Loretta Lynn

Loretta Lynn became the first woman to win the Country Music Association's Entertainer of the Year award in 1972, breaking a 5-year male streak. Her song "The Pill" tackled contraception in 1975, reaching #5 on the country charts—a boldness that outpaces #8's Merle Haggard's political commentary by 7 years in terms of taboo subjects. With 16 number-one hits and over 15 million albums sold, she achieved 30% higher critical acclaim for her autobiographical songwriting than the average female country artist.