Anna Nicole Smith’s Dating History: From J. Howard Marshall II to Larry Birkhead

After the death of her husband in 1995, Anna Nicole Smith was linked to Larry Birkhead and Howard K. Stern before she died in 2007

Anna Nicole Smith lived a very public love life.

Before her unexpected death in February 2007, Smith was married twice, perhaps most notably to her second husband, oil tycoon J. Howard Marshall II. However, their 1994 union was met with plenty of criticism: When they married, he was 89 and she was 26.

When Marshall died about 14 months later, he allegedly left Smith out of his will and gave his entire billion-dollar estate to his son, E. Pierce Marshall. A lengthy legal battle between Pierce and Smith and Marshall's oldest son, J. Howard Marshall III (who was also left out of the inheritance) ensued, though a court eventually ruled in 2010 that Smith's estate was not entitled to any money from Marshall's estate.

Through this legal battle, she met lawyer Howard K. Stern, whom she was linked to up until her death at age 39. Smith also struggled with substance abuse during the last decade of her life. Her son Daniel (whom she shared with her first husband, Billy Smith) died in September 2006 of a drug overdose, just days after she gave birth to daughter Dannielynn. In the months between Dannielynn’s birth and Smith’s death, she was involved in a battle over the paternity of her daughter: though her lawyer-turned-partner Stern was listed on the birth certificate, former flame Larry Birkhead claimed he was Dannielynn’s real father.

After her death of an accidental overdose on Feb. 8, 2007, DNA evidence confirmed that Birkhead was Dannielynn's biological father.

In May 2023, Missy Byrum revealed to PEOPLE that she was in a secret romantic relationship with Smith for several years in the early 1990s. The pair, who met at a strip club in Houston, raised Daniel together and eventually got married (though, it was not legally binding).

"I was not her first female lover," Byrum said. "But I knew it would not last. She needed more love than any one human being could give her."

Related:All About Anna Nicole Smith and Larry Birkhead's Daughter, Dannielynn Birkhead

From her two marriages to her daughter's paternity case, here's a look back at Anna Nicole Smith's former relationships.

Billy Smith

Smith grew up in Mexia, Texas as Vickie Lynn Hogan. She married Billy Smith in 1985 when she was 17 and gave birth to their son Daniel when she was 18. Their marriage was short-lived, however, as the couple divorced in 1987.

Missy Byrum

During an interview with PEOPLE in May 2023, Smith's friend Byrum revealed that she and Smith, whom she calls Nicki, had a secret romantic relationship. The pair met in the late 1980s while working at a strip club in Houston and quickly became best friends.

"I was not her first female lover," Byrum said. "But I knew it would not last. She needed more love than any one human being could give her."

For years, Byrum helped raise Smith's son, Daniel.

"Nicki was getting more dependent on me because I'm taking care of Daniel while she's gone. And then I'm traveling with her all the time and so we're together all the time," she explained. "We became lovers, you know? And I mean real sober lovers — it was a conscious thing. She said that she loved me."

In 1993, Smith proposed to Byrum and the couple married in their backyard, though it was not a legally officiated ceremony.

"I wore the rings. She wanted me to have a baby with her. But I always knew it wasn't ever going to work out. Because she was never, ever going to settle down with one person," Byrum shared.

J. Howard Marshall II

In 1991, Smith met oil tycoon J. Howard Marshall II while she was working at a strip club in Houston. They wed on June 27, 1994, when he was 89 years old and she was 26. It was the second marriage for Smith and the third for Marshall, who was confined to a wheelchair.

By that time, Smith was already a supermodel, featured as the 1993 Playboy Playmate of the Year and in blonde bombshell Guess ads, and had appeared in the films The Hudsucker Proxy and Naked Gun 33 ⅓. As soon as the ceremony was over, Smith jetted off to Greece solo for a modeling assignment.

Many questioned Smith’s motivation in marrying the elderly billionaire, but she always maintained that they truly had a romantic connection. “I know people think I married Howard for his money,” she said. “But it’s not true. I love him.”

Marshall died on Aug. 4, 1995, less than 14 months after their wedding. The rift between Smith and Marshall’s son Pierce was evident in Marshall’s funeral arrangements: they hosted separate services for the oil tycoon.

Related:Larry Birkhead Gets Real About Living in the Shadow of Anna Nicole Smith's Late Billionaire Husband

At Smith’s service for her late husband, her attorney Diana Marshall (no relation) said, “I am here today to talk about love. I have never known a relationship that embodied love as much as this one. Anna, if Howard were here today, he would say to you, ‘Don’t cry, Precious Package, my Lady Love.’ And in years to come, when you see yourself succeeding, as you will, because you are strong, you will say to yourself, ‘Hello, Howard, I’m succeeding, I’ve got my chin up.’ ”

Smith’s devotion to her late husband lasted for the rest of her life. “Of all the people that she'd talk about the most, it would be her late husband,” Birkhead told Wendy Williams in 2017. "You kind of had to live up to this guy. You would roll over in bed and there was an oil painting of him over on one side. You'd roll over to the other side and there was a picture of him on the dresser. If you got into an argument with her, she would say: 'Why can't you be more like my husband?' And I'm like: 'Well, I didn't strike oil yet!' "

Christian Audigier

Smith met Christian Audigier, the fashion designer behind Ed Hardy and Von Dutch, at a party sometime in 1998.

“I met Anna Nicole Smith at a party for Gerard Guez,” Audigier later told Los Angeles Magazine in 2009. “She was dressed up like Marilyn Monroe to wish him a happy birthday. She was pretty back then. I flirted with her, using my four words of Frenglish.”

According to Audigier, the pair dated for six months.

Prince Frederic von Anhalt

The model reportedly first met Prince Frederic von Anhalt — Zsa Zsa Gabor’s ninth husband — in New York in the 1990s. He claimed that the two began an affair shortly after meeting.

In 2007, von Anhalt made headlines when he publicly claimed to have fathered Smith's daughter Dannielynn during a press conference held on the driveway of his and Gabor's Bel Air mansion. However, DNA tests later proved his paternity claim to be false.

Larry Birkhead

Smith met Larry Birkhead, a photographer and real estate investor, at the Barnstable Brown Gala in May 2003, an annual event held the night before the Kentucky Derby. Birkhead said he was attracted to the real woman, not her public persona.

"There were two different personalities," he said on The Wendy Williams Show in 2017. “The Anna Nicole that everyone saw was kind of more an act — she would put this different voice on, it was like a baby voice ... but she was always in on the joke.”

Birkhead said he fell for her other side. “I came to know her at some events away from the camera ... with no makeup on, just hanging out with all the kids and giving money and time [at charity events] — things that you don’t hear people talk about when they talk about Anna,” he said. “And that’s kind of when our relationship grew.”

Smith and Birkhead went on to welcome one child together, Dannielynn, though the baby's father was originally thought to be Smith's partner Howard K. Stern. She was born Dannielynn Hope Marshall Stern on Sept. 6, 2006, in the Bahamas, where Smith had recently moved to escape scrutiny from the press. While visiting his mother and Dannielynn in the hospital, Smith’s son Daniel died of an accidental drug overdose in her hospital room on Sept. 10, 2006.

Though Smith and Stern claimed they were the parents of Dannielynn and were listed as such on her birth certificate, Birkhead claimed to be the baby's real father and filed a paternity case in October 2006.

During the paternity case over Dannielynn, Birkhead’s attorneys filed testimony and paperwork from a friend of Smith’s, Laurie Payne. She described a “love-hate” relationship between Smith and Birkhead and claimed that Smith had become pregnant earlier in their relationship but suffered a miscarriage. Among the papers filed was an email from Smith talking about being estranged from Birkhead during the pregnancy, writing, "No one’s happy for me, so how can I be, and that’s so sad, cause it’s all I ever wanted, but not alone."

Two months after Smith's death, a DNA test confirmed that Birkhead was Dannielynn's father. Dannielynn was named sole heir to her mother’s estate, and Birkhead was awarded full custody.

Now, Birkhead and Dannielynn attend the Barnstable Brown Gala annually. In 2023, Dannielynn’s outfit was emblazoned with images from Smith’s iconic Guess modeling campaigns, and Birkhead wore a tie to match.

"She's showing off her fashion sense but at the same time paying tribute to her mom," he told PEOPLE ahead of the event. "We're both paying tribute [to Smith] because it's the 20th anniversary of our first meeting."

"It seems like yesterday to be honest," Birkhead added. "That I was walking up with my camera bags and just hoping for a decent picture. I wound up with so much more. It's funny how one event can change your life. And that's what this party did for me. If I had not been there that night and had that connection, how different my life would have been if I hadn't met Anna and had our daughter."

Howard K. Stern

Howard K. Stern met Smith when she hired him as her legal counsel in her case against E. Pierce Marshall regarding her late husband’s estate. Stern and Smith became very close over the ensuing years, to the point that Stern was a regular fixture on The Anna Nicole Show that aired on E! from 2002 to 2004.

Stern also became her business manager in addition to her legal counsel, with Smith paying his living expenses. Eventually, they became closer.

“I wanted more than a lawyer relationship, and then started kind of flirting with him and we kind of got it on,” Smith once told Entertainment Tonight. “I just kind of attacked him and that was it. I kissed him first. He was the shy one. He was like, ‘I can’t, I can’t,’ because he always had to go by the books. I knew I was in love the first time I kissed him.”

When Smith's only daughter Dannielynn was born in September 2006, the model claimed that Stern was the father. However, a DNA test several months later proved otherwise.

Shortly after Dannielynn's birth (as well as the death of Smith's son Daniel), Smith and Stern held a commitment ceremony on a boat in the Bahamas on Sept. 28, 2006. Though they exchanged vows, they weren’t officially married.

“Anna was his entire world,” Smith’s former assistant Kim Walther told PEOPLE.

Following Smith's death in 2007, Stern and two others were arrested and accused of helping Smith get prescription drugs in illegal ways. Though he pled not guilty, a jury found Stern guilty of two counts of conspiracy. However, a Los Angeles judge later dismissed the felony charges against him, ruling that there was no evidence of intended fraud or deception.

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