During Tupac Shakur’s very brief, yet immensely impactful life, he accumulated an innumerable amount of supporters, as well as an interesting list of celebrity friends; everyone from Madonna and Mickey Rourke to Jasmine Guy and Jada Pinkett Smith had some sort of relationship with the beloved rap legend.

But arguably the most shocking friendship he acquired was with actor Tony Danza. Known for his roles on hit TV shows like Taxi and Who’s the Boss, Danza befriended ’Pac in 1995 via mail, when ’Pac was serving a one-and-a-half to four-year sentence for a sexual assault conviction (of which he only served 11 months). The former boxer-turned-thespian surprisingly reached out to Shakur in a moment of need and an unexpected relationship was formed.


XXL recently chopped it up with Tony to find out what exactly they spoke about while pen pals and why he felt compelled to contact ’Pac in the first place. As the theme to Who’s the Boss goes, “There’s more to life than what you’re livin’.” —Jesse Gissen

XXLMag.com: I don’t know if you’re aware but we’re approaching the 15-year anniversary of Tupac’s death this month.

Tony Danza: That’s unbelievable.

It really is. You corresponded with him while he was in jail in 1995. How did that begin? What motivated you to write a letter to ’Pac?

First of all, I’m a fan. I’m just a fan. I was a fan of his—and I’ll be honest with you, I’m not the biggest fan of gangster rap. But I was a fan of his, and the phenomenon really interested me, you know. And then, when he got shot five times, and then they had the sexual attack on that make-up lady, or something, I don’t remember what the deal was. He goes to jail. So I’m in my car one day, hitting the button and I hit “Dear Mama.” I hear his song, and I just thought to my self, "jeez, it’s really interesting that this guy that wrote this song is sitting in jail, with five bullet holes, with a big sign that says 'Thug Life' tattooed on his stomach, and yet here he is writing this kind of music, and doing this kind of work—pretty good actor too." So, I just like to write people, because you’re somebody, they write back. It’s interesting; I think people write back for the most part anyway ’cause, getting a correspondence is so rare.

What exactly did the letter say?

So I wrote a note to him—a letter to him, and I said “Hey Tupac,” and it was so weird, I’ll never forget, I was trying to think, "what do you write? Do you write Tupac? How do you do it? 'Dear Tupac?' I don’t know—'dear [the number 2-Pac]?' I don’t know." So anyway, I just wrote and said “Listen, I love that song, I like a lot of your work,” I said, “considering the situation you find yourself in, and considering the juxtaposition of the song [“Dear Mama’] that reaches people like that, maybe there’s another way. I understand that the business you’re in is not—you can’t be a goody-two shoes in this business, but maybe there’s a way to inspire youth instead of—you know. Maybe there’s a way that you can use this talent of yours to inspire our youth, because they need somebody.”