The Material Girl made the confession during an interview with U.S. shock jock Howard Stern on Wednesday (11Mar15), mentioning the romance while discussing an old interview with TV host David Letterman in which she said the word 'f**k' 14 times.
Madonna told Stern ,"That's how I flirt with people... One time I was mad at him when I said the F-word a lot. I was in a weird mood that day. I was dating Tupac Shakur at the time and the thing is he got me all riled up on life in general. So when I went on the show I was feeling very gangster."
When Stern pressed the singer for more information about her relationship with Shakur, she insisted the gossip had already been made public.
In 2007, an unauthorised biography titled Madonna: Like an Icon detailed a rumoured romance between the two music superstars, shortly before the rapper's death in 1996, while last year (14), Rosie Perez revealed she first introduced the pair during the 1993 Soul Train Music Awards.
Perez recruited her good friend Shakur to be her date, and he only agreed on the condition that the actress would set him up with Madonna.