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On the business side of things, Chesney has become a very versatile musician which enabled him to appeal to a very wide audience of music fans. He then took that base and founded the Kenny Chesney corporation which expertly sells various items to his dedicated and loyal fans. Kenny Chesney is a singer-songwriter who has released twenty albums, nearly all of which have been gold-certified or higher by RIAA. This legendary star has had more than forty Top 10 singles on the country charts, twenty-nine of which has snagged the #1 slot. Chesney is a crossover artist whose style is among the most versatile in all of country music.
Net Worth: $500 million.
Venture: Show Dog Nashville.
Toby Keith went from a popular and highly successful singer to an absolute business magnate in just a span of 25 years. Keith managed to do in just two and a half decades what most successful entertainers and businesspeople never even accomplish in their lifetimes, and created a net worth that’s equal to half a billion dollars. The legendary singer-songwriter and actor was born in Oklahoma and has been a source of pride for them ever since.