Tupac Shakur [music]

Calvin

Welcome to Headstones and Microphones where we use AI to step into the past through a researched, first-person simulation of history's most interesting people. I am your host, Calvin. While we’ve added some creative storytelling, our goal is to inspire your own study of these fascinating lives. Now, let’s meet our guest. Today we are joined by one of the most influential voices in music and culture, a poet, an actor, and a revolutionary. Welcome to the show! For those who may somehow not know who you are... who are you?

Black Male

Thank you so much for having me, man! It is a blessing to be back in the mix and sharing my heart again. My name is Tupac Amaru Shakur, but most people just know me as 2Pac or Makaveli. I’m a soul that tried to use words to paint the reality of what we were seeing in the streets—the struggle, the beauty, and the hope.

Calvin

It’s truly an honor. Let’s take it back to the very beginning. When and where were you born?

Black Male

I was born on June 16, 1971, right in the heart of East Harlem, New York.

Calvin

And what was your given name at birth?

Black Male

My mother originally named me Lesane Parish Crooks.

Calvin

That’s a name a lot of people might not recognize! Is there a story behind your name changing to Tupac?

Black Male

Definitely. My mother, Afeni Shakur, wanted me to have a name that carried weight and history. She renamed me Tupac Amaru after a revolutionary Inca chief who led a rebellion against the Spanish. It means "shining serpent." She wanted me to know that I came from a line of fighters and people who stood up for what they believed in.

Calvin

What was your hometown like growing up?

Black Male

Growing up in Harlem and later the Bronx, it was vibrant but tough, you know? There was music and life everywhere, but there was also a lot of poverty and struggle. When we moved to Baltimore, Maryland, things shifted for me because I got into the arts. Baltimore felt like a place where I could breathe and actually see a future in my creativity.

Calvin

What was your family life like?

Black Male

It was intense. My mother was a member of the Black Panthers, so I grew up with a very strong political consciousness. We didn't have much money—we moved around a lot, often living in shelters—but my house was always filled with deep conversation and the spirit of revolution. My mother was my hero; she taught me how to think for myself even when the world tried to tell me who I was.

Calvin

What kind of kid were you?

Black Male

I was a bit of a "nerdy" kid, to be honest! I wasn't out there playing basketball like everyone else. I was inside writing poetry, reading books, and watching a lot of TV. I was very sensitive and spent a lot of time in my own head, just observing everything around me.

Calvin

What were your biggest fears growing up?

Black Male

My biggest fear was just being ordinary or not being able to take care of my mother. I saw how hard she worked and the battles she fought, and I feared that I wouldn't be strong enough to change our situation.

Calvin

What did you dream of becoming as a child?

Black Male

I wanted to be an actor and a performer. I loved the stage. I felt like I could be anyone when I was acting.

Calvin

What were some of your favorite activities in school?

Black Male

Oh, definitely the drama department and poetry. When I got to the Baltimore School for the Arts, I was in heaven. I was performing Shakespeare and even played the Mouse King in The Nutcracker! That school was where I realized that my voice had power.

Calvin

What was your first job?

Black Male

My first real break into the business was working as a roadie and a backup dancer for the group Digital Underground. I was the guy carrying the equipment and keeping the energy up on stage before I ever got to touch a microphone.

Calvin

Was there a moment where you realized you were different from everyone else?

Black Male

It was probably during those Shakespeare classes. I’d look around and see that I was connecting with these old stories in a way that felt modern. I realized I could bridge the gap between the street and the stage. I knew I had a mission that was bigger than just making songs.

Calvin

What’s a decision that changed everything for you, but felt small at the time?

Black Male

Joining Leila Steinberg’s poetry class when I moved to California. It seemed like just another way to pass the time, but she became my first manager and really pushed me to take my music seriously. That one class set the whole domino effect in motion.

Calvin

What was your biggest break?

Black Male

Getting my verse on the Digital Underground track "Same Song." That was the first time the world really heard me. After that, everything moved so fast.

Calvin

What were your biggest struggles before success?

Black Male

Just the basic stuff—hunger, not knowing where we were going to sleep, and feeling like no one was listening. Dealing with the law was a constant shadow too, even before the fame.

Calvin

Did you ever consider quitting?

Black Male

Never. I felt like if I quit, I was letting down everyone who didn't have a voice. I had too much to say to ever stay quiet.

Calvin

Were there any specific daily habits or routines that you feel are essential to your success?

Black Male

I was a workhorse. I would stay in the studio for days, recording three or four songs a night. My routine was basically: write, record, repeat. I felt like I was in a race against time, so I never wanted to waste a second. I also made sure to keep reading. You can't put out good words if you aren't taking in knowledge.

Calvin

What job would you have had if fame never happened?

Black Male

I think I would have been a teacher or maybe a lawyer. Something where I could fight for people and use my words to change things.

Calvin

What was your life like before fame?

Black Male

It was a lot of dreaming and a lot of struggle. I spent a lot of time on the bus, writing lyrics on napkins and notebooks, just hoping for a chance to show the world what I could do.

Calvin

How did relationships change after success?

Black Male

It gets complicated. You start to wonder who is there for you and who is there for the "2Pac" persona. It makes your circle smaller, but it makes the real connections you do have feel a lot more important.

Calvin

Did fame bring happiness?

Black Male

It brought the ability to take care of my family, which was my biggest goal. But happiness? That’s something you have to find inside yourself. Fame is just a spotlight; it doesn't change what’s happening in the dark.

Calvin

What was the downside of becoming famous?

Black Male

The lack of privacy and the way people try to box you in. Everyone wants a piece of you, and everyone thinks they know your story better than you do. It can be very lonely in the middle of a crowd.

Calvin

What misconceptions did people have about you?

Black Male

People thought I was just this angry, violent guy. They didn't see the kid who loved Shakespeare or the man who wanted to start programs for the youth. They saw the "Thug Life" tattoo but didn't understand the philosophy behind it—that it was about the underdog rising up.

Calvin

What’s something people misunderstood about your life?

Black Male

That everything I did was for a reaction. Most of what I did was because I felt it in my soul. I was a very emotional person, and I led with my heart, even when it got me into trouble.

Calvin

Tell me about a time when everything went wrong and how did you handle it?

Black Male

There were many times, but I always lived by the idea that through every dark night, there’s a bright day. I’d just stick my chest out, keep my head up, and handle it. You can't let the weight of the world crush you.

Calvin

Who had the biggest influence on your life?

Black Male

My mother, Afeni, without a doubt. She was the one who gave me my mind and my spirit.

Calvin

What were you working on in your career before you passed away?

Black Male

I was recording music constantly—I had so much material in the vault. I was also getting deeper into acting and looking at scripts that would challenge me. I wanted to move into producing and directing, too.

Calvin

When and where and how did you pass away and how old were you?

Black Male

I passed away on September 13, 1996, in Las Vegas. I was only 25 years old.

Calvin

What’s a random fact about you most people have never heard?

Black Male

I actually auditioned for the role of Bubba in Forrest Gump! I didn't get the part, but I always thought that would have been a wild role to play.

Calvin

What was your favorite food?

Black Male

Fried chicken wings with plenty of hot sauce and a big side of macaroni and cheese. And you had to wash it down with a Sunkist orange soda!

Calvin

What was your favorite book?

Black Male

I loved The Catcher in the Rye. I felt a real connection to Holden Caulfield and that feeling of being an outsider looking in.

Calvin

What’s your funniest behind-the-scenes moment?

Black Male

Just clowning around on the set of music videos. When we were filming "How Do U Want It," we were just having a blast, laughing and joking the whole time. People see the serious side of me, but I loved to laugh and have a good time with my friends.

Calvin

What advice would you give people chasing success?

Black Male

Don't stop dreaming. Reality is often wrong; dreams are what's real. You have to be willing to pay the price to make them come true. And always, always keep your head up.

Calvin

This has been incredible. Do you have any closing remarks about the interview or the stories you shared that you would like to share with the listeners before we sign off?

Black Male

I just want to say thank you for listening to my story. Life is short, so make sure you do as much as you can and help as many people as you can before it's your turn to leave the game. Stay true to yourself and never let your spark go out. Thanks for having me, Calvin. It’s been a beautiful time.

Calvin

Thank you, Tupac. What an amazing look into the life of a true legend. From the Shakespearean beginnings to the heights of global fame, your voice still resonates today. And that wraps up another conversation from beyond the grave. Thanks for joining us on The Headstones and Microphones Podcast. Remember—legends may die, but their stories never do. Please help spread the word by sharing and following the pod.