Anna Nicole Smith and J. Howard Marshall

She was a well endowed stripper working a Texas chicken fast food joint and he was an 89-year-old Texan billionaire. The unlikely couple married in 1994 much to the chagrin of everyone with a functional pair of eyes and put up a mighty good show of their coupledom too! We would've expected it from Hugh Hefner perhaps but Marshall was a respected businessman. 

Unfortunately for Anna, the bank account she fell so head-over-heels in love with didn't quite return the sentiment because she found she wasn't in the will when Marshall kicked the bucket soon after. A battle over his estate ensued and one judge even awarded her $475 million. Having said that, it's not entirely surprising that she was left out of the will considering Smith left for Greece with her bodyguard immediately after the wedding!