Inside Anna Nicole Smith’s Romance with 89-Year-Old Howard Marshall

Smith was a larger-than-life blonde from Houston who caught the eye of men as a ‘Playboy’ Playmate of the Year.

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Anna Nicole Smith was a larger-than-life blonde from Houston who caught the eye of men as a Playboy Playmate of the Year and became a tabloid sensation until her untimely, tragic death.

But perhaps more than anything else, the 6-foot-tall model made headlines for marrying 86-year-old billionaire and oil magnate J. Howard Marshall.

So, how did the marriage come about — and what ended it? Here’s the story.

The Many Romances of Anna Nicole Smith

Before tying the knot with Marshall, Anna Nicole Smith got an early initiation into adulthood. She struck up her first real romantic relationship when she met fry cook Billy Wayne Smith while they worked together at Jim’s Krispy Fried Chicken.

At 17 years old, she married Smith — who was actually a year younger than her. After giving birth to their son, Daniel Wayne Smith, in January 1986, Smith and her husband separated. Their divorce was eventually finalized in 1993.

That same year, Playboy crowned her as its Playmate of the Year. Around the same time, she replaced supermodel Claudia Schiffer as a model for Guess jeans.

It was 1994 when she married Marshall, whom she had met while stripping at a Houston club a few years prior. He apparently showered her with pricey gifts and asked for her hand in marriage multiple times.

Anna Nicole Smith was Marshall’s third wife after two previous wives, with whom he spent 30 years each.

The marriage of Smith and Marshall became the stuff of tabloid legend. The general public seemingly accepted that Anna Nicole Smith had only married Smith for his money, a claim she vehemently denied for many years.

Most famously, perhaps, a photo capturing Marshall smiling ear to ear as Anna Nicole Smith seemingly posed awkwardly beside him.

Fourteen months after marrying Smith, Marshall died in August 1995 at age 90. Litigation ensued, with one of her court battles over Marshall’s estate going all the way to the U.S. Supreme Court.

All the while, Anna Nicole Smith became even easier tabloid fodder after making numerous appearances and comments that raised concerns about her use of drugs.

Most notably, she appeared heavily intoxicated when presenting at the American Music Awards in November 2004.

Smith had achieved a level of fame that presented her with acting roles and a reality-TV show. Unfortunately for her, critics did not shower Smith with praise for her performances.

Smith’s Sad Outcome

Meanwhile, the public eye witnessed Anna Nicole Smith’s life spiraling out of control. Dark days lied ahead for her.

Smith became romantically involved with attorney Howard K. Stern but did not marry him. Instead, they exchanged vows and rings during a commitment ceremony.

Smith’s life took a turn for the worse when her son Daniel Wayne Smith died of a drug overdose at 20 years old, in September 2006. She was supposedly so devastated that she tried to climb into her deceased son’s coffin during funeral services.

Anna Nicole Smith died in January 2007 at a hotel in Florida. Authorities found 11 drugs in her system, many of which belonged to Stern, according to TMZ.

Smith’s lasting legacy was litigation. In the years following her death, Smith’s mother sued various tabloids and news organizations for defamation. 

Another one of her romantic interests, entertainment photographer Larry Birkhead, eventually got custody of his child with Anna Nicole Smith, Dannielynn Birkhead.

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