The apple doesn’t fall far from the tree, or in Lindsay and Michael’s case, the gavel doesn’t fall far from the Lohan. American actress, Lindsay Lohan was just launching her young career when her Wall Street trader father was first jailed for criminal contempt of court while being investigated for insider trading. Michael spent three years in the slammer, with five years probation after release. He violated his probation when he flew to Napa, California to visit Lindsay and was sentenced to another year in jail. One would think that four years behind bars would straighten Michael out, but his intimacy with law enforcement was just getting started. His later legal woes included two attempted assault charges, a DUI charge, failure to pay, and domestic violence. He was obviously a very bad role model for Lindsay who now has a legal record that rivals her fathers.
2. Woody Harrelson
American actor Woody Harrelson’s father, Charles, leads a colorful life that reads likes a movie script. Charles, a down on his luck encyclopedia salesman with a gambling problem, morphed into a freelance hitman with increasingly prominent victims. Charles’s first “job” was Alan Harry Berg. Berg was a carpet salesman for his family’s business and was the unfortunate rival of another low-end carpet business’s salesman. The competitor hired novice hitman, Charles for $2,500 and, shortly after, Berg went missing. Charles was tried and acquitted for the killing. That same year Charles was tried for the murder-for-hire killing of Sam Degelia, Jr, a Texas grain dealer who was killed for a life insurance payout. The jury was deadlocked, and Charles once again got away with murder; however, only until 1973, when he was retried and sentenced to 15 years in prison. Often described as charming, Charles only served 5 years before being released for good behavior. He was far from reformed and arrested in 1979 for the killing of Federal Judge John H. Wood Jr. Wood was shot in the back the same day he was going to sentence drug trafficker Jamiel Chagra. The connection was not initially made, but Chagra had hired Harrelson to take out Wood. Wood had a reputation for handing down long prison sentences for drug offenses—he was nicknamed “Maximum John”. Thanks to a recorded conversation about the killing between Jamiel and his brother, the FBI had enough evidence to put Charles behind bars for two life sentences. Charles died in prison in 2007.
3. Leighton Meester
Gossip Girl star, Leighton Meester, was in utero when her mother Constance was convicted and sentenced to ten years in prison for her involvement in a drug smuggling ring. Constance and Leighton’s father, Doug, smuggled 1,200 pounds of marijuana from Jamaica to the United States. Constance gave birth to Leighton in a hospital and was allowed to nurse her in a halfway house for three months before giving Leighton to her grandparents to raise.
4. Kellie Pickler
With an upbringing like Kellie Pickler’s, it’s no surprise that she became a country singer. Between her southern upbringing (North Carolina) and alcoholic and often incarcerated parents, she has enough to croon about for decades. Kellie’s mother, Cynthia Morton, had a habit of writing bad checks and once tried to pass a forged prescription for Valium while she was working at Walmart. Kellie’s father’s criminal record rounds out the couple’s range of offenses nicely with prison sentences for armed robbery, aggravated assault, and battery—a charge which came after he stabbed his neighbor in a trailer park.
5. Jackie Chan
Actor Jackie Chan’s parents had a wild and harsh life, but they managed to make it through without breaking too many laws. His father, Charles Chan, lived through the Chinese Civil War. He was a Secret Agent for the Nationalists and took a bullet on two separate occasions, purportedly from Communist assassins. Chan’s mother, Lee-Lee was widowed and broke when the profitable profession of opium dealing lured her. She bought opium, but was caught at port inspections by Charles Chan. Chan took pity on his future wife and let her go without any trouble. Lee-Lee began gambling and was quite good at it. During this time, she and Charles became close and married, eventually giving birth to one of today’s greatest action movie stars, Jackie Chan.