Giancarlo Esposito Recalls The Time Madonna Tried to Shoot Her Shot

Madonna is known as much for her love life – particularly her affinity for Black men – as her music and movies. Her relationships stay in the press. And now one Black actor is recalling a time the “Like a Prayer” singer tried to shoot her shot.

During a recent appearance on the Sirius XM podcast The Clay Cane Show, actor Giancarlo Esposito shared stories from some of the most memorable moments of his career so far, including meeting legendary author James Baldwin while working on the film adaptation of his book, “Go Tell It on the Mountain” and working with Whitney Houston on “Waiting to Exhale.” But one of his most interesting anecdotes was about his time working with Madonna on the 1985 film “Desperately Seeking Susan.”

Esposito, who had a small role in the film, said he shared a trailer with the Material Girl while filming the low-budget indie flick. The “Parish” star says he was in awe of her beauty and energy and was surprised when she made her move with a late-night phone call.

“Oh, man. Yeah, she hollered. She hollered. I mean, yeah,” he said. “I had given her my number, and I remember I got a phone call really late at night. And I was like, ‘Uh, who is this?’ And she’s like, ‘It’s me. It’s Madonna.’

As flattered as he was to hear from her, Esposito said he was in a relationship with the woman who would eventually become his wife at the time – and she had questions.

“[She] was like, ‘Who is that?’ And I was like, ‘Louise.’ ‘Louise who?’ I was like, ‘Madonna.’ She was like, ‘What? You know what time it is?’” he laughed.

Esposito is just one on a list of Black men Madonna set her sights on back in the day. In 1994, she had a brief relationship with former NBA bad boy Dennis Rodman. In a 1996 interview, Rodman said he ended things with Madge because he didn’t want to be known as “Madonna’s Playboy, her boy toy.”

And then, of course, there’s the time she spent with rapper Tupac. The unlikely pair also spent time together in the mid-nineties until the “All Eyez on Me” rapper ended things because she was white.

Pac broke it off with the singer in a 1995 letter, writing from prison, “For you to be seen with a Black man wouldn’t in any way jeopardize your career, if anything it would make you seem that much more open and exciting.” He continues, “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.”