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. "They were a thing for a minute." (In 2014, Rosie Perez told Wendy Williams she played a role in introducing the former couple.)
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.