When it comes to the fact that Tupac and Madonna once dated, most are shocked that their relationship even happened.
But in a letter penned from within his prison cell in 1995, Tupac revealed to his former flame of 18 months, that their pairing ran the risk of ruining his gangster image.
Apparently – as revealed in the late rapper's handwritten message - because she is white.
While serving out his sentence for sexual assault at the Clinton Correctional Facility, Tupac began the note, written on January 15, 1995 at 4:30 a.m., by referring to Madonna endearingly as ‘M’.
The three-page letter, which was published in portions by TMZ, revealed the rapper had "Waited a long time to finally write this mainly because I was struggling to find all the answers that I wouldn't leave any unanswered questions.”
The 'Material Girl' singer and 'Thug Life' rapper had first met in March 1993 after being introduced by actress Rosie Perez at the Soul Train Music Awards in LA.
Tupac’s brother Mopreme Shakur, even says that he played a part in the two being “a thing for minute.”
As told to Vlad TV, Mopreme reveals that Madonna gave him a message for Tupac, recalling, “I was just happy she was giving him a note. Everybody was there. I went over and gave it to him. He was about the business and then they linked up. I would take him to her house and s--t when we got back to LA."
But despite the pair having a seemingly strong relationship throughout 1994, Tupac apologises to Madonna within his letter, writing, “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.”
“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. I never meant to hurt you.”
Later in the script, Tupac references an interview Madonna had given wherein she allegedly said she was “’off to rehabilitate all the rappers and basketball players’, or something to that effect.”
"Those words cut me deep seeing how I had never known you to be with any rappers besides myself,” Tupac reveals. “It was at this moment out of hurt & a natural instinct to strike back and defend my heart & ego that I said a lot of things."
Expressing a sense of regret, Tupac continued, "Can you feel me? In the time since, as u can see, I have grown both spiritually and mentally. It no longer matters how I'm perceived," he said. "Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol."
The letter sums up with an extension of friendship from the rapper to the Queen of Pop, which also contains a word of warning.
“I offer my friendship once again this time my stronger & focused. If you are still interested I would like to further discuss this with you but some of it couldn't wait. I felt compelled to tell you...just in case anything happened 2 me. Please be careful Madonna. 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 5 bullets be proof of that!”
Ending with a P.S. Tupac finishes, “I don't know how you feel about visiting me but if you could find it in your heart I would love to speak face to face with you. It's funny but this experience has taught me to not take time 4 granted."
The iconic rapper, who is remembered for his social rights activism as well as his musical success, was fatally shot in a drive-by shooting in 1996.
His handwritten prison letter will be auctioned at Gotta Have Rock and Roll from July 19 to the 28, and although the starting bid is set at $US 100, 0000 ($131, 000 AUD), it's estimated the final price will settle at a much larger sum.