.
Many forget that Big Pun appeared as a guest feature on Fat Joe's 1995 album, Jealous One's Envy but, later became the lead rapper of his clique after quickly developing one of the best flows in hip-hop to this date. His popular single, 'Still Not A Player' gets club play to this day and his 1997 album, Capital Punishment is a certified classic amongst most rap fans.