Tupac’s sudden death in 1996 left behind a trail of questions about the late rapper’s life. But thanks to a letter obtained by TMZ, we get a rare glimpse at the man behind the larger than life persona.

The letter was written to Madonna by Tupac, and explains the reasons he decided to end their oft-rumored relationship. Chief among them was race, specifically the way people would perceive him if he dated a white woman and the pointed double standard involved.

“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 and exciting,” he wrote. “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. I never meant to hurt you.”

The letter was dated January 15, 1995, which the Washington Post points out places it around the time Tupac was incarcerated at New York’s Clinton Correctional Facility for sexual assault charges. At one point, he even asks Madonna to visit him in person.

It’s a stunning look inside the enigmatic relationship between two superstars at the height of their fame. The letter instantly becomes one of the more essential documents of Tupac’s life, as he explains to Madonna that he had recently undergone a kind of awakening. After telling her that her comments about dating other rappers and basketball players hurt him and that he felt overwhelmed dating “an extremely famous sex symbol” he says that he had “grown both spiritually and mentally.”

Tupac’s life has been the subject of much debate recently, after the release of the widely panned biopic All Eyez on Me. The film was heavily criticized for oversimplifying what was a complex and conflicted existence. New York magazine’s Emily Yoshida called it a “more than a faithful adaptation of the rapper’s Wikipedia entry,” that failed to “explore the experience of the man himself.” In other words, for a penetrating look at the life of one of our most indelible cultural icons, skip the movie, and read the letter here.