18. Lefty Frizzell
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The charismatic Frizzell could make even the saddest of ballads seem optimistic with his bouncy vocals. Many pundits credit Frizzell for greatly helping country music achieve mainstream popularity. He made music that was easily digestible and less coarse than the typical honky tonk sound that had come before him. Frizzell’s reach extends to some of the genre’s all-time greats – including Willie Nelson, Keith Whitley, and George Jones. To this day, Frizzell remains the only country artist to have four songs reach the No. 1 spot on Billboard’s country music charts in the same calendar year.