Did Tupac Shakur have a secret fling with Whitney Houston?
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Did Tupac Shakur have a secret fling with Whitney Houston?

Death Row rapper Tupac Shakur is still considered one of the greatest rappers of all time. Full of passion and an advocate for social change during turbulent times, the rapper was one of the world’s most famous artists in the 1990s. However, despite his loud and aggressive side, the rapper could also be loving. Fans were always obsessed with Shakur’s love life, and, at one point, Whitney Houston strangely entered that realm.

Houston was one of the greatest vocalists of her generation and, akin to Shakur, was loved by the world for her unparalleled contributions to music. However, the chitchat of the two being romantically involved raised eyebrows in the ’90s and even now, fans have questions about where the rumour came from in the first place.

Usually, such a preposterous claim would be dismissed by fans quickly, but the rapper’s past actions made it a little harder for the public to deny the rumour so easily. From 1993 to 1995, the rapper openly dated the ‘Queen of Pop,’ Madonna. The two had met at the Soul Train Awards and continued to see each other romantically. However, upon his imprisonment, the ‘Hit Em Up’ rapper dumped Madge via a letter.

The passage, which TMZ has since published, reads, “For you to be seen with a black man wouldn’t in any way jeopardise your career if anything, it would make you seem that much more open and exciting. 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… It no longer matters how I’m perceived. Please understand my previous position as that of a young man with limited experience with an extremely famous sex symbol.”

Shakur did extend an olive branch and apologised for any hurt he may have caused, writing, “I would like to further discuss this with you, but some of it couldn’t wait. I felt compelled to tell you… just in case anything happened to me.”

People commonly use the colloquialism “there is no smoke without fire”. However, in 2016, Houston’s ex-husband, singer and songwriter Bobby Brown unleashed an inferno upon questioning fans. According to the ‘My Prerogative’ singer, the answer to the query fans had been making for years was a blunt and straightforward “yes”. In his 2016 memoir, Every Little Step, Brown wrote, “[Houston] did her share of cheating with quite a few of the producers and artists she worked with, including the late Tupac Shakur.”

The former New Edition member even claimed that he had slept with Madonna when she was with 2pac. All rather messy. Fans didn’t know whether or not this was factual or Brown making up salacious stories to get headlines. For many, it is still unknown. However, for those who take Brown’s word as gospel, the answer is a firm “yes”.

In the video below, you can hear Bobby Brown talking about the affair on the Art Of Dialogue podcast.