The 20 biggest CMT Music Award winners of all time

Country music legend and former “Hee Haw” host Roy Clark won his first CMT Music Award back in 1969, when the event was still called the Music City News Awards. The honor was for Instrumentalist of the Year, a category that has since been retired. He won that category (or Instrumentalist Entertainer of the year, which was added in 1974) eight times. Additionally, he was presented with a Minnie Pearl Humanitarian Award in 1999, which brought his grand total of wins to nine. Roy Clark also hosted the event in 1985 and 1991!

Not to be confused with the much younger country act known as the Brothers Osborne, the Osborne Brothers started performing together back in the 1950s and soon became one of the most popular bluegrass bands of all time. Hence their nine wins for Bluegrass Group of the Year. Best known for their 1967 hit “Rocky Top,” Sonny and Bobby Osborne would stay a performing pair until 2003, when the former retired. Bobby, however, is still playing today!

The Buckaroos won Band of the Year at the Music City News Awards a total of five times - including the first four events in a row! Even after the group split in the mid ‘70s, band leader Buck Owens kept right on playing, and ended up adding four more awards to his collection: Instrumentalist of the Year in both 1974 and 1975, a 1980 Founder’s Award, and Video Collaboration of the Year in 1989 for “Streets of Bakersfield” with Dwight Yoakam.

If you haven’t noticed, we’re in the midst of a pretty massive tie amongst artists with nine wins, and Ricky Skaggs is no exception. The legendary mandolin, guitar, fiddle, and banjo player won his first award, Bluegrass Group of the Year, back in 1982, and then won the same honor again in 1983 (as well as a Star of Tomorrow in the same year) and 1984. After that, he moved to the Instrumentalist of the Year category, which he won in 1987, 1988, 1989, and 1990. In 1996, he won his final award, Video Collaboration of the Year, for his part in Vince Gill’s “Go Rest High on That Mountain” along with Patty Loveless and Vince Gill himself. Nine wins might seem like a lot for anyone, but remember that Chet Atkins once said Skaggs "single-handedly" saved country music.

The Judds, the mother and daughter team of Naomi and Wynonna Judd, are one of the most successful duos in country music history. They’re also one of the most successful duos in CMT Music Awards history, as they’ve taken home a total of nine honors. After winning a Star of Tomorrow award at the 1985 Music City News Awards, the remaining eight trophies were all  for either Duet of the Year or Vocal Duo of the Year, with the most recent in 1992. In case we lost you with all that math, that means the Judds won at least one award in eight straight years.

Ray Stevens is as much a comedian as he is a musician, so it’s no surprise that he’s won some CMT/Music City News Awards for Comedian of the Year. What is a bit surprising, however, is that he won a total of nine straight honors in this category between 1986 and 1994. The man who finally dethroned Stevens? That would be Mr. Jeff Foxworthy.

Although Randy Travis recorded his first album back in 1978, he didn’t win a Music City News Award until almost a decade later. Looking to make up for lost time, Travis would go on to earn nine honors in three years, including four each in 1987 and 1988. Although he never won again after that, Travis hosted the event alongside George Jones and LeAnn Rimes in 1997.

Vince Gill sure made the rounds with his nine wins. He started with two victories for Instrumentalist and Single of the Year in 1991, and would later add wins in both these categories yet again, as well as Album of the Year, Vocal Collaboration of the Year, the Minnie Pearl Award, and a Career Achievement Award in 2001. By the time he was through, the Music City News Awards was renamed the TNN & CMT Country Weekly Music Awards. Gill can break out of this massive tie in 2017, as he’s nominated in the Collaborative Video of the Year category for his duet, “Sober Saturday Night,” with Chris Young.

One of just three duos in this list, Brooks & Dunn ruled the Vocal Duo of the Year category for seven consecutive years between 1993 and 1999. They returned again to claim the honor in 2002, when it was renamed “Duo Video of the Year,” and a final time in 2010. They split on good terms to pursue solo careers after that, but Brooks & Dunn reunited in 2015 and are still performing together, so hopefully another record (and CMT Award) is in their not-too-distant future.

Tim McGraw also finds himself locked into this 10-way tie amongst artists with nine wins, but he has not one, but two chances to break out of it this year. For the 2017 CMT Music Awards, McGraw is nominated for both Duo Video of the Year (“Lovin’ Lately” with Big & Rich) and Collaborative Video of the Year (“May We All” with Florida Georgia Line). He won his first award for Male Star of Tomorrow in 1995, and most recently won just last year for Video of the Year.

Dolly Parton won twice at the second-ever Music City News Awards event in 1968 for Most Promising Female Artist and Duet of the Year, with the latter shared between her and Porter Wagoner. That duo would earn the same honor again twice over the next two years, and Dolly would add seven more awards after that, with her most recent in 2006. Since then, she has released four more albums, but hasn’t been able to add to her collection of 11 trophies.

For someone who is still only 44 years old, Brad Paisley has a surprising 12 CMT Awards. After earning his first in 2000, Paisley went on a tear, twice winning three honors in a single year. His victories have also been quite diverse, as he has fended off the competition in categories from Male Video of the Year to Comedy Video of the Year (for the 2007 tune “Online”). Brad’s most recent win was for his “Remind Me” duet with Carrie Underwood back in 2012, but he can add another in 2017 if “Today” manages to win Video of the Year.

Reba McEntire won her first Music City News Award back in 1985, and over the next two decades she added a dozen more - including nine wins for Female Artist of the Year. She ain’t done yet though, as Reba has a shot at adding another honor at the 2017 CMT Music Awards. Her song “Back to God” (off of her 29th and latest album, “Sing It Now: Songs of Faith & Hope”) received a nod for Female Video of the Year - proving that Reba is still relevant after all these years.

 Ricky Van Shelton was only active as a country musician for two decades (from 1986 to 2006), but during that time he recorded nine studio albums, 10 No. 1 hits, 17 top-10 singles, and earned a whopping 14 Music City News Awards. This included everything from Star of Tomorrow to Entertainer, Male Artist, and Christian Country Artist of the Year, as well as honors for Single, Album, and Video of the Year. Two of these awards were also shared with Dolly Parton, as the duo recorded “Rockin’ Years” together in 1991.

Oh, and in case you were wondering, Ricky Van Shelton is in no way related to Blake Shelton.

George Strait burst on the Music City News Awards scene in a big way, winning the coveted category of Male Artist of the Year in 1986. He went on to win it once more, as well as two trophies for Entertainer of the Year...and then an additional 11 honors. Strait’s last award came in 2009, when he, Alan Jackson, Brad Paisley, and Dierks Bentley won Performance of the Year for their rendition of Jackson’s “Country Boy.”

If we want to get technical, Carrie Underwood has won the most CMT Music Awards of all-time. That’s because she owns a total of 17, all of which have been earned since CMT became associated with the award show back in 2001. Getting technical again, all 17 have actually been won since 2003, which shows that the singer/songwriter has been plenty busy. In fact, out of the eight years in which Underwood earned an award, only two were one-win years.

 Conway Twitty only spent 59 years on this Earth, but he certainly made the most of his time. Twitty released an unfathomable 57 studio albums during this time (which excludes compilations) and won 18 Music City News Awards between 1970 (a Song of the Year win for “Hello Darlin”) and 1988 (a Living Legend honor). Of his 18 awards, he shared 10 with Loretta Lynn for Duet of the Year.

The winningest woman in CMT Music Awards history is Ms. Loretta Lynn, who is still kicking today at 85 years of age. As we previously mentioned, 10 of Loretta’s awards were for duets with Conway Twitty, but other than a 1974 win for Touring Road Show of the Year, the rest were all her. She won at least one honor in each of the event’s first 12 years, with as many as three in one show. Loretta’s latest was a Johnny Cash Visionary Award in 2005.

As far as solo artists go, no one has been more successful at the CMT Music Awards than Alan Jackson. All but two of his 29 wins have all come between 1991 and 2002, which goes to show how incredibly popular Jackson was during his prime. (The other two wins were Performance of the Year in 2009 and a CMT Impact Award in 2014.) In fact, Jackson won five honors in a single night — twice — in back-to-back years!

We know what you’re thinking, and no, that’s not a typo. The Statler Brothers actually won 46 times throughout the history of the Music City News/CMT Music Awards. The quartet (of which only two members were brothers, and no one had the surname Statler) first won at the fifth installment of the event in 1971, and then earned at least one honor at every show for the next 23 years. Vocal Group of the Year was The Statler Brothers’ category of choice, but their victories weren’t limited to just one slot. In fact, they once earned six awards in a single night (in 1985, when they also co-hosted the event), as well as 15 wins in just three years. Not bad for a band who got their start playing backup for Johnny Cash.