Top 10: Dysfunctional Families

#10 - The Gosselins

Children used for fame and financial gain are a common theme on this list. When a family, like the Gosselins of Jon & Kate Plus Eight fame, become financially dependent on their children’s earnings and the line between parent and manager becomes blurred, dysfunction always follows. In this case, the children seem reasonably well-adjusted, but the parents are a mess. Jon Gosselin is a man-child desperately trying to recapture his lost 20s. Kate Gosselin is a spurned woman who drapes herself in the flag of single-motherhood, while desperately trying to stay in the spotlight of television.
Avoid their fate: Fertility treatments and reality television are risky ventures -- avoid both at all costs. 

#9 - The Keatons

Issues: Alcohol, pathological mooching
The dysfunction in Buster Keaton's family plagued the silent-screen star for his entire life. As a toddler, Buster joined the family's vaudeville act and quickly became the family's breadwinner, a role he would retain for his entire life. Neither of Buster’s parents, nor his two younger siblings ever made serious attempts to earn money of their own.
Buster’s divorce from Natalie Talmadge was one of the messiest Hollywood has ever seen. By the end, Natalie managed to take 90% of the couple's shared assets, including Buster's mansion, yacht and dog, the last of which she sold without consulting Buster. She also changed their children's name from Keaton to Talmadge.
Avoid their fate: The first lesson is not to let your family get too comfortable. Lifestyles are to be worked for, not bought by your more successful family members.

#8 - The Windsors

Issues: Divorce, death, costumes in poor taste
Dysfunction in the royal family goes back too many generations to cover in this list, so let’s focus on Prince Charles. He marries Diana Spencer in 1981, in what was believed to be a fairytale wedding, but by the late ‘80s the marriage was falling apart. Charles was having an affair with Camilla Parker-Bowles, while Diana too was stepping outside of the marriage. Her extramarital relationships were tabloid fodder for years following the couple’s separation in 1992. These are all pretty normal dysfunction, but when it happens to a royal, it makes for better copy. So does an ill-conceived Nazi costume worn to a theme party -- too soon, Prince Harry. 
Avoid their fate: Don’t marry someone just because you have the approval of Her Majesty's Most Honourable Privy Council.

#7 - The Barrymores

Issues: Estrangement, drugs, alcohol
Born into an acting dynasty, Drew Barrymore was a star at 6 years old. Her grandfather, John Barrymore, was one of the greatest actors of his generation, but was also a raging alcoholic. Her father, John Barrymore Jr. was a self-destructive failure. Drew’s mother, Jaid, was known for using her famous daughter as a prop and her key to the high life. She would drag the young Barrymore to parties and to Studio 54, where Drew began using drugs. By the age of 13, Drew would enter rehab for alcohol and drug abuse. At 15 years old she would be legally emancipated from her parents, after which she was able to rebuild her life and a successful career.
Avoid their fate: Again, famous kids should not be managed by irresponsible adults.

#6 - The Baldwins

Issues: Hot tempers, divorce, financial troubles
Remember in the early 1990s when being called a “Baldwin” meant you were a hot guy? Now, it’s more likely to mean you’re an overweight hothead or drug addict. The Baldwin brothers have had their fair share of problems in recent years. Daniel has battled his weight and drug problems on reality TV. Stephen has spent a decade starring in Celebrity Apprentice and I’m a Celebrity…Get me Out of Here! Alec Baldwin has had a career high with 30 Rock, though his personal problems since divorcing Kim Basinger have made front page news. Most notable was the nasty voice mail he left his daughter in which he calls her a “rude, thoughtless little pig.” Only Billy Baldwin has managed to live a relatively normal life, despite being married into the Philips family.
Avoid their fate: Above all else, never leave an angry voice mail.

#5 - The O'Neals

Issues: Drugs, violence
It’s not a good sign when matching father and son mugshots turn up in the results of a quick Google Image search for “Ryan O’Neal.” He may be an Oscar nominee, but Ryan certainly would never win a "Father of the Year" award judging by how his kids have turned out. Tatum stands as the youngest ever Oscar-winner, but has continually struggled with drug addiction. In 2008, she was busted for trying to buy crack. Griffin, Tatum’s younger brother, was involved in an incident with his father that resulted in his pregnant wife getting hit with a fire poker, and Ryan being arrested for firing a gun. O’Neal’s youngest son, Redmond, has also had several drug-related run-ins with the law. In 2009, he had to be given a day pass to attend Farrah Fawcett’s (his mother) funeral.
Avoid their fate: Remember that it’s not the ‘70s anymore and you can’t go around on crazy drug binges while firing off guns.

#4 - The Lohans

Issues: Fame-whoring, domestic abuse
It was just a few years ago that Lindsay Lohan was drawing comparisons to the likes of Ann-Margret. DUIs, rehab stints and an open letter from a producer calling her “unprofessional,” and Lohan’s derailed her career before it got a chance to pick up speed. Her parents are no better. Her father, Michael, has served jail time for stock fraud and probation violation, including a DUI of his own. Her mother is desperately trying to cling to fame through her children, pushing her lifeless daughter Ali into the limelight on the reality series Living Lohan.
Avoid their fate: Lindsay should have taken a page out of Drew Barrymore’s book and sought emancipation from her parents.

#3 - The Burroughs/Finches

Issues: Mental health problems, underage sex
If we’re to believe all of the dysfunction that is outlined in Augusten Burroughs’ memoir Running with Scissors, he grew up with a mentally disturbed mother, who dated a teenage girl and saw her psychiatrist once a day. When Burroughs' parents divorced, his mother sent the boy to live with her psychiatrist, Dr. Finch. Finch doesn’t believe in rules for adolescents. He allows the 13-year-old Burroughs to smoke pot, have sex and begin a relationship with a 33-year-old man. Burroughs’ adolescence was plagued with sexual misconduct bordering on assault, and psychotic episodes from his mother.
Avoid their fate: Kids need rules.

#2 - The Phillips

Issues: Drugs, molestation, incest
“Papa” John Phillips of The Mamas & The Papas had some serious issues. In her autobiography High on Arrival, John’s eldest daughter Mackenzie revealed some shocking things about her relationship with her father. First, that he got her hooked on drugs, going as far as injecting her with cocaine. She also alleged that the two had a consensual sexual relationship that lasted several years. That’s dysfunction.
Avoid their fate: A good start would be to not to have any sort of physical relationship with anyone in your bloodline. Period.

#1 - The Jacksons

Issues: Child abuse, plastic surgery, general nuttiness
The Jacksons are America’s first family of dysfunction. The saddest part about the Jacksons -- aside from the persistent accusations of child molestation against Michael, the estrangement and tell-all books by La Toya, Joe’s belief that his children’s success justifies the abuse he doled out -- is their collective delusion that they’re a family dynasty that remains relevant in American culture.
Avoid their fate: Don’t try and make a living off of your kids’ talents, especially when only half your children have any talent to speak of.