Kim Basinger – Bankrupt Celebrities
Kim Basinger, actress and ex-wife to Alec Baldwin, bought the town of Braselton, Georgia for $20 million in 1989 -- only to sell it for $1 million when she ran into financial trouble just a few years later.
(Maybe because she bought an entire town for $20 million.)
She filed for bankruptcy in 1993 when she was ordered to pay $8.1 million (later reduced to about half that) to Mail Line Pictures for backing out of the film 'Boxing Helena.'
Which, in hindsight, was a pretty good decision, although maybe not millions of dollars good.