Madonna is one of the most successful musicians of all time, amassing a net worth of more than $850 million during a decades-long career. But while the singer has lead a glamorous life filled with star-studded parties, designer clothing, lavish vacations, and VIP treatment, her older brother, Anthony Ciccone, had a very different story.
He battled alcoholism and homelessness for years, facing numerous run-ins with the law, and fighting to stay alive as he slept on the streets with nothing but a sleeping bag to protect him from the freezing cold winters.
The startling contrast between Anthony's life and his sister’s inevitably raised the question: how could a woman with millions of dollars in her bank account leave her brother in such desperate straits?
It also left Anthony fiercely bitter - and he continuously slammed his famous sister for 'turning her back on him' while he was having a 'hard time,' and claimed she 'never loved him' and didn't give 'a flying f**k' about him in a series of scathing interviews over the years.
Anthony and Madonna's relationship was complex to say the least - and it has now seen a tragic ending as it was announced over the weekend that Anthony had passed away at age 66.
Madonna's older brother, Anthony Ciccone (seen in 2011), has died at age 66. He battled alcoholism and homelessness for years and faced numerous run-ins with the law
The sister-brother duo were born just two years apart and grew up with their Catholic parents and four other siblings in a suburb of Detroit, Michigan.
However, Anthony once said that he and Madonna 'hated each other' from a young age, due to immense 'sibling rivalry.'
The family faced heartbreak when their mother died from cancer when Madonna was only five and Anthony was just seven - which the singer later described her passing as the 'motivating force' behind her descent to superstardom.
His mother’s untimely passing had just as much of an impact on Anthony - but instead of driving him onwards like it did for Madonna, it blighted his life and lead to a severely different path.
As Anthony sadly passes away, FEMAIL has taken a look back into his difficult journey - as well as his complicated relationship with his sister Madonna (seen in 2016)
In his 20s, he dropped out of college and spent years struggling to hold a job. He moved all around the country working odd positions - but when his girlfriend became pregnant in 1993, Anthony thought it was his chance to turn things around.
However, it did just the opposite. When they ultimately split six years later, and he was told he wouldn't be allowed to see his son it drove him 'insane,' sending him into a downward spiral of heavy drinking.
He soon found himself with no job, no money, and nowhere to live. His relationship with his family became fractured, thanks, in part, to his continued interviews with the press, in which he ferociously slammed them for their lack of support.
He was forced to sleep under a bridge in Michigan and huddle in the lobby of the local jail to get warm - a dreadful contrast to his younger sister's ascension into the celebrity heavens.
And while Anthony has insisted that his family left him with nothing, it seemed like they tried on multiple occasions to help him turn his life around - and rather, his inability to admit that he had a problem was what lead to things falling apart.
Madonna offered to pay for rehab for him on multiple occasions - but he insisted he didn't need professional help - and his dad employed him at his winery for several years, before he had to fire him after his drinking started to interfere with his work.
Anthony finally agreed to seek treatment for his alcoholism in 2017, and it was said that he reconnected with his parents in his final years, however, it's unknown where his relationship with Madonna stood.
As Anthony sadly passes away, FEMAIL has taken a look back into his difficult journey - as well as his complicated relationship with his sister Madonna.
Growing up together in a suburb of Detroit, Madonna and Anthony had fierce 'sibling rivalry' from the start - and faced heartbreak when their mom died of cancer, which 'motivated' her to become a star but lead to a downward spiral for Anthony
Madonna and Anthony were born to a car engineer designer, named Tony, and a stay-at-home mother, also named Madonna. Madonna is seen with her dad on his 90th birthday
Madonna and Anthony were born to a car engineer designer, named Tony, and a stay-at-home mother, also named Madonna.
The brother-sister duo - who also had four other siblings: two brothers, named Martin and Christopher, and two sisters, named Paula and Melanie - were only two years apart in age, but from the start, it seemed as though they were worlds apart.
Anthony once said that he and Madonna 'hated each other' from a young age, due to immense 'sibling rivalry.' They grew up in a suburb of Detroit, Michigan, with their four other siblings. Madonna is seen as a teen
As kids, Anthony told DailyMail.com in a 2011 interview that he and his sister didn't get along well due to 'sibling rivalry.'
'We hated each other - sibling rivalry, I imagine,' he said. 'She was a b***h, just like she is now. She remains true to form. You have to give her credit for consistency.'
He explained that she was a troublemaker from a young age, which made things difficult for him as the eldest sibling in the family.
'She’d sneak guys into the house when my father wasn't around and I was supposed to be responsible for us all,' he recalled.
'She’d be in the bedroom with some guy, and my little brothers and sisters would be standing outside with their ears cupped to the door, listening.
'I’d have to bust the door open and kick the guy out. She didn’t forgive me for that. To me, she was just an annoying sister.'
The family grew up in a suburb of Detroit, Michigan, called Pontiac and Avon Township, but they faced heartbreak in 1963, when their mother died of breast cancer when Madonna was only five and Anthony was just seven.
The family faced heartbreak when their mother died from cancer when Madonna was only five and Anthony was just seven. Madonna is seen in 1972, at age 14
After that, Madonna and Anthony's father got re-married to the family's housekeeper, named Joan Gustafson, in 1966, and they went on to have two more children together - a daughter named Jennifer and a son named Mario.
Losing her mother effected Madonna greatly, with her later telling Interview magazine that it became the 'motivating force' for her finding success as a singer.
'I became very obsessed with death, and the idea that you never know when death will arrive, so one has to do as much as possible all the time to get the most out of life. That would be a motivating force,' she explained.
She added to Rolling Stone: 'I've turned my need on to the world and said, "OK, I don't have a mother to love me, I’m going to make the world love me."'
His mother’s untimely passing had just as much of an impact on Anthony - but instead of driving him onwards like it did for Madonna, it blighted his life and lead to a downward spiral, a dreadful contrast to his younger sister's ascension into the celebrity heavens.
Anthony dropped out of college and spent years struggling to hold a job while his sister shot to superstardom - but his life fell apart after he turned to alcohol to numb the pain of losing his son and girlfriend
As his sister was being propelled into the spotlight during the '80s, Anthony was working a series of odd jobs that saw him moving all around the country
In 1978, Madonna and Anthony went their separate ways when she moved to New York to pursue her dreams of being a musician, while he stayed in Michigan.
As his sister was being propelled into the spotlight during the '80s, Anthony was working a series of odd jobs that saw him moving all around the country.
After dropping out of college, he worked as a film location scout in New York, he canned salmon in Alaska, tuned pianos at a Michigan school, and served as a set carpenter in Los Angeles.
He also spent five years working for the controversial Unification Church of the Reverend Sun Myung Moon in San Francisco, after he was brought into the organization by his girlfriend at the time.
Anthony and Madonna's relationship dissolved as their lives went in opposite directions, however, their paths did briefly cross again when he moved back to New York in his 30s to work as a photographer's assistant.
He told DailyMail.com that he and his sister - who was already a huge star by that point - would party together in the Big Apple, alongside a slew of other famous faces.
He recalled once sharing a joint with Mick Jagger as they sat around a New York nightclub table with his sister, David Bowie and Iggy Pop.
He also remembered one time when he and Van Halen rocker David Lee Roth spent a 'bemused' night wandering about 'looking at the freaks' during a bondage-themed party that Madonna had thrown.
'Mick was cool, Iggy was cool, David Bowie was kind of cold,' he revealed.
Anthony spent the early years of his adulthood with no real career path and struggling to hold a job longer, but when he welcomed a son, named Angelo, in 1993, with his girlfriend at the time - a costume designer named Mary Jane Lawson - he thought becoming a father would help him turn his life around.
Anthony welcomed a son in 1993, but when he and his girlfriend at the time split and he was told he couldn't see his son, it sent him into a downward spiral. He is seen in 2011 However, it did just the opposite. He and Mary split six years later, in 1999, and after going their separate ways, she stuck Anthony with a restraining order and accused him of threatening her - something he denied during his interview with DailyMail.com in 2011.
At the time, he said he hadn't seen his son in 10 years and explained that losing Angelo and Mary made him go 'insane.'
He soon started struggling with alcoholism, which resulted in him losing his job, followed by his home.
Things hit an all time low for Anthony, and he spent two years living on the streets in downtown Los Angeles, which he described as 'a descent into Hades.'
'When I became a father, I thought I was impervious. All I wanted was to be with the woman I loved and my child,' he explained. 'They were all I ever really wanted.
'I went from being a full-time family man with no experience on the street to living in crackland - a white guy in a sea of African-American crackheads.'
However, after going to rehab - he spent two months at a clinic in Houston, Texas, which was paid for by Madonna - things seemed like they were looking up for Anthony.
His dad offered him a job at his family's winery, called Ciccone Vineyard, back in Michigan, where he worked for several years, picking grapes, planting vines, and sampling the products.
But when he started drinking heavily again, his dad fired him - and he found himself living on the streets once more, all while his sister continued to soar to superstardom.
Anthony then found himself living on the streets, sleeping under a bridge, and struggling to find food, while getting by off the money he'd earn from collecting empty cans and bottles
Anthony spent years fighting to stay alive as he slept on the streets with nothing but a sleeping bag to protect him from the freezing cold winters. He is seen in 2011
In an explosive interview with The Michigan Messenger in the fall of 2011, Anthony detailed his downward spiral.
At the time, he said he spent most of his nights sleeping under a bridge in the northern ski town of Traverse City, while battling frostbite - his only shelter was a sleeping bag - and severe loneliness - his sole companion was another street dweller named Michael.
To get warm, he said he would sometimes huddle in the lobby of the local jail. As for food, he explained that he was getting most of his meals from soup kitchens and churches, and claimed that he earned roughly $10 a day from collecting empty cans and bottles.
All the while, Madonna's career flourished. And the startling contrast between Anthony's life and his sister’s inevitably raised the question: how could a woman with a $650 million fortune leave her brother in such desperate straits? She is seen in 2009
'I don’t have any income. I’ve got to go collect bottles and cans, do odd jobs,' he explained.
'If you spend enough time on frozen concrete without proper insulation you will get frostbite. You have no idea how gruesome it is.
'You get nerve damage. That’s the milder stage, in the severe stage you have tissue damage, that is when you lose parts of your body. A friend of mine lost all ten toes. Several have died of hypothermia.'
He spoke about his rough life further to DailyMail.com that same month, explaining that he was often beat up by other homeless people, and that he had sustained several broken bones in his face and shoulder, as well as shattered teeth.
He said he often feared for his life, and that he and his friend Michael had to take turns keeping watch while the other one slept.
When asked about the possibility of going back to rehab at the time, Anthony seemed uninterested, calling it 'boring' and insisted that he didn't need any professional help.
Anthony became fiercely bitter that Madonna 'turned her back on him' while he was having a 'hard time' - and claimed she 'never loved him' and didn't give 'a flying f**k' about him in a series of scathing interviews
It also left Anthony fiercely bitter - and he continuously slammed his famous sister for 'turning her back on him' while he was having a 'hard time.' He is pictured in 2011
The startling contrast between Anthony's life and his sister’s inevitably raised the question: how could a woman with a then-$650 million fortune leave her brother in such desperate straits?
At the time, the Material Girl owned six expensive houses in London alone, while just about everything Anthony owned could fit into the plastic shopping bag he carried around with him.
And it was clear that Anthony was fiercely bitter about it. While speaking to The Michigan Messenger, he slammed Madonna for 'turning her back on him' while he was 'having a hard time.'
'You think I haven't answered this kind of question a bazillion times - why my sister is a multi-bazillionarie, and I'm homeless on the street?' he scathed.
'Never say never. This could happen to anybody. My family turned their back on me, basically, when I was having a hard time.'
While he did say he was 'proud' of how far his sister had come to DailyMail.com, he blasted her once again for not having 'more family loyalty.'
'My sister’s a multi-millionaire - she earned it, I have to give her credit for that - but you’d think there’d be some more family loyalty, and that’s not the case,' he said.
'There isn’t much else that exists outside of what she’s doing. I’m a zero in [my family's] eyes, a non-person, an embarrassment.
'If I froze to death, my family probably wouldn’t know or care about it for six months.'
Anthony branded Madonna as a 'terrible actress' at the time, and said he had little time for her music, but added, 'She’s a great entertainer and an excellent businesswoman.'
He also called her fame a 'burden' to him because he said he felt like people treated him differently for being relate to the musician.
'I can’t be me, I have to be related to a celebrity,' he explained. 'People have their ideas and expectations.'
He added in a separate interview: 'I get chased around by freaks, it happens everyday. Crazy people chase me around, because my sister’s famous.
In 2013, Anthony said he and Madonna 'never loved each other' in a scathing interview, adding, 'We were never friends.' She is seen with her other brother Christopher
'I’ve had a few collisions with drunken fools, who decided my face didn’t look pretty enough so they needed to rearrange it.'
By that point, he said they had no relationship, and that the last time he saw his sister was when she was stepping out of a luxury limousine at a film festival in Michigan three years prior.
He watched on from a distance in the gathering crowd, as flashing camera bulbs and screaming fans greeted her.
In 2012, Anthony also hitchhiked to the Super Bowl in Indianapolis where his sister was performing at the half time show.
He said he heard her perform from the parking lot, where he sat drinking beer with his fellow vagrants.
He told DailyMail in a 2013 interview: 'They wouldn’t let us in we didn’t have tickets. We sat in the parking lot drinking beer. I don’t think she would have given a flying f**k that I was out there.'
At the time, he insisted that he and Madonna 'never loved each other,' adding, 'She don’t owe me nothing. That’s her s**t man, she made her money, she worked for it.
'If she wants to live that way, that’s her thing. We were never friends anyway. When we were growing up we were enemies.'
He also said his family was 'against him' and that he didn't want anything from them except 'love and care.'
While Anthony insisted at the time that his dad 'would be happy if he died of hypothermia' since he 'wouldn't have to worry about him anymore,' a family friend who worked at the family's vineyard told a different story.
'He doesn’t want to be bothered, he’s lived his life. He doesn’t like me,' Anthony told DailyMail.com about his father at the time.
'He doesn’t want me to be me, he wants me to be somebody else. He thinks the way I live is intentional. He simply doesn’t know me.'
However, Kathy Meteyer claimed that Anthony's parents were terrified that he might die due to his substance abuse, but added that they refused to take him back until he cleaned up his act and quit drinking.
She insisted that they tried to help Anthony - and that they even tried to bring him a plate of food on Thanksgiving - but said he was the one who had turned them away.
Anthony faced numerous run-ins with the law, and was jailed for trespassing, resisting arrest, and getting drunk in a church and swearing at children as he continued to struggle with alcoholism and homelessness
Anthony had his fair share of run-ins with the law. He was arrested in 2013 in Michigan after getting into a nasty brawl with a police officer, which resulted in him needing nine stitches
Anthony had his fair share of run-ins with the law. He was arrested in 2013 in Michigan after getting into a nasty brawl with a police officer, which resulted in him needing nine stitches.
At the time, it was reported that law enforcement officials were called to the Grand Traverse County Civic Center after Anthony refused to leave the bathroom.
Police said a female officer attempted to arrest him on an outstanding warrant for trespass, but he started to resist.
A then-56-year-old unruly Anthony confronted the responding officer in an aggressive manner, so she then took him down, which resulted in him smashing his face against the bathroom floor and needing several stitches.
At the time of his arrest, his blood-alcohol level was 0.40, which was five times the legal limit.
According to authorities, the warrant stemmed from a March incident when Anthony refused to leave a bookstore.
He also spent a month in jail after he was arrested for getting drunk in a church and swearing in front of children.
'Someone took offence because I used some strong language in a public church,' he told DailyMail.com of the incident.
'I was having an argument with a person who disagreed with me and I was trying to call him down but he didn’t listen.'
'I had never been arrested or had a brush with the law in my entire life until I came here to this town.'
Anthony turned his life around in his final years, after finally agreeing to go to rehab and reuniting with his family after seven years of homelessness - before he passed away this week at age 66
In 2017 - after living on the streets for seven years - it was reported that Anthony had turned his life around after going to rehab. It's unclear where his relationship with Madonna (seen) stood
In 2017 - after living on the streets for seven years - it was reported that Anthony had reconnected with his family after finally agreeing to receive professional help.
His brother Christopher told the Mirror at the time that he had made strides at a rehab facility and that he was finally 'back home, recovering' with his family.
Michigan treatment center Dann's House confirmed his stay, telling the outlet: 'Anthony loved it at Dann's House for quite a while, and made significant improvements in his life while he was with us.'
Joe Henry, the husband of his sister Melanie, confirmed Anthony's passing on Sunday, stating, '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. 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.'
Following the news of his death, a former girlfriend named Carolina Gengo - who dated him in his 30s while he was living in New York - also shared a tribute to him and described him as a 'positive light.'
'He was a lost soul trying to find his way but he was a good person,' she said. 'He had books everywhere, that was all he really had.
'He was into reading about life and philosophy. And he wanted to sit around and talk about it.'
She also said he 'didn't like being known as the brother of Madonna,' and 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.
At the time of his death, it was unclear where his relationship with Madonna stood.
ncG1vNJzZmivp6x7pa3IpbCmmZmhe6S7ja6iaJ6Voq6quI6aqa2hk6Gybn2QcHBxa2hmfI6tw6ilp5mjYq%2Bzu9OhnKtlcaPBqbvNsmR8oZOYvK%2BxjJ2gnqtde7yzucSrZJqkk6S1sLjInGShp52auaa%2F0maamqqVmr9uv86aqZ6cXp3Brrg%3D