Expert Predictions: The 58th Annual CMA Awards—Who Will Win vs. Who Should Win

Luke Bryan, Lainey Wilson, and Peyton Manning will host “The 58th Annual CMA Awards” on Wednesday. And while we won’t know who wins until the show airs live from Nashville’s Bridgestone Arena at (8  – 11 PM/ET) on ABC, we can have some fun predicting the outcome.

Who do you think will emerge as the night’s biggest winners? Here are our guesses:

Videos by American Songwriter

Entertainer of the Year:

Will win: Jelly Roll

Typically, artists from the largest label groups do well at the CMA Awards. But last year, when Lainey Wilson won Entertainer of the Year, Broken Bow Label Group/BNA proved they also knew how to move the needle. Jelly Roll has had a genre-defying yet country-music-centric year. He’s the comeback kid everyone is rooting for. His devotion to his family, his fans, the underdog, community service – and creating meaningful art and crafting speeches with unforgettable messages is unparalleled at the moment. He’s reaching across genre lines to bring more people in every time he publicly speaks. Reaching people and growing the genre is what Entertainer of the Year is all about.

Should win: Morgan Wallen

Wallen released his third studio album, One Thing At A Time, in 2023, and it stayed at the top of the all-genre Billboard 200 chart for 19 non-consecutive weeks, the record at No. 1 for a country album.
The album’s seven-times platinum single “Last Night” earned more than 2.2 billion streams globally and is the longest-running No. 1 solo song in Hot 100 history. His recent collaboration with Post Malone, “I Had Some Help,” debuted on country radio with 167 first-week ads, only the second single in chart history to debut with the support of all reporting stations.

His 87-show One Night At A Time World Tour stretched two years, 10 countries on three continents, and includes 51 stadium gigs for more than 3.1 million fans.

Album of the Year:

Will win: Chris Stapleton, Higher

When nominated, Chris Stapleton has only lost this category once. In 2018, Kacey Musgraves’ Golden Hour bested his From A Room: Volume 2. Now, the two are headed for a rematch on Wednesday night as her Deeper Well is pitted against his Higher. Will she win again? It’s hard to predict because Musgraves and Deeper Well were not intensely focused on country music this album cycle. Her songwriting and artistry are infallible, but voters are often creatures of habit. Higher is a work of art delivered by the most respected and celebrated voice of this generation in country music.

Should win: Jelly Roll, Whitsitt Chapel, OR Morgan Wallen (but he isn’t nominated)

Whitsitt Chapel is the album that propelled Jelly Roll from country newcomer to one of the genre’s main spokespeople. His unforgettable performance of “Need a Favor” at the 2023 CMT Awards hitched him to a rocket that has yet to slow down.  

Female Vocalist of the Year:

Will win: Lainey Wilson

Wilson is the reigning Entertainer of the Year, is among the most beloved artists in the format, and has scored seven No. 1 hits, including “Watermelon Moonshine.” She made her acting debut in season 5 of Yellowstone and will return to the series this year for its final season. She was inducted into The Grand Ole Opry by Garth Brooks and Trisha Yearwood earlier this year and recently wrote and recorded “Out of Oklahoma” for Universal’s blockbuster Twisters.

Should win: Kelsea Ballerini

Kelsea Ballerini just released her new studio album Patterns, headlined Madison Square Garden, and announced her 36-date KELSEA BALLERINI LIVE ON TOUR that launches in January 2025.
In addition, the East Tennessee native is the face of COVERGIRL and Pantene. She will serve as Coach on Season 27 of NBC’s The Voice, premiering in Spring 2025.

Male Vocalist of the Year:

Will win: Chris Stapleton

Chris Stapleton has won every year since 2021. And with the exception of 2019 and 2020, when Luke Combs took the trophy, Stapleton has annually captured the category since 2015 – the year he released Traveller, his debut album.

Should win: Cody Johnson

I’m never going to say Stapleton SHOULDN’T win Male Vocalist of the Year, but have you all heard Cody Johnson? He has a bulletproof voice, and the man is on a tear. He’s got two songs in Song of the Year, two videos in Video of the Year, his album Leather is up for Album of the Year, and if Johnson never wins Entertainer of the Year, it will be one of country music’s most significant oversights.

Vocal Group of the Year:

Will win: Old Dominion

Old Dominion just released their album Odies But Goodies and is still the most visible band in the genre — on stage and radio. They’ve won this category since 2018.

Should win: Red Clay Strays

Both bands are signed to Sony, which means they could cancel each other out and make way for Little Big Town on UMG to slide in and take the category. However, Red Clay Strays is the most talked about new band in country music. The group just headlined multiple nights at Ryman Auditorium. They haven’t made a huge splash on country radio yet, but people love their edgy, throwback style.

Duo of the Year:

Will win: Brothers Osborne

Brothers Osborne has won this category for six of the last eight years, regardless of radio airplay. They are immensely likable, record hard-rocking country-esque songs, and stand for inclusion and diversity. They are also signed to UMG.

Should win: Dan + Shay

Dan + Shay, who bounced back from a near breakup in 2021, released their album Bigger Houses a couple of years later and dropped singles “Save Me the Trouble,” “Bigger Houses,” and “Heartbreak on the Map.” A few weeks ago, the men released their highly anticipated Christmas double album, It’s Officially Christmas: The Double Album.

New Artist of the Year:

Will win: Megan Moroney

Moroney is, without a doubt, country music’s new-it girl. She just spent the summer on tour with Kenny Chesney playing stadiums. She released her critically acclaimed sophomore album Am I Okay? in July 2024, and it debuted at No. 9 on the Billboard 200. It emerged as the year’s third-biggest debut from a female Country artist.

Should win: Shaboozey

Shaboozey is a current six-time Grammy nominee whose “A Bar Song (Tipsy)” is the biggest consumed track of 2024. “A Bar Song (Tipsy)” has the record for the longest-leading Hot 100 No. 1 track by a solo artist (17 weeks). The song also topped the Billboard’s Hot Country Songs, Country Airplay Chart, and Mediabase/Country Aircheck charts. Shaboozey made history as the first artist to have a No. 1 song across all four charts: Country Airplay, Pop Airplay, Adult Pop Airplay, and Rhythmic Airplay.  He’s the first Black male artist to top both the Billboard Hot 100 and Country Songs Charts. The song has amassed over one billion streams and landed in the Top 10 in several countries, with multiple No. 1s.

Single of the Year:

Will win: Post Malone/Morgan Wallen “I Had Some Help”

The Malone/Wallen collab “I Had Some Help” debuted on country radio with 167 first-week ads to make it only the second single in chart history to debut on all country reporting stations. “I Had Some Help” stayed at No. 1 on the Billboard Hot 100 all-genre charts for six weeks.

Should Win: Shaboozey, “A Bar Song (Tipsy)”

As previously stated, “A Bar Song (Tipsy)” is the most consumed track of 2024. “A Bar Song (Tipsy)” has the record for the longest-leading Hot 100 No. 1 track by a solo artist (17 weeks). However, Shaboozey hasn’t spent much time in Nashville, and I’m unsure if voters will cast their ballot for someone they might view as a temporary in the genre.

Song of the Year (the award goes to the songwriters):

Will win: “White Horse” (Chris Stapleton, Dan Wilson) or “Burn It Down” (Hillary Lindsey, Parker McCollum, Lori McKenna, Liz Rose)

It is rare that Chris Stapleton loses a Song of the Year nomination. His songs are beloved and respected – in addition, he’s represented by some of the heaviest voters in town. However, this year, he’s up against the Love Junkies who wrote “Burn It Down.” Both Stapleton and Parker McCollum are on the same label, and the Love Junkies are among the most revered songwriters in country music.
Anything could happen.

Should win: “Dirt Cheap” (Josh Phillips)

This is a hard category for a Cody Johnson song to win because two songs by him are in this category – and both are spectacular. However, “Dirt Cheap” is a one-writer song that almost never happens these days, and it is a fresh look at what’s important in life.

Musical Event of the Year:

Will win: “I Had Some Help”

Should win: “I Had Some Help”

Music Video of the Year:

Will win: Megan Moroney, “I’m Not Pretty”

Moroney’s “I’m Not Pretty” is what every young woman wants to think when suffering a broken heart. Moroney is all about branding, vision, songwriting, and storytelling in a new and fresh way that speaks to the young and the young at heart.

Should win: Lainey Wilson, “Wild Flowers and Wild Horses”

The video is a beautiful cinematic storytelling that showcases Wilson’s horsemanship, acting skills, and intensity as an artist. It leans into Yellowstone vibes and showcases her authenticity and artistic point of view.

(Photo by Taylor Hill/WireImage)

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