Tupac Shakur has been dead for nearly 30 years – but he’s still making tongues wag in death as fans muse over his brief relationship with Queen of Pop Madonna.
The California Love rapper met his tragic end after a drive by shooting in Las Vegas in 1996, but just two years before that he enjoyed a steamy romance with the world’s biggest popstar.
Though the Vogue songstress posthumously outed their relationship during an interview with Howard Stern 20 years later, it was Tupac’s ink to paper about the ‘magic’ they shared that has captivated fans’ attention.
Close friends and family have long labelled the star a ladies man who dated several famous women before his untimely death, including Jada Pinkett Smith and Jasmine Guy.
Though at the time Tupac was a bonafide rapstar, he was serving a stint at New York‘s largest prison, Rikers Island, following a conviction for first-degree 𝑠e𝑥ual abuse.
This along with a string of other controversies – including a public spat with Janet Jackson over her alleged request for Tupac to take a HIV test before kissing her in 1993 film Poetic Justice – had left his promising career on the rocks.
Throughout the 80s and 90s, the Like A Virgin hitmaker was linked to a string of male celebs such as Sean Penn, Vanilla Ice, Dennis Rodman and even Michael Jackson.
He was later convicted of the first-degree 𝑠e𝑥ual abuse of a woman named Ayanna Jackson in December 1994, and was sentenced to up to four-and-half years in prison – although he only spent nine months behind bars.
Actress Rosie Perez introduced the star-crossed lovers, and later boasted that she played matchmaker to her ‘good friend’ Tupac and Madonna.
Similarly, fellow ex Deathrow records collaborator, Snoop Dogg, recounted the moment he spotted the ex-lovers together just before a music performance.
Though neither star has ever admitted to a secret rendezvous at Rikers Island, court documents obtained by DailyMailTV in 2017 suggest the singer may have paid her former flame a visit.
The same year the singer filed an emergency court order to stop the auction of Tupac’s letter, which court papers revealed was expected to fetch up up to a whopping $400,000.
However in 2019 Madonna lost the appeal to halt the auction, with the New York State Appeals Court ruling the star can’t sue her former friend Darlene Lutz for selling the letter to an online auction house.