The CMA Award for Entertainer of the Year is most coveted award in country music. Just 30 acts have won the award through the years—21 male artists, six female artists, two groups and one duo. Garth Brooks and Kenny Chesney are tied for the most wins in the category (four each, though Chesney would take the lead if he wins this year). Barbara Mandrell and Taylor Swift are tied for the most wins by a female artist (two each, though Swift would take the lead is she wins this year).
In 1981, Mandrell became the first artist to win twice. In 1984, Alabama became the first artist to win three times. In 1998, Brooks became the first artist to win four times. (He was also the first artist to regain the title after losing it. Until then, once an artist's winning streak ended, that was it.)
Eddy Arnold was the first winner when the awards were inaugurated in 1967. Arnold, who landed his first country hit in 1945, had the #1 album on Billboard's Top Country Albums chart for 20 weeks in 1967, more than any other artist. Arnold was 49 when he won, making him the oldest winner ever.
Taylor Swift is the youngest winner in the show's history. She was just 19 when she won for the first time in 2009.
In 1971, Charley Pride became the first African American winner. He is still the only one.
In 1982, Alabama became the first group to win. In 2000, Dixie Chicks became the second.
In 1996, Brooks & Dunn became the first duo to win. They are still the only one.
In 1999, Shania Twain became the first artist who was born outside of the U.S. to win. Twain was born in Canada. In 2005, Keith Urban became the second. Urban was born in New Zealand and raised in Australia.
Ricky Skaggs was the first Entertainer of the Year who had previously won the CMA's Horizon Award as the year's top newcomer. Garth Brooks, Dixie Chicks, Keith Urban, Brad Paisley and Taylor Swift subsequently took the same trip from the Horizon Award (now called New Artist of the Year) to Entertainer of the Year. Brooks made the trip the fastest. He won as Entertainer of the Year just one year after he won the Horizon Award. Dixie Chicks and Swift both took two years to make the journey. Skaggs took three. Urban took four. Paisley took a leisurely 10 years.
Winning is a highlight of most artist's careers. Several months after winning in 1972, Loretta Lynn released an album titled Entertainer Of The Year: Loretta, which topped the country chart in June 1973. Roy Clark, who won in 1973, released a double-disk compilation titled The Entertainer Of The Year in early 1974.
Several of the winners have had significant crossover success. Among them: Glen Campbell, John Denver, Shania Twain and Taylor Swift. Denver's selection in 1975 was controversial because many considered him a pop artist by that point.
Reba McEntire is the female artist with the most nominations (10). She's followed by Barbara Mandrell (six), Loretta Lynn (five) and Dolly Parton and Taylor Swift (three each).
Alabama is the group with the most nominations (five). They are followed by Oak Ridge Boys and Dixie Chicks (three each) and Rascal Flatts (two).
Brooks & Dunn is the duo with the most nominations (11). They are followed by The Judds (three) and Sugarland (one).
Here's a list of all artists who have received five or more Entertainer of the Year nominations. I also show how many times they won the award (and the years they won).
1. George Strait, 17 nominations, two wins (1989, 1990).
2. Alan Jackson, 12 nominations, three wins (1995, 2002-2003).
3. Brooks & Dunn, 11 nominations, one win (1996).
4. Reba McEntire, 10 nominations, one win (1986).
5. Merle Haggard, nine nominations, one win (1970).
Garth Brooks, nine nominations, four wins (1991-1992, 1997-1998).
Kenny Chesney, nine nominations, four wins (2004, 2006-2008).
8. Vince Gill, eight nominations, two wins (1993-1994).
Brad Paisley, eight nominations, one win (2010).
10. Keith Urban, seven nominations, one win (2005).
11. Charley Pride, six nominations, one win (1971).
Willie Nelson, six nominations, one win (1979).
Barbara Mandrell, six nominations, two wins (1980-1981).
Tim McGraw, six nominations, one win (2001).
15. Loretta Lynn, five nominations, one win (1972).
Ronnie Milsap, five nominations, one win (1977).
Kenny Rogers, five nominations, no wins.
Alabama, five nominations, three wins (1982-1984).