#11, Howard K. Stern and Anna Nicole Smith
Theirs was a union marred by tragedy. Stern first crossed paths with Smith when his law firm handled her modeling contracts in the early 1990s, and again when Smith fought with the sons of her late husband, J. Howard Marshall, over the octogenarian's fortune. Stern soon left his law firm to become Smith's agent of sorts, co-starring with her on
The Anna Nicole Show
. The two eventually became romantically involved, and when Smith had a daughter, Dannielynn Hope Marshall Stern, on Sept. 7, 2006, the birth certificate recorded the father as Howard K. Stern. The couple exchanged vows in a non-legally binding ceremony on a boat near Nassau a
few weeks later
. After Anna Nicole Smith died from a drug overdose on Feb. 8, 2007, Stern was initially granted custody of Dannielynn, until it was revealed following a long paternity case that photographer Larry Birkhead was the biological father. Oh, and it got worse. Stern, along with doctors Sandeep Kapoor and Khristine Eroshevich, were charged with prescribing and administering drugs to Smith. Stern and Eroshevich were both found guilty of the charges on Oct. 28, 2010,
according to CNN
, with each facing up to three years in prison.