#6: Sammy Davis Jr.
Singer, dancer, actor, comedian: Sammy Davis Jr. could do it all. As a member of Frank Sinatra’s famous Rat Pack, he broke racial barriers and sold out shows for decades. He loved to spend money, and he gave it away generously to the people around him.

Behind all the glamour, his tax bills were quietly piling up. When Davis died of throat cancer in 1990, he reportedly owed the IRS more than $5 million. His widow was left to deal with the debt, and many of his belongings ended up sold at auction.
