Legendary late rapper Tupac Amaru Shakur shot and killed over 2 decades ago up till today much is still being talk about him.
Not too much is known about the odd pairing, with the Vogue singer keeping the romance a secret up until 2015.
Now handwritten letters from when the California Love lyricist Late Tupac was in prison have been made public, lifting the lid on their unlikely relationship.
Madonna dated the legendary rapper before his murder in 1996.
The pair met each other for the first time in March 1993 at the Soul Train Music Awards in Los Angeles when Tupac was 24 and Madonna was 37.
The relationship is thought to have ended in February 1995 when he began serving a prison sentence for first-degree sexual abuse which stemmed from an incident in November 1993.
“I felt due to my 'image' I would be letting down half of the people who made me what I thought I was”Tupac Shakur
In the note which has been obtained by TMZ and is dated January 15 1995, Tupac noted that he dumped Madonna because of her race.
"I've waited a long time 2 finally write this," he began.
"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."
Tupac then goes on to address the reason behind their split, adding: "For you to be seen with a black man wouldn't in any way jeopardise your career, if anything it would make you seem 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."
Madonna kept quiet about their fling until a few years ago when she let it slip during an interview with Howard Stern.
The pop icon addressed an expletive-laden interview she gave on the Late Show With David Letterman on in 1994.
She said: "I was in a weird mood that day.
"I was dating Tupac Shakur at the time, and he had got me all riled up about life in general. So when I went on the show I was feeling very gangster."