Celebs You Didn't Realize Have Extremely Troubled Siblings

While many celebrity families produce successful, well-adjusted broods, others are broken and acrimonious—and some are dark and tragic. These celebrities all have siblings that prove sharing a last name and a blood line doesn't mean that they share success, sanity, or even just an ability to obey the law. Here are some black-sheep siblings who can even make their controversial famous brothers and sisters look great by comparison.


The Queen of Pop has a sibling sorely lacking in any royal treatment. Her older brother, Anthony Ciccone, has reportedly been homeless and struggling with substance abuse and legal troubles for years. In April 2013, Anthony was arrested for trespassing in a bookstore with a blood-alcohol level of .40—five times the legal limit in the state of Michigan. The Daily Mail reported that it wasn't the first incident: he was previously arrested for being drunk in a church and swearing in front of children and spent a month in jail. Sources claim Anthony—who alleged that he and Madonna have never loved each other—worked at a vineyard owned by his father and stepmother until they fired him for drinking straight from the vats while on the clock.

A year later, he was still homeless, according to Tablet, and had little hope for the future. "I hesitate to dream because when you dream you get your hopes up. And then you get your heart broke. And so when this happens so many times you hesitate to dream," he said. "I pray for one more chance, but the truth is that there is a good chance I'll never live to witness that day. No one will be surprised if I'll die before my 60th birthday. Neither will I."

Josh Brolin

Josh Brolin's younger brother, Jess, is reportedly homeless and resides on the streets of Ojai, Calif., miles from parents James Brolin and stepmother Barbra Streisand's home in Malibu. According to the Mirror, Jess was evicted from his $800 a month apartment in 2011 and has since refused any help from his mega-successful showbiz family.

A source told the paper, "He will sometimes be sleeping in a field behind shops, basically ­wherever he can bed down. It can be very cold at night as it's in the valley. Looking at him, you wouldn't realize he is part of one of the biggest, most successful showbiz families in the world. It is a heartbreaking situation."

Jess' destitute nature is even more tragic when one recalls that he previously inherited a six-figure trust fund after his mother, James Brolin's first wife, died in a car accident in 1995. Jess reportedly ran out of money around 2011.

A rep for his family said in a statement, "We have offered help and support and we continue to do so. We love him very much and only want what is best for him."

Christopher Nolan

Interstellar (2014) director Christopher Nolan's brother, Matthew, was allegedly part of a terrifying contract-killer plot.

The Daily Mail reported that in 2005, a gem dealer named Robert Breska allegedly hired Matthew to kill Breska's accountant, Robert Cohen, after Breska had £5 million stolen from him. Matthew was accused of using bogus identification and of hiring a hotel bellboy to kidnap, torture, and murder Cohen, allegedly at Breska's behest. The bellboy was eventually convicted of Cohen's kidnapping and murder, but Matthew reportedly high-tailed it back to the United States before Costa Rican authorities could nab him.

Costa Rican authorities sought to extradite Matthew after discovering he'd been seen with the bellboy. At one point, in 2009, he was arrested by the FBI after appearing in court in Chicago for an unrelated bankruptcy case, according to the Chicago Tribune. A judge eventually ruled that Nolan could only be extradited for using a fake British passport, citing insufficient evidence by the Costa Rican authorities, but even that got dropped, according to the Daily Mail.

Insanely enough, while Matthew was being held at Chicago's Metropolitan Correctional Center, he reportedly plotted to escape from prison using 31 feet of rope made from bedsheets, a razor hidden in a mattress, a metal clip that could unlock handcuffs, and a harness. In July 2010, he was reportedly sentenced to 14 months for the escape attempt, but because he'd already served 16 months at the time, he was set free.

Reese Witherspoon

Reese Witherspoon's brother, John Draper Witherspoon, was accused of aggravated burglary and sexual battery in October 2002. People reported that Witherspoon's neighbor accused him of entering her home through an unlocked door when she was asleep and attempting to sexually assault her while she was still drowsy. He was later sentenced to probation for the incident.

Alec Baldwin

Alec Baldwin's less-successful brother, Daniel, calls himself "the drug one" of his famous brood. He admitted to battling drug addiction since 1989, when he first tried cocaine, according to ABC News. Despite attempts to get sober over the years, he's relapsed several times, including an alleged drug-induced "nude rampage" at the Plaza Hotel that sent him to the hospital; and a 2005 injury on the set of Celebrity Fit Club that sent him spiraling into prescription drug addiction.

He went to rehab for the tenth time in 2006, the Mirror reported, and when he was done, he signed up for Celebrity Rehab With Dr. Drew but got booted from the series after just four episodes when it was revealed he was sending "inappropriate" messages to co-star Mary Carey. He told ABC News, "I kid you not, from the first time that I had smoked a hit of cocaine, I was in rehab six months later. It grabbed me so firmly and I was so out of control with it immediately...[I hit my] bottom [and my bottom] has continued to become lower and lower and lower."

Daniel's troubles extend beyond just the health issues associated with drug abuse. He has also faced legal repercussions for his demons. In addition to his 1998 arrest, he was arrested in April 2006 for allegedly threatening a woman, but authorities declined to press charges. In July 2006, he was busted for running a red light and crashing into two parked cars while driving on a suspended license. In November 2006, he was arrested for allegedly stealing a friend's car, but no charges were pursued.

Paris Hilton

You know your family is dysfunctional when Paris Hilton is the most functional member. In February 2015, People reported that Paris' younger brother, Conrad, was arrested after allegedly threatening to kill British Airway flight attendants and calling fellow passengers on a flight "peasants."

Conrad—who has reportedly been involved in multiple and scary car crashes over the years—was accused of "assaulting and intimidating the crew to the point where it interfered with their ability to perform their duties," making children cry and smoking cigarettes and marijuana in the airplane bathroom. When Conrad fell asleep during the flight, crew members restrained him by handcuffing him to his seat.

According to TMZ, Conrad also told crew members, "I could get you all fired in five minutes. I know your boss! My father will pay this out. He has done it before. Dad paid $300K last time." After the incident, Conrad—whose lawyer claimed his outbursts were an adverse reaction to a sleeping pill—checked into rehab and was later sentenced to three years of probation and 750 hours of community service.

Later that year, Conrad's troubles continued when he was arrested for allegedly trying to break into ex-girlfriend Hunter Salomon's home. He was allegedly so out of control during the incident that his father, Rick Hilton, had to help police subdue him.

The following year, things got even worse for Conrad when he was sentenced to two months in prison for testing positive for drugs three separate times in violation of his parole from the flight incident. He was released in August 2016, but troubles continued: TMZ reported that Conrad was sued after he got into a head-on collision with another driver...when he was prohibited from driving.

Hayden Christensen

Actor Hayden Christensen's brother, producer Tove Christensen, was involved in a scary incident in 2009. TMZ reported that Tove was arrested for assault with a deadly weapon after he allegedly got into a physical altercation with his girlfriend. He allegedly pushed her down and got into his car. When she reached into the vehicle to grab her purse, he allegedly put the pedal to the metal, dragging her down the street for 30 feet. Sources told TMZ that when police arrived, Tove's girlfriend had visible marks on her arms from the incident. He was eventually sentenced to community service, one year of domestic violence counseling, and three years of probation after pleading no contest to misdemeanor battery.

Mariah Carey

While Mariah Carey is showing off her vocal range and continuing her reign as the Queen of Christmas, her sister, Alison, hasn't fared nearly as well. In 2005, Alison was busted twice for prostitution, which the New York Post alleges had been her profession since the 1980s to support a drug habit.

"With everyone in the family being as aware of Alison's problem for as long as it has been, this was bound to happen," an insider told the Post. "At this stage, most everyone else in the family has had it with Alison, but Mariah isn't one to give up on people. Unfortunately, Mariah is having to learn that you can't help someone who doesn't want to be helped." The source also added that at the time, Alison had been in rehab at least 10 times, with most of her stints on Mariah's dime. "Mariah, especially, wanted a reconciliation. She thought it was important to try and have something good come out of an awful situation," the insider said.

In March 2016, Mariah and Alison's brother, Morgan, told the Daily Mail that Alison, who is HIV-positive, suffered severe brain damage and needed several surgeries after a home invasion left her injured and physically and mentally ill. "Alison was institutionalized for observation after being found wandering in the street barefoot and partially dressed, causing the police to be concerned," Morgan said. "Her behavior was caused as a result of damage done in the attack and her having missed the medications she was taking. Because Mariah has not found it in her heart to help Alison get the care she requires, there are times when Alison forgets or is unable to take her medication and this sometimes precipitates problematic behavior."

Though Morgan makes it seem like Mimi is uncaring and insensitive, the singer's rep says that's not true. "Through the years, Mariah has spent hundreds of thousands of dollars supporting Alison and her children," Carey's rep said. "In fact, Mariah has supported her extended family for over two decades."

Alison's troubles have continued: Us Weekly reported that Alison was arrested for prostitution yet again in August 2016, even using Mariah's lyrics to "Fantasy" to advertise her services online.


Prince's sister, Tyka Nelson, led a troubled life until her famous brother helped her out. Nelson reportedly prostituted herself to support both her children and her own crack cocaine addiction. "I was a single mother and my boys were babies. I sold my body for food, money and pampers," she told the National Enquirer in 2003 (via People). "I pawned the car Prince had given me and sold the kids' TV for drugs." Thankfully, Prince sent Nelson to rehab, and she's reportedly been clean, sober, and healthy ever since.

Dane Cook

Comedian Dane Cook's brother, Darryl McCauley, was the funnyman's manager for years. Unfortunately, he was grossly dishonest the entire time. CNN reported that in 2010, McCauley and his wife, Erika, were found guilty of stealing $12 million from Cook when they were supposed to be managing his businesses. An investigation was launched on McCauley and Erika in December 2008, when Cook alerted authorities to millions of dollars missing from his business accounts. McCauley was sentenced to six years in prison and 16 years of probation while Erika was sentenced to three years of prison and 13 years of probation. They were ordered to repay Cook the money they'd stolen, according to the report.

Nick Cannon

In March 2011, Nick Cannon's brother, Gabriel, was arrested on suspicion of robbery and assault. E! News reported that Gabriel was allegedly in a group of four men who assaulted production company workers Alex Moreno and his 17-year-old son, Alejo, after a business meeting went horribly wrong. Gabriel and his cohorts then allegedly stole jewelry and video recordings from the father and son. The group's arrest was reportedly caught on video.

Gordon Ramsay

Gordon Ramsay's brother, Ronnie, is often in hot water, though never in a kitchen. The Daily Mail reported that Ronnie has struggled with heroin addiction and homelessness—and that Ramsay admits to even buying Ronnie heroin in 1997 to get him through their father's funeral. After Ronnie was jailed in Indonesia on drug offenses in 2007, Ramsay reportedly refused to enable him anymore.

The Kitchen Nightmares star told the Mirror in November 2014, "I have tried to help many times. It's hard. Every time you see him, God bless him, it reopens a wound for everybody," he said. "Like any addict they live for the day and each day is a challenge. Sometimes you have got to be a little bit stronger than the previous time and introduce tough love." He added, "They have got to hit rock bottom before they want to get out of that scenario, so I think it is more painful from the outside for mum...We always clash and it is hard to get back to that ground zero."

Kathy Griffin

Kathy Griffin opened up in 2009 about her deceased brother Kenny, who she claimed was a pedophile. "My brother Kenny, who is now passed away, was a pedophile and went to prison and obviously wreaked a lot of havoc on my parents and the family," she told Entertainment Tonight (via Movieline). "When you grow up in a house with someone with that, I don't know if you call it energy, but he was violent. I saw him beat his wife right in front of me. "You know, he was a pedophile. He was extremely sexually inappropriate with me ever since I was a teeny kid," she continued. "It kind of shapes the way you see the world. For me, it is definitely tied into my trust issues I have with guys...In a way, it maybe even contributed to me having a really dark sense of humor."

Terrence Howard

Terrence Howard has a lot of legal issues of his own, but he's not the only problem child in his family: his brother, Antonio, has had two significant run-ins with the law.

The Times Herald reports that in February of 2011, police responded to a domestic disturbance call at Antonio's home. When they arrived, Antonio threatened the officers with his 100-pound dog. He ended up pleading guilty to three counts each of terroristic threats and reckless endangerment, along with one count of ethnic intimidation. At the time of his arrest, Antonio was on probation for a DUI charge.

Unfortunately, it wasn't the only incident involving Antonio and his dog. Philly Mag reports that in 2015, police shot Antonio's "very aggressive" dog, which at that point weighed close to 170 pounds. The dog had been seen wandering around a neighborhood unattended and frightening residents, and wouldn't be contained with a taser or other methods.

Leonardo DiCaprio

Leonardo DiCaprio's stepbrother, Adam Farrar, was on the run from police in March 2016 after skipping a court date for petty theft, the Sun reported. Farrar, who reportedly piqued DiCaprio's interest in acting through his own roles in commercials and TV shows such as Galactica (1980) and Eight is Enough (1977), allegedly stole around $990 worth of merchandise in January and skipped a court date for the offense.

A source told the Sun, "[Farrar] continues to run away from responsibilities and it's going to land him in jail again. He's struggled before with drugs and although he makes promises to get clean, he gets caught up in something else. Leo is sympathetic but this is the latest in a long line of offenses and he's at the end of his tether."

In November 2016, Farrar told the Daily Mail, "[DiCaprio and I] were once so close. I loved him and I still do. But we've not spoken in a couple of years." He added, "I was arrested five or six times for petty theft, shoplifting from supermarkets, trying to support an opiate addiction of half a gram to a gram a day. Leo and I never had an argument. But he started surrounding himself with people that didn't want me around. He's the biggest star in the world and there's me, messed up on drugs. I was slowly shut out of his world. Finally I got tired of going in and out of jail. I've been off heroin since 2013."

Nicki Minaj

Nicki Minaj's older brother, Jelani Maraj, was charged with first-degree rape of and first-degree sexual conduct against a 12-year-old girl in December 2015. Page Six reported that Minaj bailed her brother out of jail—his bond was set at $100,000. At the time of this writing, Maraj maintained had maintained his innocence, rejected a plea deal, and his trial was pending. The New York Daily News reported that Maraj faces life in prison if convicted.