11:Larry King

Source: Today.com

When Larry King started working on the radio in 1960, his low salary job was not enough to fulfill his lavish lifestyle. His woes were about to increase when he was sued by a business partner for stealing $5000 and was fired from his job. He remained out of job for 4 months which only made things worse. By 1978, he had to file for bankruptcy after accumulating more than $350,000 in mortgage loans and debts.

Luckily for him, the same year he declared bankruptcy, Larry King was hired to host a national night-time talk show. One thing led to another and King ended up running the show for 25 straight years. He is known to have interviewed most prominent personalities of his time including big Hollywood stars, Politicians, Businessmen and athletes.