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Swindell has released nine singles so far with seven of them making it to number-five or higher on the country charts. He has over a million likes on Facebook and managed to become a multi-millionaire in his mid-thirties. In 2015, Swindell won the Best New Artist of the Year by the Academy of Country Music Awards. His most successful singles so far have been “You Should Be Here,” “Middle of a Memory,” “Break Up in the End,” and our favorite, “Chillin’ It.”
Net Worth: $26 million.
Venture: Bret Maverick.
Ed Bruce is best known as everyone’s favorite original outlaw country singer and avid traditionalist of the genre. Born in Keiser, Arkansas, the talented young Bruce quickly caught the attention of Sam Phillips, the founder of Sun Records, and began writing and recording various songs for him. Bruce then proceeded to do voice-overs for TV shows and radio commercials, and finally debuted his first single in 1969 to moderate success. The aspiring singer finally made big progress when he released “Mamas Don’t Let Your Babies Grow Up to Be Cowboys”, a song which he wrote with his wife. The song reached the Top 20 charts and his career began improving quickly from there.