At the ripe, young age of 56, Madonna can still break the Internet. She confirmed dating Tupac Shakur in the early-to-mid ‘90s, but don’t hold your breath for any details.
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Do the dates and details match up? Well, Howard Stern kicked things off by asking her about an interview with David Letterman. In theory, you find the date of the interview and go from there. That’s what we did. With the help of some old press clips and research, here’s a possible timeline of 2Pac and Madonna’s romance.
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November – December 1992 MTV Interview
The infamous 1992 MTV Very Merry Christmas interview where ‘Pac allegedly met “The Material Girl” for the first time. The dates match up, since this was an interview to promote a charity album featuring various artists, it was an occasion where the pre-Me Against The World 2Pac and the already famous Madonna would’ve have theoretically been in the same room.
Various Parts Of 1993 – 94
Convicted record executive Jimmy Henchmen told Vibe he connected with ‘Pac on the set of Above The Rim in New York. Henchmen says ‘Pac introduced him to Madonna, and in exchanged, he introduced Tupac to the man who would become known as “Hatian Jack.”
March 15, 1994 – Eighth Annual Soul Train Music Awards
According to Rosie Perez, she was stood up on a date for the 1994 Soul Train Music Awards, but Tupac offered to go with her in place of her unnamed companion. Perez says ‘Pac made mention of meeting up with Madonna.
March 19, 1994 – Snoop Dogg Appears On Saturday Night Live
This was Snoop Doggy Dogg’s first appearance on SNL, and he says Tupac came to smoke him out before the show. ‘Pac brought Madonna as a surprise guest, and the three of them blazed up the stickiest of the icky.
March 31, 1994 – Madonna’s Letterman interview
Based on Madonna’s interview with Howard Stern, she was dating 2Pac during her well-documented, profanity-laden interview with David Letterman. The Letterman interview aired March 31, 1994, so it was probably taped a day or two earlier.
Various Parts Of 1994 – Bedtime Stories
Promotional materials from the time suggest Madonna was working on her Bedtime Stories album from the beginning of 1993 through 1994. The album featured a duet with 2Pac entitled “I’d Rather Be Your Lover,” but it had to be scrapped to avoid additional controversy by the time the album dropped in 1994.
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August 16, 1994 – Madonna’s 36 Birthday
If Madonna indeed wanted to have 2Pac’s baby before her biological clock ran out of time, the dates kind of match up. From their reported dating period of 1993 through 1994, she would’ve been about 36. And this was back when in vitro fertilization was not as popular as it is today.
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November 30, 1994 – 2Pac Gets Shot
Just for context, the attempt on 2Pac’s life at Quad studios happened in November of 1994. If he and Madonna were dating, taking five shots at point blank range most likely would’ve put a damper in the relationship if they still were an item at the time.
Unknown Date 1994 – 1995
The well-known picture of Madonna, 2Pac, Sting, and Ingrid Casares was allegedly taken at a 1994 party in Tribeca, New York. Rumors have circulated about it being a pre-Golden Globes party. The 1994 Golden Globes took place in January, so it’s hard to imagine a possibly still-injured ‘Pac getting it in one month before his prison sentence started.
February 14 – October 19 – 2Pac In Prison
During his nine-months sentence at Clinton Correctional Facility 2Pac married Keisha Morris. It’s safe to assume the relationship with Madonna was over. However, ‘Pac says Madonna wrote him while in prison, and she also planned to visit before canceling the trip once it leaked to the press.
