Billboard Women in Music of "her success as a recording artist, contributions to the business, and leadership in embracing the changing music business." Every year since then, "Billboard" has honored a female artist with the award. Taylor Swift is the only woman to be honored twice. The most recent winner of this award is Ariana Grande. In 2008, Colbie Caillat was honored with "Billboard"'s first Rising Star award because of "her ascent in the pop charts and the repercussion that her music caused." Every year since then, "Billboard" has honored a female artist with the award. In 2010, Lea Michele was honored with "Billboard"'s
Entertainer of the Year Billboard (North America) Singles – Billboard (North America) Entertainer of the Year Entertainer of the Year is the twenty-first studio album by American country music singer-songwriter Loretta Lynn. It was released on February 26, 1973, by MCA Records. This was Lynn's first album with MCA following Decca's consolidation into the MCA label. This album was titled after Lynn received the "Entertainer of the Year" award from the Country Music Association the previous year, becoming the first woman to win that award. The album peaked at No. 1 on the "Billboard" Top Country Albums chart, becoming her fourth album to top