Inside Madonna’s strained relationship with brother Christopher Ciccone following news of his death

Madonna suffered the loss of her baby brother Christopher Ciccone – whom she affectionately called ‘Chrissy’ – last Friday, at age 63, following a two-year battle with prostate cancer.

‘Christopher’s loving spouse [of eight years, Ray Thacker] was faithfully by his side during the final stages of the cancer that would ultimately end his life,’ his representative confirmed to DailyMail.com.

The 66-year-old Queen of Pop was closer to Christopher than any of her seven siblings, first hiring him as an uncredited back-up dancer in her music videos for Holiday (1983) and Lucky Star (1984).

‘My brother Christopher’s gay,’ Madonna publicly outed Ciccone in her 1991 interview with The Advocate.

‘And he and I have always been the closest members of my family.’

Madonna suffered the loss of her baby brother Christopher Ciccone – whom she affectionately called ‘Chrissy’ – last Friday, at age 63, following a two-year battle with prostate cancer (pictured in 1995)

His representative confirmed to DailyMail.com: ‘Christopher’s loving spouse [of eight years, Ray Thacker] was faithfully by his side during the final stages of the cancer that would ultimately end his life’ (pictured in 2016)

The self-made superstar eventually promoted the avid painter to the positions of personal assistant, backstage dresser, interior designer, art director for her 57-date Blond Ambition World Tour in 1990, and director for her 39-date The Girlie Show in 1993.

Christopher was secretly horrified when Madonna decided to film a scene of Alek Keshishian’s 1991 documentary Truth or Dare at the grave of their late mother Madonna Fortin-Ciccone – calling it a ‘turning point’ in their relationship.

‘I kept it inside but I thought to myself, “Okay, there are no boundaries now.” You know, my mother’s now become a side — a bit player in her life, life story, and it hurt me. And I — my, my opinion of her altered at that moment. I never said anything about it,’ Ciccone told GMA back in 2008.

‘I think, ultimately, she’s a lonely person and, unfortunately, it, it truly is lonely at the top.’

In 1994, the Bernhardt Furniture designer became addicted to cocaine and the seven-time Grammy winner warned him she would not work with him again unless he entered the rehab she paid for him to attend.

Christopher claimed Madonna’s 2000 nuptials to second husband Guy Ritchie was the ‘death knell for my relationship with her’ and described him as ‘a man who seems so insecure in his masculinity that he thrives on homophobia.’

Ciccone ‘never got along’ with the 56-year-old British filmmaker, whose friends allegedly made jokes about ‘poofters’ during their wedding toasts.

‘[Y]ou have never in the entire time I have worked for you since 1985 paid me even close to what I was worth,’ Christopher wrote in a scathing email to the twice-divorced mother-of-six in 2000.

The 66-year-old Queen of Pop was closer to Christopher than any of her seven siblings, first hiring him as an uncredited back-up dancer in her music videos for Holiday (1983) and Lucky Star (1984, pictured)

Madonna publicly outed Ciccone in her 1991 interview with The Advocate: ‘My brother Christopher’s gay, and he and I have always been the closest members of my family’ (pictured in 1991)

Ciccone told GMA back in 2008: ‘I kept it inside but I thought to myself, “Okay, there are no boundaries now.” You know, my mother’s now become a side — a bit player in her life, life story, and it hurt me. And I — my, my opinion of her altered at that moment. I never said anything about it’

Christopher claimed Madonna’s 2000 nuptials to second husband Guy Ritchie (L, pictured in 2000) was the ‘death knell for my relationship with her’ and described him as ‘a man who seems so insecure in his masculinity that he thrives on homophobia’

Ciccone ‘never got along’ with the 56-year-old British filmmaker (R, pictured in 2001), whose friends allegedly made jokes about ‘poofters’ during their wedding toasts

‘I gave up my f***ing life to help make you the evil queen you are today… 15 years listening to your b****ing, egotistical rantings, mediocre talent, and a lack of taste that would stun the ages… Every ounce of talent you have, you have sucked dry from me and the people around you… I certainly have never worked for you for the money…

‘Now you accuse me of lying and cheating you… you’ve got some f***ing nerve… as usual… you have lost all sense of reality… I guess I always thought that one day you’d see my worth and behave accordingly… but you never did… a little f***ing respect was all I ever wanted from you and you couldn’t even manage that.’

In 2008, Ciccone earned ‘seven figures’ to team up with author Wendy Leigh and co-write a bitter, 352-page tell-all titled Life with My Sister Madonna.

But by 2012, the High Art Productions director told The Evening Standard that he and Madonna had made peace and were ‘back in contact with each other.’

‘As far as I’m concerned, we’re good,’ Christopher revealed.

‘Although I haven’t seen her for a long time. We’re back to being a brother and sister. I don’t work for her, and it’s better this way…I couldn’t be more proud of her. She is a force to be reckoned with. Does she have Barbra Streisand’s voice? No. Can she dance like Martha Graham? Probably not. But the combination of her abilities has made her great, and left a huge legacy for her, and through her, for me. So yeah, God bless her.’

Ciccone lived in Suttons Bay, MI where their 93-year-old father Silvio Ciccone continues to run the Ciccone Vineyard & Winery – which closed last Friday in his remembrance.

On September 24, the Italian-American family also suffered the loss of Silvio’s second wife Joan Clare Ciccone, at age 81, ‘after a brief encounter with a very aggressive cancer.’

Christopher wrote in a scathing email to the twice-divorced mother-of-six in 2000: ‘[Y]ou have never in the entire time I have worked for you since 1985 paid me even close to what I was worth. I gave up my f***ing life to help make you the evil queen you are today… 15 years listening to your b****ing, egotistical rantings, mediocre talent, and a lack of taste that would stun the ages… Every ounce of talent you have, you have sucked dry from me and the people around you… I certainly have never worked for you for the money’

He continued: ‘Now you accuse me of lying and cheating you… you’ve got some f***ing nerve… as usual… you have lost all sense of reality… I guess I always thought that one day you’d see my worth and behave accordingly… but you never did… a little f***ing respect was all I ever wanted from you and you couldn’t even manage that’

In 2008, Ciccone earned ‘seven figures’ to team up with author Wendy Leigh and co-write a bitter, 352-page tell-all titled Life with My Sister Madonna

But by 2012 (pictured), the High Art Productions director told The Evening Standard that he and Madonna had made peace and were ‘back in contact with each other’

Christopher revealed: ‘As far as I’m concerned, we’re good. Although I haven’t seen her for a long time. We’re back to being a brother and sister. I don’t work for her, and it’s better this way…I couldn’t be more proud of her. She is a force to be reckoned with. Does she have Barbra Streisand’s voice? No. Can she dance like Martha Graham? Probably not. But the combination of her abilities has made her great, and left a huge legacy for her, and through her, for me. So yeah, God bless her’

Ciccone lived in Suttons Bay, MI where their 93-year-old father Silvio Ciccone continues to run the Ciccone Vineyard & Winery – which closed last Friday in his remembrance

On September 24, the Italian-American family also suffered the loss of Silvio’s (R, pictured in 2021) second wife Joan Clare Ciccone (L), at age 81, ‘after a brief encounter with a very aggressive cancer’

This, after Madonna and Christopher’s eldest brother Anthony Ciccone (pictured in 2023) passed away, at age 66, in February 2023 from respiratory failure and throat cancer after falling victim to years of alcoholism and homelessness

It’s worth noting that The Material Girl (pictured last Tuesday) is lucky to be alive following her June 24, 2023 hospitalization for ‘a serious bacterial infection’ during which she was in a 48-hour medically induced coma

Madge wrote on Instagram on Monday: ‘He was a painter a poet and a visionary. I admired him. He had impeccable taste. And a sharp tongue, Which he sometimes used against me but I always forgave him. We soared the highest heights together. And floundered in the lowest lows. Somehow, we always found each other again and We held hands and we kept dancing’ (pictured in 2008)

Madonna continued: ‘The last few years have not been easy. We did not speak for sometime but when my brother got sick, we found our way back to each other. I did my best to keep him alive as long as possible. He was in so much pain towards the end. Once again, we held hands. We closed our eyes and we danced together. I’m glad he’s not suffering anymore. There will never be anyone like him. I know he’s dancing somewhere’ (pictured in 2022)

This, after Madonna and Christopher’s eldest brother Anthony Ciccone passed away, at age 66, in February 2023 from respiratory failure and throat cancer after falling victim to years of alcoholism and homelessness.

It’s worth noting that The Material Girl is lucky to be alive following her June 24, 2023 hospitalization for ‘a serious bacterial infection’ during which she was in a 48-hour medically induced coma.

There were a total of eight Ciccone siblings including Madonna and Christopher’s sister Paula, sister Melanie, and brother Marty as well as their half-siblings Jennifer and Mario (through Silvio’s second marriage).

‘He was a painter a poet and a visionary. I admired him. He had impeccable taste. And a sharp tongue, Which he sometimes used against me but I always forgave him,’ Madge wrote on Instagram on Monday.

‘We soared the highest heights together. And floundered in the lowest lows. Somehow, we always found each other again and We held hands and we kept dancing. The last few years have not been easy. We did not speak for sometime.

‘But when my brother got sick, we found our way back to each other. I did my best to keep him alive as long as possible. He was in so much pain towards the end. Once again, we held hands. We closed our eyes and we danced together. I’m glad he’s not suffering anymore. There will never be anyone like him. I know he’s dancing somewhere.’

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