Tupac dated Madonna for a little over a year in 1993 after they were set up by pal Rosie Perez at the Soul Train Music Awards. Still, it wasn't until 2015 that Madonna confirmed their relationship in an interview with Howard Stern. "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 recalled. "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."
In 2017, TMZ published a letter that Tupac had written to Madonna while he was serving time at the Clinton Correctional Facility. In the heartbreaking note, which was dated Jan. 15, 1995, Tupac broke up with Madonna because of her race. "Can u understand that? For you to be seen with a black man wouldn't in any way jeopardize your career," the rapper wrote. "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. I never meant to hurt you."