Cybill Shepherd’s bizarre fan moment with Madonna left the pop star visibly startled in resurfaced video

Madonna has survived too many fan encounters because of their blind devotion towards her.
PUBLISHED MAR 2, 2025
(L) Cybill Shepherd at People's Choice Awards in Universal City, CA March 11, 1990: (R) Madonna during Herb Ritts Birthday Party 1990 in LA, CA. (Cover Image Source: Getty Images| (L) Photo by Barry King; (R) Photo by Ralph Dominguez)
(L) Cybill Shepherd at People's Choice Awards in Universal City, CA March 11, 1990: (R) Madonna during Herb Ritts Birthday Party 1990 in LA, CA. (Cover Image Source: Getty Images| (L) Photo by Barry King; (R) Photo by Ralph Dominguez)

Cybill Shepherd had an overwhelming fan moment in 2007 when she spotted Madonna and couldn’t contain her excitement. Shepherd was nearby when the ‘Queen of Pop’ finished her interview with Today’s Meredith Vieira and walked out of the studio. As per TMZ, the 'Moonlighting' star ambushed the Grammy winner, screaming, 'It’s Cybill Shepherd! It’s Cybill Shepherd! It’s Cybill Shepherd!' before giving Madonna an impromptu hug. Madonna was visibly taken aback, likely not recognizing Shepherd, but she handled the situation gracefully.



 

The Things reported that the ‘Like a Prayer’ singer had just left the set of a heated interview with Vieira, where she defended her close friend Rosie O’Donnell in her feud with Donald Trump. Comedian O'Donnell had made some disparaging remarks about Trump's dating history and his dwindling financial status while the latter was involved in a scandal surrounding his Miss Universe organization. She said Trump 'inherited a lot of money' but had been 'bankrupt so many times.' This didn’t sit well with the real estate mogul, who fired back insults at O’Donnell.



 

When the journalist urged Madonna to pick a side, she was caught in the middle and disclosed that she had been communicating with O'Donnell via email regularly. "She's a stand-up comic. I think all stand-up comics talk about provocative things in their monologues before shows, and I think that's a commonplace thing," the 'Frozen' singer said. "I don't know exactly the content of what she said, but I have a feeling that if every stand-up comic was penalized for saying politically incorrect things or provocative things, I think they'd all be hung in the public square."

Rosie O'Donnell and Madonna at 'Taboo' premiere at The Plymouth Theater in New York, November 2003. (Image Source: Getty Images| Photo by Bruce Glikas)
Rosie O'Donnell and Madonna at 'Taboo' premiere at The Plymouth Theater in New York, November 2003. (Image Source: Getty Images| Photo by Bruce Glikas)

Meanwhile, Madonna has been known for her reckless behavior around fans, but they still adore her. In 2016, she almost got sued for yanking down 17-year-old Josephine Georgiou’s strapless top, causing a major wardrobe malfunction. The incident happened when the teen joined the 'Material Girl' on stage during the latter's packed concert in Brisbane, Australia. As per The Guardian, “She’s the kind of girl you just want to slap on the ass,” Madonna yelled adding, “And pull." To the audience's shocked applause, then in a bizarre move, she grabbed Georgiou's corset top and pulled it down, momentarily exposing one breast. 



 

“I’m sorry, sexual harassment,” she mocked. “You can do the same to me. Good luck,” she said while gesturing Georgiou to pull her costume as revenge. But the teen did not retaliate, however, she called it the "best moment of her life" and decided not to sue the pop icon for the misconduct and embarrassment. “She was calling me a Victoria’s Secret model the whole time I was on stage, which is so flattering,” the teen gushed with blind adoration. “Only I get to decide if I’m humiliated or not. Why would people assume I am humiliated by my own breast, nipple, or body?" she questioned. Fortunately, Madonna's supporters' raging devotion spared her from legal action

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