Big Kenny Alphin of Big and Rich might have the country record for most careers held before achieving success on Nashville's biggest stages. According to a 2005 article at Co-Opliving.com, the blond half of the duo held several jobs and ran several businesses before finishing high school. There was the T-shirt company, then he ran a logging crew...  

By age 25 he'd made and lost a fortune building houses as a real estate developer, until a recession led to his company spiraling into bankruptcy. This was five years before he first tried Nashville in 1994 -- at the age of 30. He and John Rich wouldn't score their first hit until 'Wild West Show' in 2003. 'Save a Horse (Ride a Cowboy)' peaked at No. 11 one year later.