The Prophet and the Poet: Tupac’s Humanity, Legacy, and Why His Words Still Heal Generations

For the longest time, until it just became too dirty for me to wear, I would wear my Tupac shirt whenever I had to run an errand or just take Yogi, our dog, out for a walk. I can’t find a picture of mine readily, but I’ll update this space once I find one of me wearing it.

I was not that courageous always in a way to show that I listened to his music or for that matter any hiphop music. For years, I was a “closet” hip-hop fan. I worried that those lyrics didn’t align with my dharma. I’d listen to 50 Cent or Usher, and tell myself that I was just listening to the music.

But as my boys started to grow up, I had to force myself to Google the lyrics and know what I was listening to. I’d find myself turning red as I finally understood what was being discussed, cue the “Anaconda” of Nicki Minaj, and so on.

But more about my hip-hop discovery journey later.

Recently, I found a letter from Tupac to Madonna, written while he was in prison on January 15, 1995. He was reconciling with her after initially breaking things off. While I’m not sure he ever meant for this to be made public, this communication is so self-aware and emotionally intelligent that it simply must be studied.

Tupac’s handwritten letter is full of heart and raw honesty that overshadows his menacing thug persona (I guess he didn’t have one, just that the genre of music he was into had that perception about it).

The effects of racism make it difficult for a young black male to properly show affection for an older white woman… For you to be seen with a black man wouldn’t in any way jeopardize your career, if anything it would make you seem that much more open & exciting. But for me at least in my previous perception I felt due to my “image” I would be letting down half of the people who made me what I thought I was.

This wasn’t about backstabbing, it was about self-preservation and a loyalty to the tribe that supported him. He felt the weight of representing a movement, and he feared that his personal happiness would compromise his professional credibility. 

What strikes me most is his capacity for change. Even behind bars and as he aged, he was evolving. He tells her,

I have grown both spiritually and mentally. It no longer matters how I’m perceived… Now my outlook is different everyone is judged and treated not by their color or fame but on how they treat me and because you have been so kind even in the midst of my craziness I offer my friendship once again this time much stronger & focused.

What breaks my heart is the haunting prophecy of his words. He was 25 when he was killed, and he speaks about the fragility of his life,

I felt compelled to tell you… just in case anything happened 2 me.

Imagine all the great things he would have done for the world beyond music, if only he had been given the gift of time.

Tupac’s lyrics feel like social commentary mixed with pure humanity. He rapped about poverty, racism, police brutality, and absent fathers. He sang to give voice to the marginalized, and in many ways, his words feel prophetic. He was fighting issues like mass incarceration and systemic inequality, and he died inflicted by it all.

His work has a full range of emotions, from the most tender to the most defiant.

In his poem, The Rose That Grew From Concrete, he writes,

Did you hear about the rose that grew from a crack in the concrete?
Proving nature’s laws wrong, it learned to walk without having feet.

And yet he would also go on to write a diss track challenging those who betrayed him, in Hit ‘Em Up,

Grab your Glocks when you see 2Pac
Call the cops when you see 2Pac, uh
Who shot me? But your punks didn’t finish
Now you ’bout to feel the wrath of a menace.

His early death cemented his legend status in my mind, but mostly, I am just sad. I’m sad about losing children to gun violence, and losing artists who have so much capability at such a young age. Tupac showed us the duality of our complex human lives. In his vulnerability, he showed he wasn’t afraid of his imperfections or his growth.

He taught us (mostly men, I hope) that softness is bravery.

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Observations, Opinions, and Cultural Critique

Cultural Essays from a Life Lived Between Worlds