Anna Nicole Smith left her mark in some unexpected places.
Following an impoverished upbringing in small-town Texas she became one of the most famous faces of the '90s as a Playboy cover girl and Guess model. She had a reality show before television was overrun with reality shows. When she was 26, she married an 89-year-old billionaire whom she'd met while stripping. And in 2006 she ended up at the United States Supreme Court while still fighting for her inheritance 11 years after her husband died.
Her rise to fame may have come as a surprise to those who knew Vickie Lynn Hogan as a kid in Mexia, when she dropped out of high school at 15 and went to work at a fast-food chicken restaurant.
And like Monroe, Smith never made it out of her thirties.
Smith—born on Nov. 28, 1967—used to travel with a handful of Monroe films in her bag. She admitted to having four of them with her on a trip to New York during a 1993 appearance on Live With Regis and Kathie Lee.
Asked if it was true that she hadn't "blossomed" until after the junior prom, Smith smiled and said, "No, until after I had my son, then I went way out," referring to the 36-28-38 measurements that made her such a memorable centerfold. "They have so many different stories, nobody's gettin' anything right."
At the moment she was referring to the origin story of her bombshell curves, but in hindsight it was an eerily prescient observation about the days ahead, when people would cease to see the person amid the trappings of excess that soon surrounded her.
Her parents, Donald Hogan and Virgie Arthur, divorced in 1969, and when her mother remarried Donald Hart, Vickie Lynnn changed her name to Nikki Hart. She dropped out of high school and married Billy Wayne Smith in 1985, when she was 17. They welcomed their son Daniel Smith on Jan. 22, 1986.
Statuesque at 5-foot-11, she went from 125 pounds to 211 pounds during her pregnancy—but she couldn't answer Kathie Lee Gifford's plea for information when the host asked how she lost the weight "in all the right places" and ended up with her enviable proportions. "I don't work out," Smith responded sheepishly.
Her big break came when she landed the March 1992 cover of Playboy (then going by Vickie Smith) and in 1993 Hugh Hefner named her Playmate of the Year.
Guess founder Paul Marciano remembered his first meeting with Smith, soon after her Playboy debut, in a July 2017 interview with Paper magazine.
"I found her in San Antonio. I was shooting GUESS Kids and she came with her son Daniel," he said. "I said, 'Who are you?' She said she was a waitress at Red Lobster. Everything I asked her she called me 'sir.' She had never done pictures before. I had the kids' photographer shoot her on the spot. I took her to New York and got her an agent and changed her name. To me, she was Anna, but Anna Smith did not sound right so we did Anna Nicole Smith."
Smith succeeded Claudia Schiffer as the face of the brand, promoting a refreshingly real (although still unreal) body type among the grunge-era waifs so in fashion at the time.
"I think a lot of women can relate to my size," Smith—who started calling herself Anna Nicole when shooting her first Guess campaign—agreed on Live in 1993.
She had also just kicked off her acting career with one line in The Hudsucker Proxy—and she had reunited with her biological father for the first time since her parents' divorce in 1969, enlisting a service called Birth Parents to track him down, which they did in about a week. Using her maiden name and not revealing who she was, Smith flew him out to L.A. "He goes, 'oh my god, I've looked at you,'" she recalled, laughing and also wincing a bit in embarrassment. "In the Playboy," she clarified to a speechless Regis and Kathie Lee.
"She was living the dream," Larry Birkhead, Anna Nicole's former boyfriend and father of her daughter, Dannielynn Birkhead, reminisced to ABC News in 2017. "Here she is, a little girl from Texas, went from working in a chicken shack to making movies with big stars in Hollywood."
Smith's star was indeed on the rise. But it was barely a year later when her Cinderella story took an irrevocable turn for the weird.
Smith and husband Billy divorced in 1993 and the following year she married Texas oil tycoon J. Howard Marshall, whom she had met years beforehand when she was working at a strip club and who was 63 years her senior. She insisted she married him for love, not money. She told ABC News in 2000 that Marshall "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."
Marshall died in 1995 and, much to the outrage of his heirs, Smith sued for half of her late husband's $1.6 billion estate, maintaining that—while he didn't include her in his will—he had intended to set up a trust to provide for her as he previously had set a trust up years before for his family.
Marshall's son E. Pierce Marshall, who inherited almost the entire estate, argued that his father had already been adequately generous to his trophy wife, showering her with gifts and treating her to a lavish lifestyle.
A sexual harassment suit filed against Smith by her son's nanny resulted in a $800,000 judgment against her after she missed several depositions, resulting in Smith filing for bankruptcy in California. Pierce then filed a defamation claim against her bankruptcy, angry at her claims that he had interfered with his father's intentions and prevented him from setting up the trust for Smith, isolating the old man in the process.
Broke and in debt, Smith was taking huge amounts of painkillers and ended up in a coma after an overdose. She checked into the Betty Ford Center to get clean but by early 1996 she had fallen off the wagon. According to a 2011 New York magazine profile, one of her nipples tore after a breast implant ruptured, and the pain of reconstructive surgery resulted in her going back on painkillers.
Around this time she was dropped by her agency William Morris and she signed up for representation with a small Beverly Hills legal firm. One of the partners was attorney Howard K. Stern, who would factor into Anna Nicole's story forever after.
In October 2006, a federal bankruptcy judge in California sided with Smith, agreeing that Pierce had purposely tried to keep her away from Marshall's money, and awarded her $449 million, plus $25 million in damages from Pierce; the amount was later reduced to about $88 million. A trial underway in state probate court in Texas, however, would soon result in Smith being awarded nothing. Because the bankruptcy court was trying to assert its ruling over the state court, Pierce appealed to the U.S. District Court in Los Angeles, which shrank the award to $88 million, in accordance with Marshall's supposed promise to leave Smith half of what he earned during the time they were together.
Not good enough for Pierce. He took it to the 9th Circuit Court of Appeals.
The case would drag on, but in the meantime, Smith's drug troubles and the media circus over these legal proceedings (not to mention her marriage in the first place) had etched away at her glamour-girl status.
She had a memorable role as the bad guy's seductive girlfriend in Naked Gun 33 1/3 in 1994 and starred as an ex-CIA agent in the 1995 B-thriller To the Limit, but that was the end of her movie career in the 1990s. She wouldn't shoot another film until Illegal Aliens, which came out after she died at the age of 39 on Feb. 8, 2007, of an accidental overdose of prescription drugs.
"She had such a magnetic personality, but you could see that she was fragile," Marciano told Paper. "Success came and she got recognized by people. She started taking sleeping pills because she couldn't sleep and mixing alcohol with them. I stopped working with her because I couldn't deal with that. I said, 'We're done.' After that she met the wrong people, and I think that was it."
By the time she starred in The Anna Nicole Show on E! in 2002, she had turned into a pop culture curiosity. The show only lasted for 14 episodes, but the scenes of a barely coherent Smith slurring her words, saying some unintentionally hilarious stuff and attending to her day-to-day affairs as if she was under water would linger. She soon became known more for her antics than for any straight-forward career move.
At the G-Phoria Awards in 2004, her left sleeve failed her and her entire breast popped out of her dress. Smith covered up with her hand but didn't appear too concerned. Also that year, she appeared in the video for Kanye West's "The New Workout Plan," which made it at least slightly understandable when she memorably asked, "Like my body?" at the Billboard Music Awards before haltingly introducing the "freaking genius" rapper.
In 2005, she entered a wet T-shirt contest at a club called the Freaky Tiki in Myrtle Beach, S.C.., and reportedly ended up in a screaming match with Birkhead, who was identified as her boyfriend. Stories about the fracas ended up on Smith's own website before being taken down.
"The reason we took down the postings," Stern later told MSNBC.com's The Scoop, "was that we don't want Anna defamed on her own website." To set the record straight, he said, she was wearing pasties, she didn't take, or ask, for pills, and she didn't have a boyfriend.
"The only thing that was true is that I went there to save her because she didn't feel safe," Stern added. "She met some good people in South Carolina and some bad people and I question their motives. I'm glad we got her out of there on time."
Birkhead said on 20/20 that he and Smith were definitely an under-the-radar couple. "No one ever knew one time that I was her boyfriend," he said. "The whole time we dated, if you look at all the video, I'm in the back carrying my camera bag...she didn't want me in the spotlight."
All the while, Marshall vs. Marshall was still raging. The U.S. Court of Appeals had agreed with Pierce, that Smith was entitled to nothing. Her legal team responded by taking their case to the U.S. Supreme Court, which agreed to hear it in 2006.
Smith, having lost 69 pounds since becoming a face of TrimSpa, appeared at the hearing that February with Stern and Daniel at her side. The justices ultimately ruled, 9-0, that Smith's legal fight could continue—meaning her team could again take up the issue of her inheritance with a lower court.
E. Pierce Marshall died four months later and his wife vowed to take up the fight against Anna Nicole ever getting a dime of J. Howard Marshall's money.
But as it turned out, Smith was also pregnant at that Supreme Court hearing.
She retreated to the Bahamas to give birth to daughter Dannielynn Hope on Sept. 7, 2006, at a Nassau hospital. Inexplicably, three days later, Daniel Smith died in his mom's hospital bed, lying next to her. He was 19.
Dr. Cyril Wecht, a pathologist privately hired to perform a second autopsy on Daniel after the initial one was officially deemed inconclusive, told People that Daniel died of a lethal combination of methadone, Zoloft and Lexapro.
Smith was beyond devastated. And in her despondent state, Stern and Birkhead were putting out dueling statements claiming paternity of Smith's baby girl.
"Through it all, even with all the pain, she has been a great mom, a very attentive mom," Stern, who swapped vows in a commitment ceremony with Smith in the Bahamas but never legally married her, said on Larry King Live in the wake of Daniel's death.
"At the funeral, she tried to climb in the casket," Birkhead told 20/20. "I knew that Anna would be in no shape on her own after losing Daniel, as close as they were, to take care of my daughter."
When Smith died five months later, Paul Marciano said in a statement, "Personally, I feel she did not survive the loss of her son Daniel, who was the love of her life."
Smith never denied that Stern was Dannielynn's father, so it would be up to DNA to prove it in a court of law as both he and Birkhead vied for custody of the child in the wake of Anna Nicole's death. (Several other men, including Zsa Zsa Gabor's husband Prince Frederic von Anhalt came forward as possible fathers, too.)
There was also a dispute over the fate of Smith's body, with Stern wanting to decide on her final resting place, too, while Smith's estranged mother, Virgie Arthur, wanted to take her daughter's body home to Texas. Stern won and Smith was buried next to Daniel in the Bahamas.
Birkhead, of course, turned out to be Dannielynn's father and he has devoted his life since to raising that little girl as a single dad. (He told ABC News that Stern had been a supportive friend after paternity was confirmed.)
At 6, Dannielynn appeared in a Guess campaign in honor of her mother. But other than their annual trips to the Kentucky Derby (Birkhead and Smith met while she was shooting her E! show at the Barnstable-Brown Gala that precedes the race), her dad largely keeps his now 17-year-old daughter out of the spotlight.
In 2010, Stern and two of Smith's former doctors went on trial for drug-related charges, at the heart of which was the question of whether the accused had illegally facilitated her with the prescription drugs that ultimately caused her death. Birkhead testified that Smith "would say, 'I'm in pain. I'm not a drug addict.'"
Stern and psychiatrist Kristine Eroshevich were both found guilty of conspiracy but a judge threw all but a misdemeanor charge against Eroshevich out in 2011; he ruled that prosecutors hadn't proved that she and Stern intended to break the law when they acquired meds for Smith using aliases.
An appellate court overturned the judge's decision, but in 2015 the same judge dismissed the charges against Stern yet again.
"I blame him totally for her death," Smith's father, Donald Hogan, told E! News in April 2009, referring to Stern. "Nobody put a gun to her head, but somebody sure brought a lot of drugs home and, instead of bringing drugs to someone, even if she had a fit about it, I'd tell her to tell someone else to get it for you." (Hogan died in September 2009. Virgie Arthur died in 2018.)
In 2011, Smith's case against Pierce Marshall ended up back in the U.S. Supreme Court's hands again—only this time, they closed the book on the 20-year saga, upholding 5-4 an appellate court's decision that the bankruptcy court had no standing to portion out that money to Smith all those years ago. Which in 2011 meant that a nine-figure windfall wasn't in the cards for Smith's only surviving heir, Dannielynn.
Birkhead, noting that he didn't take money from Smith's estate, but rather supported his daughter with his work as a photographer and profits from flipping houses, says that he has raised Dannielynn with the mantra that "excess is not always the best. Be careful who's around you...be good, be caring. Give back. You don't have to be a star to shoot for the stars."
To put it simply, Birkhead wants to keep the best part of Anna Nicole's legacy intact for their daughter and protect Dannielynn as much as is humanly possible, not just from a fate resembling her mom's, but from the pitfalls of the wrong kind of media exposure.
Smith's pop culture legacy, meanwhile, has obviously been more than that of a striking model-actress-reality-star who died too young. Her story had so many stranger-than-fiction twists, it proved ripe for the retelling, be it via TV movies like 2007's The Anna Nicole Smith Story starring Willa Ford and 2013's Anna Nicole on Lifetime with Agnes Brucker; the 2011 opera Anna Nicole; or the 2012 documentary Addicted to Fame, featuring disturbing footage compiled during the making of Illegal Aliens.
But for the better part of a decade there was an audience that had no idea what to do with Smith when she was alive, that only sat back and watched her decline, not knowing what it was exactly that they were watching—and probably figuring that nothing truly bad would happen in the end.
Yet Smith's story didn't have a happy ending. Instead it remains a cautionary reminder that there's always a real person on the other side of that lens.
"The thing about Anna was...it was almost like a split personality," Birkhead said. "Because when the camera was going, she was a whole different thing...that was more, to me, an act than it was the real person, who she was."
(Originally published on Tuesday, Nov. 28, 2017, at 5 a.m. PT.)