20. Chet Hanks
The second son of Tom Hanks and Rita Wilson, Chet Hanks has never been shy about his struggle with drug addiction and alcoholism. In 2015, he ended up in an accident where he rear-ended a vehicle while under the influence, which ended up with him checking into rehab. Despite his parents coming to his aid, Chet blames them for his situation, believing they shouldn’t have let him own a car with his struggles with sobriety.
19. Weston Cage
Weston Cage is the son of actor Nicolas Cage who has been in and out of rehab for drug abuse. In 2011, he was arrested for domestic violence and just can’t seem to keep himself out of trouble. No wonder Nicolas Cage looks like he’s aged 30 years in the last decade. Kids these days, right?
18. Indio Downey
It’s no secret that Robert Downey Jr. suffered from drug addiction in the past and it seems that has been passed down to his son. Back in 2014, his son Indio Downey was caught with cocaine and charged with a felony count of possession. Refusing to let his son follow down the same dark path, Robert sent his son to rehab. Good for you dad!
17. Bobbi Kristina Brown
Whitney Houston and Bobby Brown both struggled with substance abuse for many years, which resulted in Whitney Houston’s death in 2008. Four years later, after her own struggle with substance abuse, Bobbi was found unresponsive in a bathtub. After spending weeks in a coma, she passed away in 2012.
16. Jaycee Chan
Jackie Chan was named an anti-drugs ambassador for the Chinese government in 2009, so imagine his embarrassment when his son Jaycee was caught up in a drug bust in 2015 and sentenced to six months in prison. Yep, you read that right…Jaycee Chan was caught with over 100 grams of marijuana. Yikes.
15. Scout Willis
It seems Bruce Willis and Demi Moore’s daughter, Scout is taking after her parents’ wild ways because she seems to think run-ins with cops are a good time. It seems trying to pass off a fake ID to a cop landed her in jail. Definitely not the best course of judgment, right?
14. Marcus Jordan
Marcus Jordan, son of the famous Michael Jordan, seems to be nothing but trouble. He has been arrested on multiple occasions for disorderly conduct and has also shared photos of his genitals on Twitter. It seems he has no shame, we can’t imagine Papa Jordan is impressed.
13. Cameron Douglas
Cameron Douglas, son to Michael Douglas, seems to be on a path of total destruction. Arrested for multiple drug offenses, he was sentenced to 5 years in prison in 2010 for selling drugs out of a Manhattan hotel. Unfortunately, prison proved to be too much for the young Douglas where he violated the rules and tried to smuggle drugs in jail. This landed him in solitary confinement for two years. He is scheduled to be released sometime in 2018.
12. Marston Hefner
Hugh Hefner’s youngest son, Marston Hefner has gotten himself into quite a bit of trouble in the past. He was arrested in 2012 for beating his Playmate girlfriend, Claire Sinclair and was sentenced to 52 weeks in a domestic violence program. He’s also been charged with vandalism in the past. Hopefully, he cools his jets now that his father has passed away.
11. Nicole Richie
Nicole Richie is the famous daughter of even more famous Lionel Richie. While she’s best known for her hit reality show “The Simple Life,” Nicole has also had a bit of a rough past. She was charged with possession of heroin in 2003 and was convicted of a DUI in 2006. Thankfully, now that she is a mother, she seems to have calmed herself down.
10. Charlie Sheen
Charlie Sheen is best known for his role in “Two and a Half Men” as well as being the son of Martin Sheen. The textbook definition of a problem child, Charlie has been in and out of rehab for decades, struggled with drug addiction and even dealt with battery charges. He even was fired from his television show.
9. Jenna Bush
You would think the daughter of former President George W. Bush would be a little angel, but Jenna Bush seems to have a wild side. In 2001, she was arrested for underage drinking in Texas. We’re sure daddy was so proud of that moment.
8. Christian Brando
Son of the late Marlon Brando, Christian Brando was convicted of killing his sister’s boyfriend in 1990. He spent six years in prison but later was charged with spousal abuse by his ex-wife. Sadly, after the rocky life he lived, Christian died in 2008 from pneumonia.
7. Kelly Osbourne
Kelly Osbourne’s struggles with drugs and alcohol have been highly publicized her entire young adult life. She’s also been arrested for assault and struggled with weight gain. It seems she may have inherited her dad’s wild ways.
6. John Carter Cash
The son of music legend Johnny Cash has proven to be no angel. Arrested after a hunting trip in Newfoundland back in 2014, he was stripped to his underwear while acting drunk and disorderly. Apparently, this isn’t the first time he’s been caught with his pants down either. His father must be rolling over in his grave.
5. Nick Hogan
Nick Hogan, son of Hulk Hogan, has had a rocky young adult life. Struggling with alcohol and substance abuse, Hogan caused a terrible crash in 2007, which resulted in the passenger he was with needing full-time care due to a serious brain injury. Charged with a felony DUI, Hogan has definitely struggled since then.
4. Theodora Richards
It seems the apple doesn’t fall too far from the tree when it comes to Keith Richard’s daughter, Theodora. Not only has she been caught with marijuana and other controlled substances, but she was caught spraying graffiti on a convent. One has to wonder what nun pissed her off?
3. Caroline Giuliani
You have to wonder if the pressure of being the daughter of a major political figure like Rudy Giuliani is the reason good girls go bad. Caroline hasn’t been the daughter of the year that’s for sure. She was arrested for a misdemeanor shoplifting charge in 2010. You’d think being Giuliani’s daughter she’d have access to an endless supply of cash?
2. Nate Montana
The son of famous quarterback Joe Montana, Nate Montana has been nothing but trouble for the former football star. Not only was he arrested in 2011 for a DUI, but he’s also been charged with a misdemeanor for underage drinking while attending Notre Dame. Maybe it’s time Joe tackles this issue before his son continues on this path of destruction.
1. Richard Hilfiger
Richard Hilfiger is the son of famous designer, Tommy Hilfiger and we have a feeling he’s most likely not inheriting the family fortune. A wannabe rapper who goes by the stage name of “Rich Hill,” he was arrested in 2010 for marijuana possession with the intent to sell. While he did post his own bond, we can’t imagine Papa Hilfiger was too amused.