A Look Back at the Heart-Breaking Life of Anna Nicole Smith and Where It All Went Wrong

Tue Sep 14 2021

Before there was Kim Kardashian, there was Anna Nicole Smith – the infamous model, actress, and reality TV personality. She was one of the most famous women on the planet during the nineties, but somehow everything went horribly wrong. At Hype Galore, we’re revealing exactly what happened throughout her life that lead to such a tragedy.

She modeled herself on Marilyn Monroe, but she had no idea that her life would turn out to be equally as tragic. From her surprising rag to riches background, to marrying an 89-year-old billionaire while in her twenties, her extraordinary story will show you a side to Anna that few people know about.

She Was Only 17 When She Got Pregnant From Her Fried Chicken Shop Co-Worker

Texan-born Anna came from an impoverished background and ended up dropping out of high school in her sophomore year, after having failed her freshman year. She was working at Jim’s Krispy Fried Chicken, and soon started a romantic affair with her co-worker, Billy Wayne Smith. He was working as a cook at the fast-food chain.

She didn’t have her famous blonde hair yet but she was clearly a natural beauty. They got married in 1985 when she was only 17 years old and Billy was 16, and the following year she gave birth to their son, Daniel Wayne Smith. While she loved her son, this wasn’t the life that she wanted, and a few months after their baby boy came into this world, they separated.

Changing Her Image To Look More Like Her Idol: Anna Wasn’t Born Naturally Blonde and She Went Under the Knife

After leaving Billy she dyed her hair peroxide blonde like her idol Marilyn Monroe. It was Marilyn who made Anna want to become an actress, so much so that she admitted to traveling around with a selection of Monroe movies in her bag, even after she became famous! In this photo, Anna’s goofing around with her mom Virgie at home.

But her hair color wasn’t the only thing that changed. She went under the knife and had cosmetic surgery to enlarge her breasts, and it later became a huge part (pun intended) of her public image. “Until after I had my son, then I went way out,” she once revealed when talking about her 36-28-38 measurements. “They have so many different stories, nobody’s gettin’ anything right.”

Fed Up of Working in Food Service, She Started Stripping to Support Her and Her Son

The truth was, Anna had a whole bunch of jobs before finding fame. She wasn’t working at the fried chicken shop anymore but supported herself and her son by working at places like Red Lobster and Wal-Mart. That’s until she discovered that she could be making more money stripping.

According to a former psychiatrist of Anna’s, she had a borderline personality disorder but it went by unnoticed at the time. Anna struggled with substances later in her life but she generally stayed out of trouble. That is, when she wasn’t getting arrested for drunk driving as she did in 1989…

Playboy and Hugh Hefner Gave Anna Her Big Break Into Modelling and Eventually Movies

In the early nineties, a friend of Anna’s sent her photo to a Playboy scout, and she was asked to star in the March 1992 issue. For a small-town girl, it was quite hard to believe: “Around 1992, my uncle called me and said, ‘[Anna]… made Playboy.'” She continued: “I was like, ‘What?’ He said, ‘She made Playboy.’ And I said, ‘She did not.’ And he said, ‘Yes, yes, I promise. Get the magazine.'”

Anna was the Playboy Playmate of the Month by Mr. Hugh Hefner himself, and she was over the moon. It was her big break into Hollywood, as after the issue came out she was asked to model several top brands and publications. The likes of Guess jeans, Marie Claire, GQ, and New York Magazine hired her for their billboards and front covers.

She Met Her Future Husband While She Working In a Strip Club, But He Was 63 Years Her Senior

In 1991, Anna was working in a strip club when she met the elderly oil tycoon J. Howard Marshall, AKA James. She was a young 23-year-old and he was 86. It was the start of a two-year-long affair filled with expensive presents, big promises, and a lot of proposals.

He wanted her all to himself despite their huge age gap of 63 years, and Anna eventually came to a decision about whether or not to marry the tycoon. She would later admit: “I was 23, and he was 86. I saw a very sick man. I just wanted to just talk with him. There was no physical attraction at all. He was very much attracted to me.”

At 89 Years Old, James Howard Marshall Weds His Shockingly Young Bride

In 1994 Anna agreed to marry James, resulting in one of the most iconic photos of all time. Anna was a stunning young bride standing tall as she recited her marriage vows to the sleepy oil tycoon. Unsurprisingly, everyone from the media to the public accused her of being a gold-digger.

But Anna insisted that she did marry him out of love and not for his massive fortune. In a later interview at the turn of the century with ABC News, she explained how James “took me out of a terrible place and he cares for me and my son, and in return, I took care of him, and I loved him for that.”

The Oil Tycoon’s Death Was the Start of a Very Messy Legal Battle

Whether or not Anna was gold-digging, James passed away the following year leaving behind his hefty fortune. Anna wasn’t written into his will, claiming that her husband had intended to set up a trust fund for her like he had done before for family members. She had no idea about what really lay in store for her.

But because nothing was in writing, Anna had to sue the estate. She was asking for half of his $1.6 billion fortune, and James’ family (particularly his son Everett Pierce) were furious. Anna stood firm on her claim that it was what her husband would have wanted or, at the very least, he wanted her to get a piece of the pie. But James’ family members were adamant that Anna should get absolutely nothing.

One of Anna’s Interactions With James Is Called Into Question As She Went Against Doctors Orders

The son Everett Pierce already had reason to suspect Anna of foul play. A few months into their 14-month-long marriage, the oil tycoon’s health started to drastically deteriorate due to stomach cancer. But there had been one night before the diagnosis that Anna had gone against the doctor’s orders and fed James soup with a spoon.

It may not sound like much at first, but James’ doctors had specifically ordered him only to eat through a tube. They feared that being spoonfed could cause him to choke, and that’s exactly what happened. The night Anna spoonfed him, he ended up passed out in an emergency room having to be revived. Because of that night, James’ furious son Everett won guardianship over his dad.

Anna Defended Their Unlikely Love Story and Claimed She Hasn’t Been With Anyone Else Since Him

Anna claimed that the love in her marriage was real. In 2002 she told Larry King “I loved him for so much for what he did for me and my son,” adding that “I’ve never had love like that before. No one has ever loved me, and done things for me, and respected me and didn’t care about what people said about me.”

As far as she was concerned, she wanted to fulfill her recently deceased husband’s wishes and at the time stated: “I’m going to fight until the end. My husband is worth it. He wanted me to have it. He was worth a lot. He was a very, very wealthy man.” She even went so far as to say that she hadn’t been with anyone since. “I have been alone since my husband died. I stay in my home. I don’t date. It’s hard to date when you’re at home. Nobody knows you.”

Anna Gets Sued by a Former Nanny at the Worst Possible Time, Forcing Her to Go Into Debt

Anna couldn’t catch a break. As the legal battle began, a woman came forward claiming to have previously been a nanny to Anna’s son Daniel. And according to her, Anna had engaged in very inappropriate behavior with her and essentially harassed her. The former nanny said illegal substances were involved, and unconsenting acts took place. But Anna claimed that everything had been consensual.

The former nanny was looking to bag $2 million. In the end, she walked away with $800,000 by default, as Anna had failed to attend any of the legal hearings. This was a terrible blow coming at an awful time, and Anna was forced to file for bankruptcy. She listed herself as having a debt of $9 million and did so in California, as she was living there at the time. But as we’ll later see, Anna would deeply come to regret that decision.

A Furious Everett Lifts the Lid on the Reality of Their Relationship, Bringing Up Those Expensive Gifts

As far as James’ son Everett Pierce was concerned, Anna had already been given her fair share of fortune by the 86-year-old man. He was adamant that his father had already been exceedingly generous to the aspiring model and actress. James spoiled Anna to a very extravagant lifestyle.

But there was more; according to Everett, his father had showered her with pricey gifts. She had been showered in millions of dollars worth of jewelry, including one shopping trip that saw James buy her $2 million dollars worth of jewels at once. He had also kindly gifted the model a flashy red Mercedes and a Rolls Royce, as well as included her on his company’s health plan and payroll.

Anna Turns To Painkillers To Help Her Cope With Having No Money and Being Badly In Debt

Anna was still only in her twenties but already her life was falling apart. She was a single mom with no money who was heavily in debt, and because of that, she ended up forming a dependence on painkillers. It wasn’t long before Anna ended up overdosing and ending up in a coma.

Once she came out of the coma she did the smart thing and checked herself into the Betty Ford Rehab Center. But she suffered a breast implant rupture and had to have reconstructive surgery, which was a painful ordeal. She ended up going back to her painkillers and lapsed all over again.

Her Movie Career Comes To An Abrupt End After Hollywood’s Biggest Talent Agency Drops Her

As if things couldn’t get any worse for Anna, she got dropped by the prestigious agency who had been representing her since her Playboy magazine spread, William Morris. They were one of the biggest talent agencies in Hollywood, so losing them was a huge blow to the aspiring actress.

She had been starring in some movies like Naked Gun in 1994 and To the Limit in 1995. But the latter would prove to be her last movie of the decade as her public image was plummeting. She only went on to shoot one more film during her life, but it wasn’t released until after her death.

Anna Reveals How Everett Stopped Her From Spending Time With Her Husband When He Became the Legal Guardian

Anna claimed that Everett Pierce cut her off both financially and physically while James was still alive. Everett had become his father’s legal guardian after he was hospitalized, and he only allowed Anna to visit the oil tycoon for up to 30 minutes at a time. In 2000, she told ABC News “After my husband passed, it was really, really hard on me.”

She continued: “He knew me when I was nobody and that’s what people don’t understand, and I don’t wanna be called a gold digger because I’m not. I could’ve married him a week after we met, or two weeks after we met. I could’ve married him years before, and I didn’t. I didn’t. I went out and I made something of myself.”

Love Is In the Air For Anna and the Attorney Who Had Been Representing Her In Court, Howard Stern

Anna met attorney Howard Stern in 1998 while she was fighting for her deceased husband’s estate. He was just one of many who were hired to represent her, but they quickly developed more than just a professional relationship. They fell for each other, started hooking up, and began a long-lasting love affair.

But Howard wasn’t the only man Anna was seeing, and we’ll come to see that later this would come back to haunt him. “I loved Anna and I cared for her so much. I have no regrets,” he later revealed. And we’re not surprised, considering how he left behind his successful law career to co-star with Anna on her upcoming reality show.

A Cable Network Gives Anna Her Very Own Reality Show Due To the Public’s Interest In Her Personal Life

In the early 2000s, Anna was given her own reality TV show by E! cable network that was going to focus on her personal life. While her acting career was going nowhere, the public’s interest in her troubled private life was bigger than ever and when the show finally premiered, it saw the highest cable rating for a reality TV show yet.

Controversially, the show premiered on the death anniversary of her late husband James… and it starred her new attorney boyfriend Howard Stern and her son Daniel. Suffice to say the public had a lot to say about it. From the confusing professional-yet-romantic relationship she appeared to have with Howard to her slurred words, people couldn’t wait to see what came next for Anna.

Anna Makes An Appearance In Kanye West’s Music Video For His 2004 College Dropout single, “The New Workout Plan”

In 2004 Anna was still in the middle of the legal case, but she somehow found herself starring in Kanye West’s College Dropout single, “The New Workout Plan.” Her role was to play the “ultimate trophy wife,” which was pretty much becoming her brand and persona.

She was becoming more famous for her crazy antics and messy lifestyle than any significant acting work and is thought by many to have paved the way for the future of other reality stars like Kim Kardashian and Paris Hilton. Sadly, she was being used by Hollywood.

A Massive Wardrobe Malfunction Happened at the G-Phoria Awards in 2004, but Anna Just Shrugged It Off

And Anna’s public image only got messier. Also in 2004, she suffered a major wardrobe mishap when she accidentally flashed her breast while on stage for the entire audience to see. It’s many people’s literal worst nightmare and for good reason, and many would have felt deeply embarrassed.

We’re not sure how that happened exactly but either way, Anna didn’t seem to care too much. Part of her image was to seem totally unbothered and always up for fun, regardless of the situation. And even while she was meant to be at her most glamorous at the G-Phoria Awards, she struggled to keep it together.

There’s a Baby on the Way But Only Anna Knows Who the Biological Father Is

By 2005, Anna had fallen pregnant with her second child, but she refused to tell the public who the father was. Howard Stern claimed that he was the biological father, adding: “We love each other, and it’s been going on for a very long time, and because of my relationship as her lawyer, we felt it was best to keep everything hidden.” The real father was a celebrity photographer called Larry Birkhead, who Anna had been dating on and off for a while.

In the meantime, Anna’s body was changing and she had a difficult time of it while living in the public eye. “It’s hard. I mean, I went through a lot. You know, people, when I gained a lot of weight… people thought I was just like, partying, doing this and that,” she had said earlier. “I mean, I’m having seizures, I’m having panic attacks. My husband just died and people think I don’t care.” Clearly, Anna was in a bad place mentally.