7 Massive Country Stars Who’ve Never Won CMA Entertainer Of The Year

Toby Keith Carrie Underwood Jason Aldean

Some major snubs here.

With the 60th annual CMA Awards airing live from the Bridgestone Arena in Nashville in just over a month on Wednesday, November 18th, the buzz surrounding the show keeps growing with each passing day. With Ella Langley, Miranda Lambert and Kacey Musgraves leading the way with the most nominations across the 12 major categories, Chris Stapleton, Cody Johnson and Stephen Wilson Jr. are also among the night’s top-nominated artists.

Following the trend set by the past two CMA Awards, women absolutely dominate this year’s set of nominees. To absolutely no one’s surprise, Ella Langley is riding the highs of her record-shattering success with “Choosin’ Texas” to a staggering nine nominations. These nominations include her first-ever Entertainer of the Year nod, Album of the Year for Dandelion, Single and Song of the Year for both “Be Her” and “Choosin’ Texas,” Female Vocalist of the Year, Music Event of the Year (“I Can’t Love You Anymore” with Morgan Wallen) and Music Video of the Year (“Choosin’ Texas”).

Right behind her with seven is “Choosin’ Texas” co-writer and superstar, Miranda Lambert, who snagged seven nominations. These include her work on both Langley’s Dandelion and “Choosin’ Texas” as well as Female Vocalist of the Year, and two Musical Event of the Year nods for “A Song to Sing” with Chris Stapleton and “Horses and Divorces” with Kacey Musgraves.

Leading the charge for the men are the likes of Chris Stapleton, Cody Johnson and Stephen Wilson Jr with four nominations. In particular, Wilson Jr. is primed to have a huge night. As a fan-favorite amongst many alt. country fans and us here at Whiskey Riff, the “I’m a Song” singer snagged four nods, including his first-ever Male Vocalist of the Year mention, New Artist of the Year and Song and Music Video of the Year for “Gary.”

Finally, Entertainer of the Year will see Langley, Johnson and Stapleton compete against Luke Combs and Lainey Wilson for the night’s biggest honor.

And as the anticipation for this year’s awards continues to grow in the days leading up to the show, there’s bound to be a ton of discussions around which artists deserve to win each award, who continues to get robbed and everything in between. And that’s what we’ve been doing here at Whiskey Riff lately.

Over the past few days, we’ve taken a look at some major snubs throughout the years, ranging from artists who shockingly never took home a single CMA Award throughout incredibly successful years to other artists who have brought home major wins without winning Male Vocalist of the Year.

Today, we’re looking at seven of the biggest artists in the genre’s history who have failed to win the show’s biggest award — Entertainer of the Year.

Randy Travis

Few living artists have made an impact on country music the way Randy Travis has. With over 23 million albums sold worldwide, 23 #1 singles, seven Grammys and dozens upon dozens of awards from the likes of the ACMs and CMAs, the “I Told You So” singer has paved the way for over two generations of artists at this point.

Though he’s collected five CMAs throughout his career, including two Male Vocalists, as well as Single and Album of the Year for “Forever and Ever, Amen” and Storms of Life, Travis has never won a single Entertainer of the Year. Being nominated for four straight years from 1987 to 1990, he dropped it twice to both George Strait and Garth Brooks.

Nominated – 4

  • 1987
  • 1988
  • 1989
  • 1990

Carrie Underwood

At this point in her career, Carrie Underwood has already hit legend status in the genre. Along with her 12 ACM Awards (including 3 Entertainer of the Years), eight Grammy Awards, seven CMA Awards and a plethora of other hardware from Billboard, Dove and more, last year, she became the highest-selling female country artist of all time, according to the Recording Industry Association of America (RIAA).

What’s shocking, however, is the fact that she never once won or was even nominated for EOTY at the CMAs during the height of her career. Looking back, her history of nominations is truly baffling. Despite Underwood’s most successful years being roughly from 2005 to 2015, she did not receive a single nomination during that stretch. Instead, she somehow received her first nod in 2016 before inexplicably getting nominated for five straight years from 2019 to 2023, even though her most successful years commercially were behind her.

Nominated – 6

  • 2016
  • 2019
  • 2020
  • 2021
  • 2022
  • 2023

Chris Stapleton

It’s hard to understate just how much of a force to be reckoned with Chris Stapleton has become throughout his music career. With 11 Grammys, 19 CMA Awards, 11 ACM Awards and a plethora of other hardware from the likes of Billboard, the Americana Music Association, ASCAP and more, the Kentucky native is arguably the biggest and most critically-acclaimed country artist this century. Among all the awards, last week, Stapleton made history as the only artist to capture a double-diamond song from the Recording Industry Association of America (RIAA) as his cover of David Allan Coe’s “Tennessee Whiskey” officially sold over 20 million units in the U.S.

Of course, there’s so much to talk about when discussing Stapleton’s career as a whole. From his iconic breakout during the 2015 CMA Awards that signaled the death of bro-country, to his laundry list of hits, to his long history as a songwriter in Nashville before his fame as a solo artist, the Chris Stapleton lore runs incredibly deep.

What’s truly fascinating about Stapleton, as far as the CMA Awards are concerned, is the number of trophies he’s racked up without taking home Entertainer of the Year. Despite being the second-most-decorated artist in the history of the award show with 19, one behind Brooks & Dunn, the “Broken Halos” singer has gone home empty-handed in the EOTY category a staggering 10 straight years.

This year, Stapleton is looking to snap his ten-year losing streak as he is nominated again.

Years Nominated – 11

  • 2016
  • 2017
  • 2018
  • 2019
  • 2020
  • 2021
  • 2022
  • 2023
  • 2024
  • 2025
  • 2026

Toby Keith

There’s no doubt that the late, great Toby Keith was one of the most popular country artists for the better part of two decades in the ’90s and early 2000s. From a legacy standpoint, few artists have matched the “Should’ve Been a Cowboy” singer’s career accomplishments. Beyond his recently-named status as one of the top touring artists of the millennium (#24 overall), Keith scored 41 Top 10 hits, 20 #1 singles, 10 #1 albums, 14 ACM Awards and a plethora of other awards throughout his illustrious career.

Despite so much success for nearly three decades, he rarely got shown much love from the CMAs. In fact, he only scored three wins throughout his career, grabbing Male Vocalist of the Year in 2001 and two Music Video of the Year awards for “As Good As I Once Was” and “Red Solo Cup.”

During the peak of his popularity after the resounding success of his post-9/11 anthem, “Courtesy of the Red, White and Blue (The Angry American),” as well as other tracks like “American Solider,” “Beer for My Horses” and “As Good As I Once Was,” Keith would score four straight nominations for Entertainer of the Year from 2002 to 2005. Despite this, he’d come home empty-handed each time.

Years Nominated – 4

  • 2002
  • 2003
  • 2004
  • 2005

Zach Bryan

It’s hard to imagine a more fascinating artist in today’s country music landscape than Zach Bryan. In a six-year span, the “Something in the Orange” singer has gone from recording his debut album, DeAnn, in a Florida Airbnb and scoring viral hits online to selling his publishing catalog for a staggering $350 million and, most notably, setting the record for highest-attended concert in U.S. history when he performed to a crowd of 112,408 at Michigan Stadium.

Though there’s no doubt that artists such as Tyler Childers, Sturgill Simpson and Cody Jinks were the forefathers of the current independent and alternative country renaissance we’ve currently been experiencing over the better half of a decade, there’s no denying that Bryan was the one who blew the door off the hinges, so to speak.

Despite being so popular and cemented in the mainstream as far as all-genre artists are concerned, Bryan has never won a single CMA Award — let alone received an Entertainer of the Year nod. And while that might seem surprising to casual fans, it makes a lot of sense considering the Oklahoma native himself publicly stated he never wants to be considered at the show back in 2022.

“Guys, I don’t and will never want to be considered at the CMAs. My pride is fine and I appreciate all the love and support and I say it with every ounce of respect to other country artists

To be clear, I’m not trying to insult the validity of a CMA, I respect any artist who receives one and the existence of them; I’m just saying on a personal level it is not one of my priorities to have awards on a shelf in my home. There’s room for more important things there.

I think there are so many talented artist that deserve awarded and will be awarded, and some just don’t care enough about a silly TV program to need an award in the first place.”

Years Nominated – 0

Jason Aldean

Reigning ACM Artist of the Decade, Jason Aldean, has had a pretty fascinating career. With 32 #1s, 27 platinum certifications from the Recording Industry Association of America (RIAA), and over 55 million units sold in the U.S. alone, the “She’s Country” singer has had a career few could ever dream of — just not at the CMA Awards.

Similar to Underwood, Aldean is another artist who is inexplicably loved by the ACMs but shown little to no affection from the CMA Awards. Like the “Before He Cheats” singer, Aldean also has three-straight ACM Entertainer of the Year awards, winning three straight from 2016 to 2018. Over at the CMAs, however, he only has four nominations overall — losing each one.

Years Nominated – 4

  • 2011
  • 2012
  • 2013
  • 2018

Florida Georgia Line

Hear me out, I’m not upset about Florida Georgia Line never winning Entertainer of the Year in any way, shape or form. With that being said, however, it’s a bit surprising, looking back, that they have never been nominated for, let alone won an EOTY during the height of their popularity in the 2010s.

It should go without saying at this point that FGL was once one of the most successful duos in the history of the genre, scoring nothing short of era-defining hits in the 2010s with the likes of the diamond-certified “Cruise,” along with other smashes such as “This Is How We Roll,” “Stay” and the Bebe Rexha collaboration, “Meant to Be.” Simply put, the crossover popularity they experienced during the height of their career is rivaled by few in the genre.

In a similar vein to discussions around Morgan Wallen, you can truly despise their music, but if you look at their success from an objective lens, it’s quite shocking that they were never put in consideration for the genre’s biggest award, especially considering their popularity.

Years Nominated – 0

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