Madonna has lost her ‘closest’ sibling following the death of her brother, Christopher Ciccone, who passed away aged 63 on October 4.
But despite their close bond, it wasn’t always happily families for the Michigan-born singer, 66, and the baby brother she affectionately called ‘Chrissy’.
He once worked as her backup dancer, personal dresser and art director, until their very public feud erupted in 2000 – before they finally made their peace in 2012.
Theirs isn’t the only rocky sibling relationship endured by Madonna, whose half-sister Jennifer wasn’t invited to her famous relative’s two weddings.
Her eldest brother Anthony, meanwhile, once suggested publicly that his family had turned their backs on him after he became homeless while suffering with alcoholism.
Once Madonna’s closest sibling, Christopher began his career as her assistant, dresser, stylist and artistic director (pictured in 1995)
But while the Ciccone siblings have been involved in many arguments over the years, they are said to have gathered around the sister after the megastar was hospitalised with a serious bacterial infection in 2023.
Sisters Paula, Melanie and Jennifer – and brothers: Martin, Christopher and Mario – are believed to have visited the superstar while she was at the ICU in New York.
Despite Madonna’s extreme fame and constant attention, her seven siblings, and their 93-year-old father Silvio, have largely stayed out of the spotlight.
The first five Ciccone siblings grew up in the suburbs of Detroit to Catholic parents, an Italian-American father and French-Canadian mother Madonna (the popstar was named after her).
Tragedy struck in 1963 when the children’s mother died at just 30 of breast cancer. Madonna, who was only five at the time, has said she would be a completely different person if her mother had not died so young.
In 1966, Madonna’s father married the family’s housekeeper Joan Gustafson and they had two children, Jennifer and Mario.
The children adjusted with difficulty. Madonna, particularly unhappy about her father’s remarriage, rebelled, straining their relationship for many years.
Here, FEMAIL delves into the lives of Madonna’s siblings – which have been blighted by homelessness, alcoholism and feuds…
Anthony Ciccone: Battled homelessness and alcoholism before he died aged 66, in February 2023
Madonna’s oldest brother, Anthony Ciccone (pictured), sadly passed away last year, after a troubled life including time living on the street and battling alcoholism
Madonna’s oldest brother, Anthony Ciccone, sadly passed away last year, after a troubled life including time living on the street and battling alcoholism.
Anthony mostly stayed in Michigan and worked for their father, before falling victim to alcoholism and homelessness. But like Madonna, he also spent time in New York in his 30s in the late 1980s.
Carolina Gengo, 59, who dated him at the time, described him in a positive light. ‘He was a lost soul trying to find his way but he was a good person,’ she told Dailymail.com.
‘He had books everywhere, that was all he really had. He was into reading about life and philosophy,’ said Gengo. ‘And he wanted to sit around and talk about it,’ she added.
‘He talked about what it was like being the brother of Madonna, he didn’t like being known as the brother of Madonna’, she said.
Gengo recounted one occasion when on his birthday his sister’s assistant called to ask how much money he wanted as a gift. That, she said, alienated him.
After some years of sleeping rough under a bridge in Michigan, Madonna’s family said they would reincorporate estranged Anthony in 2017.
It came after he suggested publicly that his family had turned their backs on him. ‘I’m a zero in their eyes; a non-person, an embarrassment,’ he told the Daily Mail in 2011. ‘If I froze to death, my family probably wouldn’t know or care about it for six months.’
Anthony said at the time that he had been living under a river bridge in Michigan with a sleeping bag and his sole companion, another street dweller named Michael.
He also claimed he once worked in Alaska’s fishing industry and as a photographer’s assistant in New York.
But tougher times saw him making a few dollars doing odd jobs and collecting bottles and cans from people’s dustbins.
Madonna had known about his plight, and repeatedly offered to help by paying for him to go into rehab. His father also offered to give him his job back if he got professional help.
He had not always been receptive though. ‘My family seem to think rehab is some kind of magic panacea for life’s ills,’ he once said.
Nonetheless things appeared to look up for Anthony after a stint in rehab in 2017 and his reintegration to family life.
Karen McCarthy, a founder of rehab clinic Dann’s House, confirmed his stay, telling the Sunday People: ‘Anthony loved it at Dann’s House for quite a while, and made significant improvements in his life while he was with us.
‘Dann’s House does good work with people who are vulnerable. We’ve seen tremendous, positive results.’
In a statement following his death, Joe Henry, who is the husband of Madonna’s sister Melanie Ciccone, wrote: ‘My brother-in-law, Anthony Gerard Ciccone, exited this earthly plane last evening. I’ve known him since I was 15, in the spring of our lives in Michigan so many years now gone.’
‘Anthony was a complex character; and god knows: we tangled in moments, as true brothers can. But I loved him, and understood him better than I was sometimes willing to let on,’ he added.
‘But trouble fades; and family remains – with hands reached across the table. Farewell, then, brother Anthony. I want to think the god your blessed mother (and mine) believed in has her there, waiting to receive you. At least for today, no one shall dissuade me from this vision,’ said Henry, ending his note.
Christopher Ciccone: Former personal dresser who wrote a tell-all book about sister before he died aged 63 in October 2024
They fell out in 2003 when she dropped him as her tour director, the tell-all memoir, Life With My Sister Madonna, was published in 2008. Pictured in the 1990s
Madonna suffered the loss of her baby brother Christopher Ciccone – whom she affectionately called ‘Chrissy’ – earlier this month, 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 backup dancer in her music videos for Holiday (1983) and Lucky Star (1984).
Christopher then worked as his sister’s personal dresser and art director until their very public feud erupted in 2000.
He described being the ‘one person’ who could take it when the singer screamed at him backstage and how he was the only one in her circle who knew the truth about her past, which she frequently ‘mythologised’.
However, the sibling’s relationship began to fracture in the late 1990s – as Christopher began to grow increasingly resentful over having given up his artistic dreams to support his sister’s career.
In 2000, Christopher famously labelled Madonna an ‘evil queen’ in a leaked email, where he lamented ‘giving up [his] f***ing life’ for his sister’s ‘mediocre talent’.
Eight years later, Madonna’s estranged brother reportedly earned ‘seven figures’ to team up with author Wendy Leigh to co-write the tell-all book Life with My Sister Madonna.
Madonna and Christopher grew up together in Michigan and learned to dance together. Then Christopher followed Madonna to New York, where she began her long journey to wealth and superstardom (Pictured at the Vanity Fair Oscar Party in 1998)
Madonna, centre, in 1970 with, from left, sister Paula, Uncle Chris, brothers Christopher and Marty, sister Melanie, stepmother Joan and father Silvio
In the 352-page book, Christopher made a cruel jibe about his sister’s ‘fat’ midriff during The Virgin Tour back in 1985 and said Madonna would become a ‘basket case’ when being interviewed on TV.
What’s more, he also described the vicious cycle where dancers would ‘fall under Madonna’s spell’ only to later be ‘hurtled out in the cold’ after getting ‘too close for comfort’.
In 1985, Christopher turned his back on his promising career as an artist in New York to become his younger sister’s backing dancer. He would later work as her dresser and then became the art director for her 1990 Blond Ambition tour.
However, he became resentful over turning his back on his own artistic career to support his sister.
Christopher wrote in a scathing email in 2000: ‘You 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…
‘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 his book, Christopher claims he only became a backing dancer in the first place because someone dropped out and Madonna desperately needed a replacement. He says he was only paid $200 for the Lucky Star video.
Pictured: Madonna going to her first communion in 1967 with her siblings – as Christopher sits in the front seat
Detailing some of his worst experiences working with his sister, Christopher said Madonna called him a ‘piece of s**t’ for not pushing out the little finger on her long black gloves.
On another occasion, he claims Madonna left him close to tears when she yelled: ‘Hurry the f*** up or I’ll f***ing fire you right now’.
Although he considered quitting the job, Christopher said he was the only person Madonna could really speak to – and therefore decided to ‘endure the abuse’.
During his time as Madonna’s dresser, her brother says that his peers would have struggled to cater for so many costume changes – but it was necessary for the amount the star sweated on stage.
As part of the job, Christopher would have to pick up his sister’s ‘sweaty underwear’ off of dressing room floors – and admitted he would be ‘humiliated if anyone in his life knew’ about it.
Everyone assumed he was by his sister’s side as a companion and assistant, rather than her dresser, and he did not set them straight.
In her 1991 interview with The Advocate, Madonna famously outed her brother – telling the reporter: ‘My brother Christopher’s gay and he and I have always been the closest members of my family.’
In his book, Christopher opened up about how he struggled to understand his sister’s decision to share such a personal detail of his life.
Rift: In 2008, the artist’s brother caused a stir with his explosive book Life With My Sister Madonna, in which he detailed their relationship from his perspective (pictured in 1999)
He wrote in his book: ‘Without asking me, without giving me a say in the decision, she has taken it upon herself to out me.
‘I know that she hasn’t for a moment considered whether my homosexuality is public knowledge, the reality that our grandmother doesn’t know about it, and neither does our extended family nor anyone outside our circle of friends.
‘Besides, it has always been my choice whether, when, or when to come out, not Madonna’s.’
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.’
Last Sunday, the singer posted a carousel of photos to her Instagram featuring her and Christopher, who died following a battle with cancer.
In a lengthy caption she honoured her sibling and noted the pair had been able to reconcile prior to his death.
Martin Ciccone: Recovering alcoholic and voice over artist
Like his late brother Anthony, Martin Ciccone, 65, has suffered a troubled past in which he’s battled alcohol abuse, DUI arrests, time in jail, and multiple stints in rehab
Like his late brother Anthony, Martin Ciccone, 65, has suffered a troubled past in which he’s battled alcohol abuse, DUI arrests, time in jail, and multiple stints in rehab.
In 2013, while working at a rehab centre in Hollywood for alcoholics and drug addicts, Martin told how his famous sister was helping him out financially by paying for a new set of false teeth for him.
He said: ‘We are on good terms and she’s helping me out. She’s getting me some new teeth. I’m hoping to start doing voiceover work again for cartoons and video games and get back on my feet.’
He’s also had a stint in the US army, and followed in his sister’s footsteps with a music career.
In 1994, he released a debut rap album under the name MC Ciccone, which included numerous bitter digs at his sister.
In 1999, after being without a record contact for several years, he was finally persuaded by Madonna to enter rehab to deal with his alcohol problem — which she paid for — causing him to miss her second wedding.
He started a restaurant in Los Angeles, and went back into rehab again in 2003.
Divorced with a daughter, he lives in Los Angeles and is trying to make it as a voice-over artist. He and Madonna are said to be in friendly contact.
Paula Ciccone: ‘Rock of siblings’ that runs family vineyard
A year younger than her famous sibling, if you saw Paula on the street it would be hard to conceive that this normal-looking 60-something is even vaguely connected to the global superstar, never mind one of her closest relatives
A year younger than her famous sibling, if you saw Paula on the street it would be hard to conceive that this normal-looking 60-something is even vaguely connected to the global superstar, never mind one of her closest relatives.
Head winemaker at the family’s vineyard in Michigan, she is more commonly to be found in fleeces and jeans than corsets or leather.
Intensely private — it’s unclear if she has a partner — Paula, who shared a childhood bedroom with Madonna, is at heart a bashful introvert.
Perched atop a hill on the picturesque Leelanau Peninsula, with panoramic views overlooking Michigan’s West Grand Traverse Bay, the Ciccone Vineyard and Winery is where Paula is most often found.
Established by their father Silvio ‘Tony’ Ciccone and his second wife Joan in 1995, it is set across 13 acres and has grown from a family-owned concern into a thriving business, winning awards and operating a popular tasting room. In 2004, when the business was ailing, Madonna stepped in with around £754,000.
It also has a highly regarded sideline as a wedding destination, with couples swapping vows in the vineyard’s quaint 100-year-old barn during the summer months.
‘[Paula is] an intrinsically shy person but she’s forced herself to be less shy because of all the responsibilities she has,’ Michael Schafer, a sommelier, certified wine and spirits expert and member of the board of the Michigan Wine Collaborative, previously told the Daily Mail.
When Madonna dropped out of college in 1978 to go to New York, Paula followed a few years later, staying with her big sister as she attempted to carve out her own showbusiness career.
When Madonna dropped out of college in 1978 to go to New York, Paula followed a few years later, staying with her big sister as she attempted to carve out her own showbusiness career (pictured in 1985)
With short platinum hair, Paula tried out modelling, and took part in an Oprah interview in 1986. She seemed to be uncomfortable with comparisons to her sister, commenting ‘fame changes family’.
While Madonna became an international superstar, Paula had behind-the-scenes jobs in special effects and set costume in film. Both careers fizzled out, however, and Paula moved back to Michigan where she became an artist and then took on a corporate job.
In 2011, Paula was made redundant and spent the summer at the family winery.
‘When I first got here, I just did the website. Then I inventoried all the rows of vineyards for each wine and tagged all of the posts. Once I was done with that, it was ‘What should I do next?’,’ she previously said.
‘I didn’t come up here to be the winemaker, but I thought what the heck, I’ll try it. My father started giving me responsibilities in the cellar, involving me more . . . I started keeping a notebook of all the different procedures.’
Studiously, she improved her knowledge of wine-making with classes at Michigan State University. When Paula’s father passed the baton to her, handing her control of the wine-making process, she began making wine in her own innovative style, and picking up awards.
Gone are the glamorous clothes and high maintenance lifestyle Paula once had as a model. Recently, she cut the ribbon on the winery’s new outdoor seating area, putting aside her dislike of public speaking to thank those involved.
‘I don’t think Paula ever thought she would end up running the family vineyard, but she’s done a great job with it and it’s clearly where she loves to be,’ says Schafer.
There have been bumps in her relationship with Madonna — in 2000, there was bad feeling when Madonna apparently refused to pay for Paula to travel to her second wedding in Scotland to Guy Ritchie. But she has been pictured with other family members at various Madonna tours through the years and the two sisters remain close.
The Ciccone siblings, and their father Silvio, keep a low profile, leaving the limelight to Madge herself. From left: Paula, Madonna, Jennifer and Melanie with their father Silvio Ciccone (sitting) in 2021
‘It’s difficult having a famous sibling and constantly having to contend with someone who is regarded as being better known and more successful than you,’ Gary Johnson, a teacher for 53 years and curator of the Michigan Rock And Roll Legends Hall of Fame, previously said.
He has visited the vineyard several times and describes it as a ‘beautiful, peaceful place.’
‘The two sisters are very different characters but, just as Madonna is a successful businesswoman, so Paula has found her passion and become successful.’
There’s no doubt the two sisters do have something in common, in that they both have a keen business sense and strong work ethic.
‘Paula is a pioneering female winemaker who’s modernised the winery and brought it into the 21st century,’ says Michael Shafer. ‘She’s a talented businesswoman.’
Paula was born in 1959 in Bay City, Michigan. The two girls already had older brothers Anthony and Martin. Christopher and Melanie came along soon after.
Melanie Ciccone: Blissfully married and ‘closest sister’ to Madonna
Madonna’s next sister, Melanie, pictured with husband Joe Henry, is said to be the closest sibling to the star
Madonna’s next sister, Melanie, has previously worked at the family vineyard – and unlike the singer, who has dated a string of partners, Mel is the picture of marital bliss with a husband of 35 years.
Melanie’s passion, however, is to be found in her family. Happily married for more than three decades to the singer and songwriter Joe Henry — the couple have two children.
Like many 60-somethings, they have embraced a quieter life, moving to Maine after 30 years in Los Angeles. There, they enjoy an idyllic existence, coming home to log fires after walks on beaches and in forests. A blissful retirement, it seems, beckons.
Down-to-earth Melanie is said to be Madonna’s closest sister and was the trusted sibling who held her hand when she gave birth to daughter Lourdes.
Often pictured hugging — ‘No one knows better than her what it’s like to survive our toxic and broken family from Michigan,’ the singer once said in tribute to Melanie — Madonna still calls her by her childhood nickname ‘Smells’.
Born in 1962, Melanie studied Spanish literature and language at Michigan State University and was a publicist for Brian Eno’s Opal Records.
Her husband is an old friend of Madonna’s who met his future sister-in-law in 1975 when they were pupils at Rochester Adams High School in Michigan and members of the school’s Thespian Society.
‘[Madonna] was whip-smart and short on patience and, to tell the truth, she scared me more than a little but along with her sister Paula, her presence . . . opened a door through which I would pass and find my life utterly and for ever changed,’ Joe wrote in a 2015 birthday tribute to the pop princess.
Gratitude: Madonna praised her rarely-seen sister Melanie (far right) during her worldwide Madame X tour ahead of her performance in Los Angeles
The pair have collaborated musically on some of Madonna’s hits, but it’s the introduction to Melanie that Joe is most grateful for.
‘There is no other and never has been another,’ he said on the couple’s 35th wedding anniversary. ‘My marriage has been not only the light upon my path but the path itself. Lucky me.’
After devotedly raising her children and working in music, Melanie has built a second career as a fabric artist.
Her talent at quilt making and love of textiles is said to have been inspired by her grandmothers and she has shown her works at the trendy alternative Roswell Space Gallery in Los Angeles.
What she calls ‘the simple materials of everyday life’ make up her creations. One called Un-dress, featuring recycled plastic, bird netting, silk sari rags, thread and measuring tape, was priced at $5,500.
Another called Kind Of Blue, made from fisherman’s rope, printed coffee bags, tulle, butcher paper and thread, was priced at $1,900. She said her work makes her feel purposeful and ‘connected to a deeper sense of herself’.
Jennifer Ciccone: Works on family vineyard but wasn’t invited to sister’s weddings
Jennifer Ciccone is pictured with her mother, Joan, at the family winery in Michigan
Art, and a love of children, again marks the life of the youngest Ciccone sister, Jennifer, who was born in 1967 and closely resembles her blonde mother, Joan.
Choosing a life away from the limelight, she first embarked on a career as an art teacher in Michigan elementary schools, with children aged five to 11.
She married at the family vineyard in 2011, and today works there, and is regarded as an essential member of the management team, along with Paula and her brother Mario who manages the vineyard.
It has been claimed Jennifer wasn’t invited to Madonna’s two weddings and Madonna wasn’t invited to hers.
Yet fences have presumably been mended, since Jennifer has been pictured with other family members at various Madonna concerts over the years. Bespectacled and middle-aged, she too beams in pictures with all the happiness of a life well spent.
Indeed, looking at all the sisters’ faces — last seen side-by-side a few years ago posing happily with their father Tony for his 90th birthday celebrations — it’s almost impossible not to wonder if they show what Madonna would look like if she, perhaps, had taken a more conventional path.
Mario Ciccone: Wild child-turned-vineyard manager
The singer’s brother Mario, seen at the family’s winery in Michigan
Like his older sisters, Madonna’s half-brother and the baby of the family, Mario has also worked at their father’s vineyard.
Perhaps the most private of the family, he previously worked at Madonna’s record company, Maverick. He married in July 2011 and has three children, one from a previous relationship.
Like his brothers, he had a wild period in his youth, taking cocaine and getting into fights. He battered a motorist and broke a police officer’s nose. Madonna paid his legal bills.
***
Read more at DailyMail.co.uk