Madonna Dated Tupac Shakur & 5 Other Surprises From The Singer

Madonna's list of ex-boyfriends just grew by one – one icon of rap!

During her an interview with Howard Stern on his SiriusXM radio show on Wednesday, the Queen of Pop revealed that she briefly dated the late rapper.

While talking about her infamous "Late Night With David Letterman" appearance from 1994, where she dropped numerous F bombs, Madonna mentioned the relationship.

"I was mad at [David Letterman] when I said the F-word a lot," she told Howard about the 1994 talk show appearance. "I was in a weird mood that day. I was dating Tupac Shakur at the time and the thing is [Tupac] got me all riled up on life in general. So when I went on the show, I was feeling very gangsta."


Tupac Shakur in 1994 (Getty) Here are five more gems from Madonna's 90-minute chat with Howard Stern:

Was Told Her Career Was Over In 1984

"I just dove for [my shoe] on the ground, my dress went up and my butt was showing… and I didn't know my skirt was up. So, I proceeded to sing the song laying down on the ground. I was just making the best of a situation, which is what I do," Madonna said of her iconic performance of "Like A Virgin" at the 1984 MTV VMAs. "After I got off stage, my manager was white as a ghost. He looked at me and he said, 'Do you know what you just did?' I looked at him and I said, 'Yeah, I lost my shoe onstage.' And he was like, 'No, your butt was showing for the entire song.' And he looked at me and he said, 'Your career is over.'"

Considered Michael Jackson A Kindred Spirit

"I could certainly relate to him on many levels, but he was also a very shy person," she said. "He was famous since he was a child and didn't really have a childhood. He was painfully shy… We didn't really have a relationship about me revealing myself to him, but making fun of the crazy world we were living and working in. We didn't talk about our childhoods... I think he felt eternally tortured. It was hard for him to look into people's eyes."

Not A Jealous Girlfriend

"[Warren Beatty] was [an incredible lover]. I'm not going to lie," Madonna said of her ex, who dated Brigitte Bardot, Julie Christie and Elle Macpherson, adding, "I have confidence in my skills."

She Left Artist Jean-Michel Basquiat Due To His Drug Use

"We always think we can fix people and we can't...just change yourself," she said of dating the late artist in the '80s. "I loved him… When I broke up with him he made me give [his paintings he painted for me] all back to him, and then he painted over all of them black."

Why She Quit Doing Ecstasy

"I tried some ecstasy in the '80s, but I felt so ill for so many days after taking it. It wasn't worth it," she told Howard, adding, "I'm pretty fun when I'm drunk."

2015 Grammy Awards: Madonna's Bizarre, Satanic Performance 'Living For Love' Sparks Outrage, Offends Christians

Madonna performs at the 57th annual Grammy Awards. Photo: AP Images

While world-famous pop singer Madonna is known for her shocking, often promiscuous music, her performance at the 2015 Grammy Awards reached disturbing new heights due to its overtly Satanic themes.

After being introduced by Miley Cyrus and Nicki Minaj as a "bada**, trouble-making international star," Madonna gave the first live performance of her new single, Living For Love, off her new album, "Rebel Heart" at the 57th Annual Awards on Sunday. Wearing a risque matador outfit, complete with red devil's horns, the 56-year-old mother-of-four danced across the stage with men dressed as demons.

The demons, who also wore revealing outfits, leaped around the "Crazy For You" singer and even simulated sexual acts with her while she sang the Gospel-influenced dance track.

Madonna then demanded the audience stand up and join in as she belted out lyrics, 'Love, love lift me,' before being pulled up into the air as the demons bowed down underneath her.

While the elaborate performance was praised by many critics, the satanic imagery and sexual overtones disturbed Christians, who took to social media to voice their opinions.

"It looks like Hollywood's fascination with demons and darkness is not going to end anytime soon...'And this is the condemnation, that light is come into the world, and men loved darkness rather than light, because their deeds were evil.' John 3:19" wrote radio host and pastor Geoffrey Grider.

"I'm disappointed by Madonna. It seems to me, that these global stars think they are just having a bit of fun...when what they are doing is literally playing with the devil... in their heart of hearts, do they really want to participate in the corruption of the masses? Is there anyone left I can admire?" wrote a YouTube user under a video of the performance.

This is not the first time performances at the Grammy Awards have offended those in the Christian community. Last year, Maddona, along with other artists, participated in a mass wedding involving 33 homosexual and heterosexual couples following a demonic perfromance by pop singer Katy Perry, prompting Christian singer Natalie Grant to leave the show.

At the time, Grant wrote on her Facebook page, "We left the Grammy's early. I've many thoughts about the show tonight, most of which are probably better left inside my head. But I'll say this: I've never been more honored to sing about Jesus and for Jesus. And I've never been more sure of the path I've chosen."

She later added, "I've judged no one. I hate no one. And I believe that every person has been created in the image of God. I will never stand on a street corner and wave a sign, I won't use my platform to engage in political arguments that will only divide and not unite. I will continue to pray that my life will be my message. I do have my own personal convictions that I live by, and I will continue to work out my own salvation with fear and trembling before the Lord. (Philippians 2:12)