John Harvey Kellogg First Career

Harry Truman, haberdasher:
The president who dropped the A-bomb had much more humble beginnings. He was a bank clerk and bookkeeper, served in the National Guard and in WWI, and after the war, opened his own men's haberdashery store in Kansas City, MO, with a friend.

Graham Chapman, doctor:
Before Monty Python success, Chapman wrote for the BBC and worked on radio and TV series, with John Cleese and other future collaborators. But even before the entertainment business, the British actor and writer studied at the Barts and The London School of Medicine and Dentistry. He met Cleese at this time, and together, the two wrote sketches together. While some sources say that Chapman did not practice medicine professionally, others say that he was a doctor for a few years before turning to show business full time.

Grover Cleveland, sheriff and executioner:
Twenty-second President of the United States Grover Cleveland was the first Democrat elected after the Civil War, but his early days in politics were less demonstrative. After losing the race for New York's Erie County DA, he was elected sheriff for the area, and even carried out hangings personally, to save himself the $10 executioner fee.