2020: Lambert and Underwood are both nominated. This is Lambert’s fourth nomination in this category; Underwood’s third. Neither has yet won.
2010: Lambert and Lady A (as the mixed-gender trio is now known) were both nominated. Brad Paisley won. This was Lambert’s first nomination in this category; the only one for Lady A, which features Hillary Scott.
2000: Faith Hill and The Chicks (as the female trio is now known) were both nominated. The Chicks, consisting of Natalie Maines and sisters Martie Erwin Maguire and Emily Strayer, won. This was Hill’s only nomination in this category; The Chicks’ second of three in a row.
1999: Shania Twain and The Chicks were both nominated. Twain won. This was Twain’s only nomination in this category; The Chicks’ first.
1986, 1987, 1988: Reba McEntire and The Judds were both nominated three years running -- the longest continuous stretch where more than one woman was nominated. McEntire won in 1986. Hank Williams Jr. won the next two years. The Judds consisted of mother Naomi and daughter Wynonna. McEntire was first nominated in this category in 1985. She was nominated in 10 out of 11 years from 1985-95. (She missed the cut in 1990, when Kathy Mattea was the sole female nominee.) These were The Judds’ only three nominations in this category.
1979: Gayle and Mandrell were both nominated. Willie Nelson won. This was Gayle’s second nomination in a row in this category; Mandrell’s first of six in a row. Mandrell is the only woman in CMA history to be nominated in this category six years in a row. (As noted above, McEntire could have been nominated 11 years running, but her streak was interrupted at its midpoint.)
1978: Gayle and Dolly Parton were both nominated. Parton won. This was Parton’s third consecutive nomination in this category; Gayle’s first. Inexplicably, Parton hasn’t been nominated for entertainer of the year since winning in 1978. (I ask you: Who has been more entertaining over the past 42 years?!)
1974: Loretta Lynn and Olivia Newton-John were both nominated. Charlie Rich won. This was Lynn’s fourth of five consecutive nominations in this category, Newton-John’s only one. (Many may not even remember that Newton-John was a country/pop crossover star in the mid-‘70s. After the success of Grease in 1978, she pivoted to a pure pop style. Decades later, Taylor Swift would make a similar musical transformation.)