Anna Nicole Smith and oil tycoon J. Howard Marshall. Anna was a 24-year-old stripper when she met the 86-year-old billionaire.
While performing at a Houston strip club in October 1991, Smith met 86-year-old petroleum tycoon J. Howard Marshall.
During their two-year affair, Marshall reportedly lavished expensive gifts on Smith and asked her to marry him several times.
On June 27, 1994, Smith and Marshall were married in Houston, resulting in speculation that she married him for his money.
She maintained that she loved Marshall and that age did not matter to her.