Tupac Shakur and Madonna shared a lot in common on both a professional and personal level (see: “Madonna MC: 10 Times Madame X Flexed Her Hip-Hop Cred“), so much so that Pac was driven to write a letter to Madonna during his highly-publicized stint in prison back in 1995. Now, following the pop queen’s failed attempt to appeal the sale of it last month, that letter will now go to auction for a starting price set in the six figures.

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One of the most significant music artifacts to ever come to auction. This handwritten love letter from Tupac Shakur to Madonna is being offered at auction for the first time ever. This now famous, extremely personal, three-page handwritten and signed letter was written by Tupac Shakur to Madonna from prison. Tupac addressed the letter to “M”, dated it, “Jan 15 1995, 9:30 A.M.” and signed it “Always, 2PAC, Tupac Shakur” in black ink on lined paper. The deep connection between Tupac and Madonna is seen throughout the letter. He writes about their relationship in terms of race and celebrity status, and how societal norms affect their relationship, writing “I must apologize to you. Because like you said I haven’t been the kind of friend I know I am capable of being. Not because I am evil or because you weren’t worthy but at the risk of sounding over dramatic, the effects of racism make it difficult for a young black man to properly show affection for an older white woman.” He further writes about his fears about his own death, which he feared would come soon, writing, “If there is any information you can share with me regarding Jack & crew please do it could very well be a matter of live & death”. The letter is going up for sale in less than a week on July 17th! Register now, link in bio! #gottahaverockandroll #tupacfan #tupacfans #tupac #tupacnews #2pacnews #madonna #madonnanews #madonnamemorabilia #madonnacollection #madonnacollector #madonnacollectors #tupacmemorabilia #tupacshakur #2pac #2pacvideos #news #rapnews #auctionnews #entertainmentnews #memorabilia #rapmemorabilia #musicmemorabilia #rockmemorabilia #auction #onlineauction #onlineauctions #rockauction #rapauction

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Tupac wrote this “love letter” during January 1995, a month after he and Charles Fuller had been convicted on rape charges and incarcerated with a multimillion-dollar bail. The three-page note reads very apologetic, mainly because it’s pretty much a “can-we-just-be-friends”-style break-up letter. One of the most prominent points he makes about needing the break came down to race unsurprisingly enough. He writes, “…at the risk of sounding over dramatic, the effects of racism make it difficult for a young black man to properly show affection for an older white woman. Can U understand that? [sic]” He goes on to state that the idea of them basically being a ’90s power couple, him being a West Coast Rap King and her being the Queen of Pop, would’ve made her seem “open & exciting” while making him look as if he’s “letting down” the rap community that uplifted him to that status in the first place. The emotional note is clearly a stamp of decades-old music history, but whether or not it evades the privacy of two pop icons, or if its even worth the minimum of $100,000 USD overall, is still up for debate.

The auction for Tupac’s love note (i.e. “friendzone letter”) to Madonna will go live starting next Wednesday (July 17) over on GottaHaveRockAndRoll.com. Hear the duo’s unreleased remix of her ‘Bedtime Stories‘ album cut “I’d Rather Be Your Lover” below: