Chris Stapleton, Jimmie Allen & More Record-Setters at 2021 CMA Awards

Luke Combs, Chris Stapleton and Jimmie Allen made history at the 55th annual CMA Awards on Wednesday (Nov. 10).

Combs won entertainer of the year, three years after winning new artist of the year. Combs is the seventh artist to make the steep climb from winning new artist of the year (formerly the horizon award) to entertainer of the year. He follows Ricky Skaggs (the 1982 horizon award winner), Garth Brooks (1990), Dixie Chicks (1998), Brad Paisley (2000), Keith Urban (2001) and Taylor Swift (2007).

Stapleton won four awards, more than anyone else for the night (and more than he has ever won in any one year). This brings his total of CMA awards to 14, which puts him in a tie with Miranda Lambert and Brad Paisley for the most wins by anyone in the 2000s.

Stapleton won album of the year for the third time for Starting Over. That’s the most wins in this category by any artist in this century. Since 2000, George Strait, Miranda Lambert and Eric Church have each won album of the year twice.

Going back over CMA history, which dates to 1967, Stapleton is one of only four artists to win album of the year three or more times (as lead artists). Strait is out front with five wins, followed by Ronnie Milsap with four. Johnny Cash is tied with Stapleton with three wins.

Stapleton also won both single of the year and song of the year for “Starting Over.” He won both awards three years ago for “Broken Halos.” He co-wrote both songs with Mike Henderson. They are just the second songwriting team to win song of the year for two different songs. Don Schlitz and Paul Overstreet won for co-writing Randy Travis’ hits “On the Other Hand” (the 1986 song of the year winner) and “Forever and Ever, Amen” (the 1987 winner). This are Stapleton’s 11th and 12th CMA Awards.

Stapleton took male vocalist of the year for a fifth time, which puts him in a four-way tie for the most wins in the history of the category. Blake Shelton, George Strait and Vince Gill have also won five times. Stapleton won every year from 2015-18, but lost the last two years to Luke Combs. This is the third time a male artist has regained the male vocalist of the year title after relinquishing it. Ronnie Milsap and Strait previously showed that resiliency.

Stapleton’s producer, Dave Cobb, and mix engineer Vince Powell, each won two awards.

Allen became the second person of color, following Darius Rucker in 2009, to win new artist of the year. Allen was nominated in this category last year, but lost to Morgan Wallen. (Artists are allowed to compete twice in the category.) Gabby Barrett and Ingrid Andress, also nominated in each of the last two years, will not be eligible to compete in the category again.

Carly Pearce won female vocalist of the year for the first time. This is the third year in a row that the award has gone to someone other than Miranda Lambert and Carrie Underwood, who dominated the category for many years. Kacey Musgraves won two years ago. Maren Morris won last year. Between them, Lambert and Underwood won the award in all but one year from 2006-18.

Brothers Osborne won vocal duo of the year for the fourth time. They won three years running from 2016-18, but lost the last two years to Dan + Shay. This is just the second time a duo has regained the vocal duo of the year title after relinquishing it. Brooks & Dunn won again after having their run interrupted by Montgomery Gentry in 2000.

Old Dominion took vocal group of the year for the fourth year in a row.

Kelsea Ballerini and Kenny Chesney ‘s “half of my hometown” won musical event of the year and music video of the year. These mark Ballerini’s first CMA wins and bring Chesney’s total of CMA wins to 11. This is the third time Chesney has won two awards in one night. He did the same in 2004 and 2007.

Fiddle player Jenee Fleenor, who two years ago became the first woman to win musician of the year, won in that category for the third year in a row. Steel guitar player Paul Franklin has now lost 29 times in the category, without ever winning. He has lost to Mac McAnally (10 times), Mark O’Connor (four times), Randy Scruggs and Fleenor (three times each), Johnny Gimble, Brent Mason, Dann Huff and Jerry Douglas (twice each) and Hargus “Pig” Robbins (once).

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