1. Abraham Lincoln
Lincoln tried many occupations as a young man, including buying a general store in New Salem, Illinois, in 1832. He and his partner started buying out other stores' inventories on credit, but their own sales were dismal. As the store's debts mounted, Lincoln sold his share, but when his partner died, the future President became liable for $1,000 in back payments. Lincoln didn't have modern bankruptcy laws to protect him, so when his creditors took him to court, he lost his two remaining assets: a horse and some surveying gear. That wasn't enough to foot his bill, though, and Lincoln continued paying off his debts until well into the 1840s.
2. Henry Ford
The enterprise went bankrupt in 1901 and reorganized into the Henry Ford Company later that year. Ford eventually left that group and finally got things right in 1903, when he founded the Ford Motor Company. Things didn't go so badly for the Henry Ford Company after he left, either; it changed its name into one you might find a bit more recognizable: the Cadillac Automobile Company. Ford wasn't the only auto magnate who knew how bankruptcy felt, though. General Motors founder William Crapo Durant took a massive hit during the Great Depression that saw his fortune fall from $120 million to bankruptcy. He spent his last few years running a bowling alley in Flint, Michigan.
3. Walt Disney
His name may be a stalwart brand today, but early in his career, Disney was just a struggling filmmaker with too many bills. In 1922 he started his first film company with a partner in Kansas City, Kansas. The two men bought a used camera and made short advertising films and cartoons under the studio name Laugh-O-Gram. Disney even signed a deal with a New York company to distribute the films he was producing. That arrangement didn't work out so well, though, as the distributor cheated Disney's studio. Without the distributor's cash, Disney couldn't cover his overhead, and his studio went bankrupt in 1923. He then left Kansas City for Hollywood, and after a series of increasingly successful creations, Disney debuted a new character named Mickey Mouse in 1928.
4. Milton Hershey
Although he never had a formal education, Hershey spent four years apprenticing in a candy shop before striking out on his own in Philadelphia in 1876. Six years later, his shop went under, as did a subsequent attempt to peddle sweets in New York City. Hershey then returned home to Lancaster, Pennsylvania, where he pioneered the use of fresh milk in caramel productions and founded the successful Lancaster Caramel Company.
5. Burt Reynolds
Burt Reynolds was one of Hollywood's biggest stars of the 1970s. Unfortunately, though, he spent money like his career would never hit a downswing. He owned mansions on both coasts, a helicopter, and a lavish Florida ranch. Gradually, his financial situation got grimmer as he made boneheaded career choices and weathered a pricey divorce from Loni Anderson. By 1996, the Bandit owed $10 million to his creditors, Reynolds declared Chapter 11 bankruptcy, from which he emerged in 1998.