The late rapper wrote to the singer in a revealing letter he penned in jail obtained by TMZ. He wrote: “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.”
The letter is set to go up for auction from July 19-28 at Gotta Have Rock and Roll. The starting bid is $100,000.
Madonna previously revealed that she once dated the late rapper in 2015.
Speaking to SiriusXM radio host Howard Stern, Madonna spoke about a 1994 appearance on the Late Show With David Letterman, saying: “I was mad at [David Letterman] when I said the F-word a lot. I was in a weird mood that day. I was dating Tupac Shakur at the time and the thing is he got me all riled up on life in general. So when I went on the show I was feeling very gangsta.”
Madonna’s romantic involvement with Shakur had been the subject of rumours over the years, with an unauthorised 2007 biography called Madonna: Like An Icon previously claiming it to be true.
Meanwhile, it was recently revealed a new Tupac documentary is in development.
Officially authorised by the late rapper’s family, the new film will be directed by the acclaimed 12 Years A Slave filmmaker Steve McQueen and co-produced by Amarau Entertainment (the company founded by Tupac’s mother Afeni to manage her son’s posthumous releases) and Shakur estate representative Tom Whalley.
“I am extremely moved and excited to be exploring the life and times of this legendary artist,” McQueen said.
“I attended NYU film school in 1993 and can remember the unfolding hip-hop world and mine overlapping with Tupac’s through a mutual friend in a small way. Few, if any shined brighter than Tupac Shakur. I look forward to working closely with his family to tell the unvarnished story of this talented man.”
Tupac was recently the subject of a separate biopic, All Eyez On Me.