Top 10 Celebs Whose Parents Are Criminals

While Lindsay Lohan’s legal issues have often been the subject of headlines, she isn’t the only person in her family to struggle with the law. Her father Michael Lohan was a Wall Street trader working in commodities exchange. Back in 1990, Lohan was convicted of insider trading and spent three years in prison after getting convicted of criminal contempt of court. It wouldn’t be the last time he went behind bars. He was sent to prison on numerous occasions thereafter, for charges ranging from a violation of probation to the aggravated unlicensed operation of a motor vehicle. Just when he seemed like his legal troubles were over, he was arrested again in 2021 for trying to profit off of recovering patients.

Rapper Tyga was extremely candid with his fans when he revealed that he never met his father Stevie Stevenson. The musician’s father is currently serving life in California’s Solano State Prison. Shortly after Tyga was born in 1989, Stevenson stepped out of his son’s life before being imprisoned in 1991 due to kidnapping charges and more. He wasn’t initially aware of what all of his children were doing while he was behind bars. Stevenson even had to learn that his son Tyga had become famous second hand. At the same time, the rapper has spoken about his absent father on numerous occasions. The morose track “Dad’s Letter” is a particularly poignant example of Tyga speaking up about his relationship with his father.

This country music star and “American Idol” alum had a rocky upbringing in North Carolina. Since both of her parents were M.I.A. at different times in her childhood, she lived with her grandparents for a large portion of her early years. Although Pickler went on to become a household name due to “American Idol”, her father Clyde Pickler Jr. kept getting in legal trouble. Throughout his life, he was convicted of crimes such as stabbing a neighbor and stealing vehicles. Pickler Jr. actively kept in contact with his daughter and tried to repair their relationship when he was released. They seemed to be in touch until his death in 2019.

Although Drew Barrymore’s dad had big Hollywood aspirations, his career was derailed by a number of arrests. In December 1958, John Barrymore was sent to jail for engaging in a drunken fight with his then-wife, Cara Williams. Just three months later, he allegedly engaged in a hit and run and was arrested yet again. The ‘60s were a particularly turbulent time for Barrymore. He found himself in and out of prison for various charges that ranged from possession to public intoxication. All of these incidents made it hard for his daughter to have a connection to him. However, Drew Barrymore did what she could to help her father with health issues until he passed away.

Drake’s father Dennis Graham was once an accomplished musician. At one point, he even worked with Jerry Lee Lewis as a drummer. But early on in Drake’s life, Graham’s legal problems in the states kept him from visiting his son in Toronto on a regular basis. This fraught relationship has been brought up in several Drake songs. And things didn’t improve much when Graham was arrested for drug charges. While he has argued that he was more present than it may appear, it’s clear that the musician didn’t feel the same way. In an interview with Complex magazine in 2011, Drake even said that he “didn’t have a father.”

This Oscar-nominated actor had a horrible experience with his dad early in his life. His father Tyrone Howard tormented and mistreated him on multiple occasions. And in 1971, a terrible incident would forever change their family dynamic. When Tyrone Howard took his family to take pictures with Santa at a mall, they were accused of cutting in line. This accusation led to the patriarch having a physical altercation with a man named John Fitzpatrick. During the fight, Tyrone Howard fatally stabbed Fitzpatrick in an incident that would be known as the Santa Line Slaying. He eventually served 11 months in prison for the crime. Following this grim incident, Terence Howard’s parents separated.

Before Keanu Reeves had started school, his father had walked out on the family. The father and son would only meet periodically after that point. Sometime between their sparse meetings, Samuel Reeves Jr. struggled with addictive behaviors and breaking the law. In 1992, the same year that “Bram Stoker's Dracula” premiered, Reeves Jr. was arrested for selling heroin at Hawaii’s Hilo Airport. He spent two years of a ten year sentence behind bars. In recent interviews, Keanu Reeves has confirmed that his relationship with his dad has remained extremely strained. For his part, Reeves. Jr. was quoted as saying his son “wants nothing to do with [him].”

When Lee-lee Chan was struggling with hard financial times and the recent loss of her husband, she abandoned her daughters in a Shanghai train station around 1945. She then began to try to make money selling opium at the Shanghai ports. However, her life changed when she was nearly arrested by her future husband and inspecting officer Charles Chan. Before he could take her in, he recognized flowers in her hair that symbolized that she had lost family members. This sight encouraged Charles Chan to let her go without pressing charges. Thanks to this show of kindness, the two were able to build a strong relationship and went on to have Jackie Chan.

The “Gossip Girl” and “Single Parents” star had to overcome a tremendous amount to become the famous celeb she is today. Before she was born, her parents Douglas Jay and Cosntance Lynn both participated in an illegal international marijuana operation. At the time they were sent to prison, they also knew that they were going to have a baby. Constance Lynn Meeseter was allowed to give birth outside of prison. While she finished her sentence, Leighton Meester was taken care of by her grandparents. Many years after the turbulent circumstances of her birth, the actress has expressed that she “doesn't judge them” for their past choices.

The first assassination of a federal judge in the 1900s was actually carried out by Charles Harrelson. He was a professional hitman who was allegedly responsible for taking numerous lives over the years. At one point, he also participated in an armed robbery. In 1973, Charles was sentenced to fifteen years for slaying Alan Berg and served only five. It was after this sentence that he was convicted of his most infamous crime. In the late ‘70s, Harrelson was slapped with two life sentences for assassinating a District Judge named John Wood Jr. He was reportedly hired by another criminal named Jamiel Chagra who was trying to avoid a harsh conviction. Harrelson died in a supermax prison called ADX Florence in 2007.