20 Epically Dysfunctional Rich Families

Dysfunctional families make for epic entertainment. The Simpsons, Little Miss Sunshine and Modern Family, to name a few, have demonstrated this idea well.

But in all fiction lies a grain of truth–real-life dysfunctional families prove that fact all the time. And the more money the family has, the worse it seems to get. The families below offer some impressively painful examples:

20. The Favres

Meth, manslaughter and machismo–what do all of these things have in common? Why, the Favre family, of course.

Arguably the most famous member of the Favre family is Brett himself. Whether or not you like football, this guy is pretty impressive, on the field at least. His career spanned 20 years and four teams–the Atlanta Falcons, Green Bay Packers, New York Jets and the Minnesota Vikings.

But his personal and family life are much more sordid. Favre’s 1996 Vicodin addiction was the first, but not the worst, piece of the football player’s misconduct. Favre also seems to think he’s God’s gift to women who like tall strapping lads. He got slapped with three separate sexual harassment suits, one from a former New York Jets sideline reporter–she received pictures of Favre’s man parts on her cell phone–and two others from team massage therapists.

Not willing to let her brother hog all the limelight, sister Brandi, who has previous weapon-related charges, was arrested at a meth lab this January. And let’s not forget big brother Scott. He actually killed a buddy while driving drunk. He has also been quoted as saying that he’s “retiring” from people “knowing who the f*ck he is” based on his little brother’s celebrity. Right.

19. The Sheens

Sheen family patriarch Martin seems to have his head on pretty straight. His son, Emilio, whom you might remember from such Hollywood ’80s staples as The Breakfast Club, seems like a levelheaded guy as well.

This begs the question: What in God’s name happened to Charlie? While the other members of the Sheen/Estevez clan handle the strain of their celebrity with a minimum of damage, Charlie almost seems to relish getting into trouble. The Two and a Half Men is firmly implanted in the ranks of celebs who treat rehab and/or jail like it has a revolving door.

It’s ironic that his character in Two and a Half Men was loosely based on Sheen’s image as a media whore with substance abuse problems, because now, Two and a Half Men is on hiatus while he goes back into rehab–after trashing a hotel and scaring his escort bad enough that she hid in the closet until the fuzz arrived.

Sheen now augments his rehab efforts by living with two porn stars. He says his situation is “just filled with just wins” and that he’s “honored to be mentioned in the same sentence” as Hugh Hefner. Oddly enough, he never mentioned acting. We’ll see how long it takes him to get back on the ball (or off his balls) this time.

18. The Agassis

“Tennis is your life. You will eat, sleep and crap tennis. Tennis will be your best friend and your most amorous lover. And if you do not play, well, that is not a consideration. You will play, and you will be good, dammit. The very best!” Andre Agassi’s drill-sargeant father isn’t recorded as saying this all a la Full Metal Jacket’s R. Lee Ermey, but he might as well have.

Day in and day out, the elder Agassi ran his son mercilessly through his own brand of tennis boot camp. Who knew that watching two adults sprint around, batting a tiny ball over a net was so insane?

Daddy’s constant tennis hard-lining did have the the expected result, in that it turned Andre into a kind of tennis-playing superhero. He even cultivated a deep, dark hatred of the sport, similar to the rage that drives the Dark Knight. But Batman never snorted meth when the rigors of bringing the Joker back to Arhkam Asylum (and having him escape…again) got him down.

17. The Barrymores

Image: David Shankbone
Young stars should never be managed by their immediate family. The Barrymores will be happy to provide a stark example of just why this is a stupid idea.

Bear in mind that the Barrymores predating Drew weren’t exactly talentless hacks. John Barrymore, Drew’s grandfather, was one of the most famous and much sought-after actors of stage and (early) screen in his day. Unfortunately, he was also a raging drunk.

And then we come to the generation that spawned the adorable little blonde girl, Gertie from E.T. It wasn’t her debut, but it was most certainly her breakout role. John’s son, Barrymore Jr., was also an actor, but never held a candle to his sire’s success.

What did Mama Barrymore do? She knew her hubby was a wash, so she used her daughter like a meal ticket. Parties, hobnobbing with the elite of the elite, probably some drugs too.

Drew got into drugs, probably as a coping mechanism, and because all the rich kids were doing it. But after she turned 15, she got herself legally emancipated from the coattail-riding Barrymore matriarch. The rest, as they say, is history.

16. The Hearsts

Newspaper mogul William Randolph Hearst, along with archrival Joseph Pulitzer, helped define journalism as we know it today—despite the fact (or maybe because) their style involved sensationalist “yellow journalism.”

Hearst padded his success by buying lots of really expensive and sometimes weird properties, including Hearst Castle and the Beverly House. He married the daughter of a brothel owner, Millicent Willson, then cheated on her openly with actress Marion Davies, with whom he illegitimately bore actress Patricia Lake. Other Hearst pastimes including verbally trashing Adolph Hitler and being blamed for the Spanish-American war.

With a history like that, no offspring can escape controversy for long. In Hearst’s case, it was granddaughter Patty who hit the notoriety jackpot. She was kidnapped in the ’70s by a guerrilla terrorist group called the Symbionese Liberation Army (SLA). Their demand in ransom was that Patty’s father donate what amounted to $400 million in food to the poor folks of California, where the Hearsts were living.

Unlike some wealthy sorts (see the Gettys), her father made a fair effort, though he “could have done better,” according to his daughter. She was with the SLA long enough to develop Stockholm Syndrome. She robbed a bank and got thrown in jail. She was supposed to serve 35 years, but her sentence was commuted twice–once to seven years, and the second time by President Carter to only to time served. Later still, President Clinton issued her a pardon.

Now, how’s that for a sensational story?

15. The Osbournes

You probably wouldn’t expect that, of all the entries on this list, Ozzy Osbourne’s family would be one of the most well-adjusted, would you? The Osbournes proved, during their reality show’s run from 2002-2005, that the Prince of Darkness and his family are amazingly normal.

That’s not to say that the show wasn’t without its strife and shenanigans, however. At the core of the Osbourne family philosophy (which Ozzy himself lamented the lack of many times during the course of the show) is a simple idea: to be left the hell alone. This is why The Osbournes didn’t have the same mansion-cum-fishbowl feel as many other reality shows.

Sure, Sharon’s ever-increasing mob of pint-sized quadruped friends tended to get underfoot and roam all throughout the house, like an inopportune, surprise-leaving tide of canine superiority, but this wasn’t even the best part of the show. Something else this show had in contrast with its contemporaries was that one of the cast was the producer as well. Sharon had final say about what was in or out.

Jack and Kelly led fairly normal lives, even if Jack spilled the beans on the ‘unscripted’ nature of the show, much to his mum’s chagrin. Kelly threw a wobbly (got angry, British slang) at her brother more often than not, but when do siblings not fight? And at the head of the table, you had Ozzy, as befuddled as ever, with a surprising dose of ‘teddybear’.

Aww. Kinda tarnishes the whole Iron Man image, doesn’t it?

14. The Windsors

There’s not a royal bloodline in the books without an equally blue-blooded strain of dysfunction. The Windsors’ most famous example to date involves Charles the fairytale Prince to Diana’s Cinderella in 1981.

For a few years, all was bliss, or so we were all led to believe. Then Charles decided to honor his wife and the bonds of matrimony by shacking up with mistress Camilla, who he later married. Princess Di returned the favor and landed a lover of her own. Their divorce rivaled Edward III’s abdication in 1936 for sheer spectacle–and went forward for probably the same reasons as Edward’s passing the throne to George VI.

The annals of family debauchery go back much further than Charles and Diana, with Windsors marrying their first cousins and doing God knows what else behind closed doors. If Prince William and Kate Middleton hold true to the royal legacy, expect to see even more dysfunction.

13. The Bushes

La familia Bush arguably rivals the Kennedys in terms of scandals and pure dynastic insanity. One of the biggest Bush faux pas in recent memory is the Savings and Loan scandal of the 1980s and 1990s. Here, Neil, George (Senior and Junior) and Jeb, along with a whole slew of politicians–many of whom are still in office–were implicated in various financial debacles that ended up costing taxpayers $153 billion bucks.

Neil was the main focus of the investigation, which concentrated on questionable and outright illegal business practices designed to enrich the Bush clan and their cronies. Luckily for Neil, Papa Bush saved his sorry backside from the Big House. By this time, Bush Sr. had been elected to the White House, and had announced the beginning of Desert Storm.

Jumping ahead a few years, we have George Jr. in the hot seat. Even if we spare an analysis of the man himself, George Jr’s daughters have shown a delightful knack for keeping the Bush family’s impeccable sense of propriety alive and well.

Case in point: While it may not be unusual for underage people to drink (they’ve been doing it for years), when Jenna was 19, she got busted for underage drinking in her daddy’s home state. So, get this, the Secret Service cozied up to their Mexican counterparts so that Jenna could flee the fuzz in Texas and go barhopping south of the border. Now if that’s not international cooperation, we don’t know what is.

12. The Crawfords

What is it about success that turns people into overbearing, abusive drunks? Career fixation is one gateway neurosis, especially a meteoric rise like the one that Joan enjoyed in the early and mid 20th century.

In her 1978 book, Mommie Dearest, her adopted daughter Christina laid the Crawford home bare. In it, she alleged that both Joan and her brother abused her physically and emotionally. That got Christina kicked out of her mom’s will, something she claimed in the book that she wouldn’t let happen.

Meanwhile, the other two Crawford kids and a host of Joan’s Hollywood friends, including Marlene Deitrich and Cesar Romero, denied the allegations. In the end, however you slice it, Joan was career driven. Whether or not you believe she had her kids as a publicity stunt to further her career, her booze-fueled tantrums could make Christian Bale’s Terminator Salvation shenanigans look like a kiddie play.

11. The Gettys

If family loyalty means anything to you, you probably aren’t a member of the Getty clan. The original Jean Paul Getty was an exceedingly wealthy industrialist in the States. When he died in 1976, worth more than $2 billion, he was ranked the 67th richest American who ever lived.

Indeed, in the Gettys’ case, ink is thicker than blood. Back in 1973, Jean Paul’s 16-year old grandson, Jeann Paul Getty III, was kidnapped while vacationing in Rome. A ransom of $17 million was ordered over the phone.

The miserly Getty refused to pay it. He claimed that his grandson was merely trying to mooch off of him. He said that if his grandson had been kidnapped, and the senior Getty gave in to the kidnappers’ demands, it would be putting his 14 other grandkids at risk. (We assume his 14 other grandkids were fine, moral, upstanding kids who wouldn’t dream of ripping dear old Granddad off.)

The kidnappers lopped off one of the boy’s ears and sent a letter along with the ear, demanding a reduced $3.2 million. In the letter, they threatened to send Jean Paul III back to his family in little bits and pieces if Gramps didn’t pay up.

The senior Getty still had a hard time protecting his own flesh and blood over his own interest (accumulation, that is). Eventually, he agreed to pay the kidnappers $2.2 million, the smallest tax deductible amount allowed by law.

The traumatized Getty III couldn’t cope with his dismembering adventure in the Eternal City. After he came home, he doped himself to the gills with drugs. After overdosing on Valium, methadone and alcohol, he suffered a massive stroke that left him paralyzed; he lived like this for another 30 years.

10. The Gottis

John Gotti, the media-loving “Teflon Don” of New York’s notorious Gambino crime family, had quite the family history before being thrown in the slammer in 1992. The truant son of a gambler held one legitimate job during his entire career, but that didn’t last long. Brothers Gene, Richard and Peter were also part of John’s crime family. John was reportedly jealous of Gene for being “made” (murdering someone to join the Mafia) before he was, and for being a better gambler than him. Brother Richard was convicted of statutory rape and for trying to extort money from Steven Seagal.

With that kind of foundation, how could the brothers’ many kids not be messed up? Gotti’s son, John Gotti Junior wasn’t much of a man in his father’s eyes. The heir to the Gambino throne, Junior was kind of inept. Apparently, everyone in his family hated him and thought he was an “imbecile,” a “babbling idiot,” and worse. He’s not doing too bad now, though—he’s in talks to make a movie and has penned a children’s book named “Children of the Shaolin Forest.”

John’s daughter Victoria arguably fared better, starring in the reality TV series Growing Up Gotti. She also faked breast cancer and had her home foreclosed on. Cousin Richard G. Gotti racketeered money from a pre-school he and his wife ran. The stories go on, as you’ll see in a couple of years when the biographical movie on Junior comes out. (Note that it may feature fellow dysfunctionista Kim Kardashian.)

9. The Jacksons

The world of the Jackson family, one of the most famous families in the history of modern music, is one of debauchery, animosity and betrayal.

When he was alive, Michael reportedly hated his family, except for his mother Katherine and youngest sister, Janet. LaToya, in her autobiography, wrote about physical abuse, jealousy, and racism. When the book came out, Janet called it “a load of crap,” and younger sister Rebbie said it made her “ashamed to be a Jackson.” Michael, meanwhile, said the physical abuse part was true on Oprah.

Maybe the rest of his family could explain why Michael’s private life was such a twisted fairy tale, one that no sane kid would ever want to be a part of. We aren’t just talking about the numerous kids who visited on day trips but also about his three children, Prince Michael I, Paris Michael Kathrine and Prince “Blanket” Jackson II. On the surface, Michael’s former home, Neverland Ranch, is a child’s fantasy. Amusements, rides, a “petting zoo” in the basement, just to name a few. But what about the garage full of windowless vans? That just screams pedo with an ice cream truck and a kidnapping fetish.

The moral of the story: Musical talent does not a happy family make.

8. The Hiltons

It seems that an obnoxious propensity for getting your face plastered all over the news, the cover of tabloids, and even on YouTube (yes, we are looking at you, Paris) goes hand-in-hand with wealth and privilege. If you lack talents outside of socializing and being seen, you become a so-called “celebutante” like Paris.

Paris seems to reaffirm her questionable ethics and business acumen every time she opens her mouth or tries a new, soon-to-fail venture. Cases in point: Her Chihuahua Tinkerbell, uh, wrote a book called “The Tinkerbell Hilton Diaries.” She turned her homemade sex tape into a DVD (okay, maybe that wasn’t so dumb). A bunch of her personal belongings, including diaries and medication, made it online after she refused to pay the $200 or so fee for the storage locker they were stored in. After getting a DUI, she drove like a madwoman on a suspended license, and was finally thrown in the slammer for it. She’s been caught traveling with pot and cocaine.

But when her mom joins in the fun, like some creepy elder groupie, it just looks plain wrong. And the family tangent doesn’t stop there. Uncle Nicky Hilton slept with Zsa Zsa Gabor—while his dad, chain founder Conrad, was married to her. Another son, Barron, felt he wasn’t left enough money after Conrad died; he contested his paltry $500,000 inheritance and won more. In a twist of irony, Barron himself plans to leave most of his fortune to his father’s charity, because he is reportedly embarrassed by Paris’ behavior. Karma is a b*tch indeed.

7. The Hogans

Hulkamania’s running wild, but for all the wrong reasons. Hogan and his wife split up after the end of their reality show, Hogan Knows Best, and he shacked up with some other woman (in his defense, their age difference isn’t quite as telling–only 22 years. He’s 57). However, his now ex-wife, who is 51, shacked up with a 21-year old.

Furthering the drama–though in a distinctly age-appropriate fashion–Hogan’s son Nick has a need for speed, kind of like Goose and Maverick from Top Gun. Like Goose, Nick’s friend died horribly when Nick did something stupid. And now he must live with the guilt every day, just like Maverick.

Last but not least is Brooke, Hogan’s daughter/Nick’s sister. She’s doing what she can, but rather than shack up with a guy old enough to be her father, she started a crummy music career and, in a blaze of originality, a reality show of her own to raise funds for her musical talent called Brooke Knows Best. Maybe American Idol is to blame, along with YouTube, since so many people think they have the stones and the talent to get by. But a family history of reality flops and PR stunts certainly helps, too.

6. The Kardashians

The pedigree for crazy shenanigans and questionable life choices is strong in this family. To start, Robert Kardashian was once part of O.J. Simpson’s team of top tier lawyers. You all know how well that worked out. Together, he and wife Kris had three daughters, whose name all begin with K.

After Robert’s death, Kris married former Olympian Bruce Jenner (why she didn’t pick somebody like Kevin Kline is beyond us). But what started the Kardashians’ true rise to “super stardom” as the front-runners of a mediocre, brain-rottingly bad reality show?

Before Keeping Up With the Kardashians, virtually nobody knew who the heck they were.Then daughter Kim went and did the nasty with former R&B singer boyfriend Ray J, all caught on tape. Silly her for not keeping that tape locked up tighter than a nun’s virtue.

What of the rest? Khloe is an unrepentant drunk with no sense of decency (do you ask your mom if she performs oral sex on her husband? We didn’t think so). Considering that the show entered its third season not long ago, we can’t help but compare this messed up clan, in their hunger to expand and conquer all aspects of good taste and decency, with the Cardassians, a race from Star Trek. They have a similar all-consuming desire to mess your sh*t up and look smug and self important while doing it.

5. The Spellings

Everything from Gun Smoke to Beverly Hills 90210 had 1980s and ’90s-era TV and film producer Aaron Spelling’s hand in it. As such, he was fabulously wealthy.

Yet life at home wasn’t all cupcakes. Daughter Tori refused to talk to her mom (Aaron’s wife) Candy for years. Oddly, both mother and daughter released their memoirs–Stories From Candyland and sTORI Telling, respectively–when they weren’t speaking.

When Tori’s dad died in ’06, she never showed up for the funeral, then made some creepy appearance on the cover of US Weekly. Did she mention her father and his passing? No, that’s what makes it so weird. She claimed her mom was “with some male friend.” Did her estrangement damage her perception that much? Yeesh, it sure sounds like it.

4. The Kennedys

Ah, the Kennedys. This dynasty known for its many members who gave tirelessly of themselves in diverse and long-lasting (in most cases) political careers. They are also known for the many and varied scandals that lurked just below the surface, sometimes bursting into the light like a geyser of depravity.

A majority of the gents in the Kennedy clan were prone to sowing their wild oats with as many women as was humanly possible, not unlike a porn star, but cleaner, we hope. But political hanky panky wasn’t the only thing the Kennedys tried to keep hidden away to preserve the family’s perceived sterling image.

Take, for example, “Rosemary” Kennedy, born in 1918. Sibling to the future Commander-in-Chief, she was different. In a family known for its competitiveness in all things, Rosemary’s mood swings and rebellion were seen as unpalatable. When she was 23, Daddy Joe secretly had her lobotomized, tamping out the spark of whatever might have been. A now-familiar series of plane crashes, car wrecks, assassinations (and rape, stillborns, cocaine, and ski accidents) followed.

Genetic recklessness? Family curse? The mystery remains. Maybe Jack’s famous line should have been, “Ask not what your country can do for you, but what the leader of the country can do to you.”

3. The Lohans

Love her or hate her, Lindsay Lohan has a knack for legal troubles and ruining her reputation with every stunt she pulls. But maybe we should go to the root of the problem–her parents.

Mom (Dina) and Dad (Michael) made a habit of yo-yoing back and forth between being together and breaking up so many times, it’s a wonder that Lohan and her younger sibs didn’t all run away to join the circus. They finally divorced for good (we think?) in 2007, but who knows how long that will last.

The parents of celebrities have never been, so far as we know, stable, rational or equitable people. They often pull the same stupid stunts as their kids. Take Michael, for instance. A former trader on Wall Street, and owner of his father’s pasta company, the senior Lohan served jail time for stock fraud and a DUI, among other things.

And Lindsay’s mom? She was a media whore, riding on the coattails of her eldest daughter in order to get a taste of the life afforded by Lindsay’s numerous movies (starting with The Parent Trap in 1998).

Lindsay really could have been something special, but instead, she had to go and ruin the ride. If she had at least gotten herself emancipated, she might have done better. With Lindsay’s legal troubles putting her career in jeopardy, Dina has turned her fickle attentions to Ali Lohan, Lindsay’s younger sister, in the hopes of making the girl a singer and just as famous (or infamous?) as Lindsay herself.

Problem is, Ali has neither the inclination nor the chops to do what her sister has done. It all goes back to the parents. Of course Dina thinks that riding her daughter into the ground in a saddle of celebrity is a good idea. But what do the Lohans know about those?

2. The Spears

Let’s play make believe. You are the mother of three children. You pride yourself in the wholesome, proper way that you bring up those kids.

One of those kids makes it big at a pretty young age, during the late ’90s. She becomes a teen pop sensation almost overnight. Yet as her fame increases, her life of excess and her mismanaged career take their toll. Note that you, dear mother, were on tour at one point to help manage her career.

Then, your other daughter, who is unwed, goes and gets pregnant. Imagine that, taking irresponsible cues from her superstar sib! Do you, the mother, even have a leg to stand on when it comes to the topic of good parenting? Yet you still have the brass to put out a book about how you’re mother of the freaking year.

I you can take any consolation, Britney has followed in your footsteps. You saw how she treated, then lost her kids from K-Fed, right? And let us not forget the wildly immature string of marriages preceding her shacking up with Federline (who, in one of the most contentious “lesser of two evils” custody cases, ended up with their child after she went back into rehab).

Oops. She did it again. And will probably keep on doing it.

1. The Simpsons

OJ Simpson is arguably one of the most prominent former football players of his generation. Yet most of OJ’s celebrity comes from the media circus created by his high-speed chase down the 405 in LA after the murder of former wife Nicole and her friend Ronald in 1994.

The second act of the fiasco began about sixteen months later, with the trial. Yes, the trial that saw OJ acquitted because the “glove does not fit.”

But that mess, one of the biggest debacles in the history of law, was not the end of the legal shenanigans. OJ fled to Miami, where he was eventually busted for assault and burglary. On a separate occasion, the fuzz caught him speeding in his boat through what amounted to a ‘manatee crossing’. He was acquitted of those charges too.

But the slippery OJ would soon get caught once again. In 2007, he and three other men broke into a Las Vegas casino to steal sports memorabilia that OJ claimed had been stolen from him. A kidnapping was also involved.

Naturally, his two associates testified against him, and now the Juice is no longer loose. He’ll be locked up at least until 2019 when he gets his parole hearing, but more than likely, he’ll stay down until 2045.

Written by Drea Knufken

Currently, I create and execute content- and PR strategies for clients, including thought leadership and messaging. I also ghostwrite and produce press releases, white papers, case studies and other collateral.