Marrying The Billionaire Single Dad

[Catherine Rubeo]

Therichest 10 single billionaires have an average age of 54.5. The youngest bachelor in the list is 31 years old: Scott Duncan, who is worth $5.3 billion and is son of the late energy mogul Dan Duncan.

Allen lives on Seattle's Mercer Island, but he recently bought a $27 million, eight-bedroom mansion in the Silicon Valley town of Atherton, which has the most expensive zip code in the U.S., according to Forbes.

quicklist:title: Marcos Mera, 42media: 21095839category: $5.7 billion text: Marcos Mera, 42, inherited the wealth of his late mother, Rosalia Mera, when she died in August. She was the world's wealthiest self-made woman from co-founding Spanish clothing brand Zara. The family's holding company is Rosp Corunna Participaciones Empresariales. Marcos Mera's sister, Sandra Ortega Mera, inherited more than 90 percent of their mother's wealth and became Spain's richest woman.

quicklist:title: Alejandro Santo Domingo Davila, 36media: 21095439category: $3.9 billiontext: Alejandro Santo Domingo Davila, 36, a Harvard graduate who is the second-richest person from Colombia, inherited the wealth from his father, Julio Mario Santo Domingo Pumarejo, who died in 2011. The Santo Domingo Group has interests in a range of businesses including SABMiller.

Maybe a day after then-married socialite Mercedes Bass threw a dinner roll across a crowded ballroom at then-married billionaire oil heir Sid Bass in June 1986, the two began conducting the kind of affair that very rich people conduct:

Sid and Mercedes taking a private jet to Paris, cocooning themselves at the Plaza Athne. When they finally venture outside, they strolled through the streets hand-in-hand, sure that no one they knew would see them. Until, of course, someone they knew saw them.

Sid has three younger brothers, but he was the Chosen One, and when his father stepped down from Bass Brothers in 1968, the Yale-educated Sid took over. It was his investment strategy that transformed the company into a billion-dollar operation.

So by the time Mercedes, described by many who know her as a worldly, sophisticated woman, teased Sid Bass at that ball, and he hurriedly scrawled down her phone number before his wife could see, both were deeply unhappy.

Mercedes took to her role as Mrs. Sid Bass with alacrity and ease, spending more than $75 million for homes in New York and Fort Worth. There were originally four houses on the Texas property; the couple combined two of them, and Mercedes had a third, which she deemed unsightly, picked up and sent across town to serve as a home for single mothers. According to the Dallas Morning News, once she realized the house across the road had a view into their property, she had Sid buy them, too.

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.

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.

"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."

"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 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'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.

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.

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