The late rapper - who died 21 years ago when he was shot six times in a drive-by shooting - dated the 'Like a Virgin' hitmaker for three years before his death and has admitted in a gripping letter he penned when he was in prison that he ended their secret relationship because of their different cultures and how his ''people'' would react.
He wrote at the time: ''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. 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.(sic)''
Although he called it quits with the 58-year-old singer, he claimed in his letter that he never meant to ''hurt'' her and offered out his hand for a possible friendship.
He explained: ''I never meant to hurt you. 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 a extremely famous sex symbol.
''I offer my friendship once again time this time much stronger and focused. If you are still interested I would like to further discuss this with you but some it couldn't wait. I felt compelled to tell you... just in case anything happened to 2 me.''
The letter is set to go up for auction between July 19 and July 29 at Gotta Roll, according to TMZ, and the bids will start at $100,000.
Following her relationship with Tupac, Madonna went on to have daughter Lourdes, 20, with ex-partner Carlos Leon, son Rocco, 16, with her ex-husband Guy Ritchie, and adopted four children; David, 11, Mercy, 11, Stelle and Estere, four.
From their newest EP 'What Did You Think When You Made Me This Way', Nothing But Thieves drop the lyric video for their single 'Take This Lonely...
The Lumineers honour their friend and hero Tom Petty with a sensational cover of his 1996 song 'Walls' from the 'She's the One' soundtrack.
Watch Olly Murs get his nerd on as he blags his way into an exclusive Snoop Dogg party (where Rowan Atkinson is the bartender) in the video for their...
From 'Happy' to 'Banana Pancakes', these are soaked in positivity.
Mariah Carey is the picture of glamour in the black and white video for her brand new single 'With You'. It's the lead single from her forthcoming...
Eminem draws attention to the negative response his 2017 album 'Revival' received in the video for his latest song 'Venom'; a song recorded for the...
With the recent release of her third, very well received album 'Hunter' just behind her, Anna had plenty of relatively new songs to showcase.