Madonna and Tupac briefly dated back in 1993, three years before the rapper was shot. Worried by the perception Tupac might receive by dating an 'older white woman' he wrote to her from his prison cell calling the whole thing off. Now, after years of legal battles, the letter is set to be auctioned off for a huge price tag.
The emotionally charged letter asks Madonna for her friendship and asks if she'd visit him in prison so they could talk about it face to face.
The letter reads: "For you to be seen with a black man wouldn't in any way jeopardise your career, if anything it would make you seem that much more open and 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."
Madonna. Credit: PA
It looks like the letter was a form of closure for both stars as he wrote: "I've waited a long time to finally write this.
"Mainly because I was struggling to find all the answers so that I wouldn't leave any unanswered questions.
"First and foremost I must apologise to you because, like you said, I haven't been the kind of friend I know I am capable of being."
He then goes on: "In the time since, as you can see, I have grown both spiritually and mentally.
"It no longer matters how I'm perceived. Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol."
Tupac ends the letter by pleading with the singer to 'be careful', writing: "Everyone is not as honourable as they seem. There are those whose hearts bleed with envy and evil. They would not hesitate to do you harm! Let my five bullets be proof of that."
The first part of the letter from Tupac to Madonna Credit: Press Association Images / GottaHaveRockandRoll.com
The second part of the letter from Tupac to Madonna Credit: Press Association Images / GottaHaveRockandRoll.com
Tupac asks Madonna to visit him in prison Press Association Images / GottaHaveRockandRoll.com
In 2017, Madonna tried to halt an auction of the letter and other personal belongings owned by Tupac.
Madonna said: "The fact that I have attained celebrity status as a result of success in my career does not obviate my right to maintain my privacy, including with regard to highly personal items".
The Material Girl alleged that those possessions had been stolen and had no idea that they were no longer in her possession.
Despite her plea, TMZ has obtained court documents claiming that the case had been thrown out and Tupac's letter was free to be sold.
It's due to go under the hammer on 17 July and is expected to reach an eye watering $300,000 (£239,000).
Featured Image Credit: Credit: Paramount