Tupac‘s relationship with Madonna ran deeper than anyone knew.
In 2015, the Material Girl made headlines after revealing she had dated the rapper three years before his death in 1995. “One time I was mad at [David Letterman] when I said the f-word a lot, but the rest of the time was good,” Madonna told Howard Stern. “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 gangsta.” Later that year, the rapper’s brother, Mopreme Shakur, told Vlad TV he helped facilitate the romance. “She gave me a note to give to him; 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 L.A. Yeah…” he recalled.
On Wednesday, TMZ published portions of a letter—written Jan. 15, 1995 at 4:30 a.m.—that Tupac wrote to Madonna while serving time for sexual assault at Clinton Correctional Facility. Gotta Have Rock and Roll will auction off the letter between July 19-28 with a starting bid of $100,000; according to TMZ, the last letter written by the rapper fetched more than $170,000.