Woody Harrelson.  His dad was a contract killer, who went to prison for his crimes.  He was released on parole, but then he was hired to kill a judge... and was sent back to prison until his death.

Kelsey Grammer.  When he was a kid, his dad was shot to death by a cab driver on his front lawn.  When he was 20, his sister was brutally murdered by a gang of thieves that were robbing a Red Lobster she worked at. On top of that, his two half-brothers died in a scuba diving incident, where one of them was EATEN BY SHARKS.  And then, later in life, a close friend of his died in the 9/11 attacks.

Dylan McDermott.  After his parents divorced, his mom dated someone who reportedly had ties to organized crime.  She was later found dead.  Police believe the man killed her... but HE was later found dead in a parking lot. Of course, later in her life her boyfriend Patrick McDermott mysteriously disappeared following a fishing trip in 2005.  He was never found, although some people believe he faked his death and is hiding out in Mexico.

Jackie Chan.  After the death of her first husband, his mom became a gambler and opium smuggler.  However, Jackie didn't know this until later in life, because his parents had abandoned him when he was young.  He was left in the care of someone else... but he and his parents later reconciled.

Charlize Theron.  Her father was an abusive alcoholic.  During one altercation when she was 15, her father attacked her and her mom and threatened to kill them.  In self-defense, Charlize's mom shot and killed her dad in front of her.

Kevin Spacey.  His older brother has said he was abused by their father... and that their dad was also part of the American Nazi Party, who would supposedly even make himself up to look like Hitler.  Their dad sent Kevin to military school, but he hasn't commented on his father's alleged past.

Rose McGowan.  When she was a kid, her family was involved in a cult.  They left when her father decided that the cult's teaching of sexual relationships between adults and children was inappropriate.  Ya think

Demi Moore.  Her mother was a teenager when she was born, as well as an alcoholic with bipolar disorder.  Her stepfather was also an addict, who struggled to keep a job, resulting in them moving more than 15 times.  They were both very abusive parents.  Her stepfather eventually committed suicide.

Facts courtesy of Wikipedia.