From Madonna's brother to Mariah Carey's sister, some celebs have very troubled siblings
Celebrities and their net worths barely fail to amaze fans. However, having a celebrity family member isn't a sure shot method for a comfortable life, an example of this is the disparity between the lives of the rich within Hollywood and their not-so-fortunate siblings. In the last week of September, Cheryl Tweedy's brother Andrew was revealed to be living in tents and getting by on handouts after he split from his girlfriend. “I’ve been begging here for more than three months and it’s something that has really broken my heart,” he said despite Cheryl shelling out $23,165 to help rehabilitate him in the past.
According to the Sun, Andrew has a long history of violent crimes but he's not the lone celeb sibling to have gone off the rails. Meghan Markle's highly publicized feud with her brother and father keeps making headlines time after time. Similarly, Mariah Carey's difficult relationship with her sister Alison, who was arrested from a New York hotel for prostitution in 2016, has been widely covered in the media. However, there are some celebrities and their sticky situation with their siblings that you might've missed hearing about. Continue reading below for a list of the rich and famous whose siblings are barely managing to get through life.
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Celebrities with extremely troubled siblings
Paris Hilton's brother Conrad Hilton
From taking his ex-girlfriend's father's Bentley for which he was charged with a felony to being ordered to attend mental health and substance abuse counseling - Paris Hilton's brother Conrad has seen it all. Conrad's ex also sought out a restraining order against him for trying to contact her. Conrad's brush-ins with the law have been plenty. Right from leading an officer on a high-speed pursuit in May 2015 where he ended up crashing his Black BMW to being arrested on suspicion of violating a restraining order in June 2015, after being found inside his ex-girlfriend's house - Conrad didn't stop. A year later, he found himself in jail for two months after admitting to using pot, cocaine, and synthetic marijuana.
Madonna's elder brother Anthony Ciccone
A decent number of people might have seen Madonna's brother Anthony Ciccone's photo with stitches running across his face. His forehead was required to be sewn up after he resisted being arrested in a public bathroom in northern Michigan back in 2013. Police were called to the facility after he refused to leave the bathroom at the Grand Traverse County Civic Center. His blood-alcohol level at the time of arrest was 0.40, the legal limit for driving is 0.40. He was resisting arrest and was brought to the ground by an officer after which he hit his head on the ground.
At one point in 2013, Ciccone accused Madonna of not caring if he was dead or alive. He reportedly was fired from his job on the family vineyard after passing out after drinking from the vats. He then started sleeping under a Michigan bridge, battling -30c temperatures. “Madonna doesn’t give a s**t if I’m dead or alive. She lives in her own world. I never loved her in the first place, she never loved me. We never loved each other,” he said in 2013. He was back with his family sometime in 2017 after Ciccone sought treatment from a rehab facility for homeless addicts. He was reportedly back home and recovering later.
Reese Witherspoon's elder brother John Draper Witherspoon
John Draper Witherspoon was accused of aggravated burglary and sexual battery in October 2002. His neighbor in Nashville had accused him of entering her home through an unlocked door when she was sleeping and that he violated her modesty while she was still not completely woken up. John, an alcoholic working on rehabilitating himself at the time had received probation for the incident. Contrary to other stories where siblings are heard of cutting ties with their problematic family members, Reese stayed close to her brother and in April 2021, she shared a photo with John in honor of National Siblings Day.
"My Brother John taught me so much about how to explore the world. As kids, we were always exploring and looking for new adventures. Wherever we were, whether it was in the woods or at a gocart track or white water rafting, he encouraged me to be strong & fearless. My biggest supporter and cheering section since Day one. I love you, Big Bro!" she wrote.
Gordon Ramsay's brother Ronnie Ramsay
Chef extraordinaire and TV host Gordon Ramsay is known for being a tough cookie to crack. In a rare display of vulnerability, Ramsay spoke about how he failed while trying to help his brother Ronnie beat his lifelong addiction to drugs. Ronnie has been on drugs from the time he was a teenager and he's lived his life on the streets and has experienced homelessness quite a lot in life. His drug habit took him to jail after being arrested in Indonesia where he reportedly was caught for selling heroin. In a 2017 documentary, Ramsay said watching his brother struggle throughout life because of drugs changed his attitude towards substance use early on.
"I have been very anti-drugs from very early on in my life, having to watch my brother f*** his life up going from coke to heroin," Ramsay said further adding he had to score drugs for Ronnie to get him to attend their father's funeral. "I went to a dealer's house once and I had to take my little brother to a s***hole of a flat to get a fix to get him to our father's funeral. That was f***ing grim, and that was a big shock for me to see how far he had gone."
Rapper David Omoregie aka Dave's brother
Mercury Prize winner in 2020 for his debut album 'Psychodrama' in 2020 to appearing on Netflix's 'Top Boy', Dave had everything going for him. His brother Christopher Omoregie had been in the news too, a decade ago when he was 18, for the brutal stabbing of Sofyen Belamouadden, 15, in London's Victoria Station in 2010, an attack which was described as "ferocious and merciless" and involved 20 teenagers who stabbed the boy nine times. Omoregie was convicted for murder and sentenced to a minimum of 18 years.