Tupac Shakur

(Flow 10, Lyrics 7, Distinctiveness/Originality 11, Charisma 11, Consistency 8, Longevity 5, Punchlines 6, Subject Matter 9, Quality 9.5, Influence/Popularity 11)

It is impossible to be objective about 2Pac. He had the greatest voice, the greatest presence and the greatest charisma in the history of hip-hop. He is the single most popular individual in the history of rap music. He was such a giant that it was impossible to believe that he had been silenced by a handful of bullets, and like Bin Ladin, even seeing the autopsy photos just felt less than convincing.

You couldn’t kill Pac. He wouldn’t let you.

Even when he was dead, he was resurrected as a hologram. The Hollywood magic still felt more sincere than the innumerable rappers that tried to copy him and couldn’t. They didn’t have the intensity, the magic. They weren’t Pac.

It impossible to be objective about Pac. His work was a contradiction, a pastiche of every aspect of the rap genre, the swagger, the sadness. The lover and the fighter. The urban poet and the dreamer. He was a New Yorker that became the emblem of the West Coast. This quote kind of captures the toughness and sensitivity that was Pac:

“Number one, when I dis y’all..meaning like when you come up to me and I’m not giving you the type of reaction that you think I should give you, it’s not because I’m ungrateful… It’s because I’m nervous. I’m paranoid, I just got out of jail. I’ve been shot, cheated lied and framed and I just don’t know how to deal with so many people giving me that much affection. I never had that in my life. So if I do that ..don’t take it personal..Try to understand it and see it for what it is-“

It’s blasphemous to say it, but 2Pac was no lyricist. Pac used small, simple words to express complex thoughts, making him incredibly accessible, but not particularly lyrical. It was an intentional choice he made, which he credited to the small town directness of Marin City, California, where he lived at a key point in his youth.

Like everyone else on this list you think about what could have been. 2Pac was working on forming Death Row East. He had Eric B. He had Big Daddy Kane. Christopher Williams would do the hooks, and he was reaching out to the Wu-Tang Clan. He wanted to be a producer and an A&R label person. He wanted to make better, deeper music. He attended the Baltimore School for Performing Arts and enjoyed acting. Would it have worked? Who knows?

But what if?