With the 2024 CMA Awards in our rearview mirror, we're looking ahead to next year's potential winners—and maybe even the next 25 years of winners!

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Let’s be real—predicting the next two decades of anything, especially a specific award, is basically impossible. But hey, we’re here to have fun, so why not?

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Before we get to who A.I. thinks will win the award, how does the CMA decide who the ‘Entertainer of the Year’ is?

The Country Music Association selects the 'Entertainer of the Year' based on a combination of talent, performance, and impact. This award honors an artist who excels in entertaining through concerts, media appearances, and overall fan connection.

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Industry voters consider factors such as tour success, charisma, and contributions to country music.

It’s not just about hit songs but also the artist’s ability to captivate audiences and elevate the genre—truly embodying the title of 'Entertainer of the Year.'

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We asked A.I. to take a crack at predicting the next 20 winners of the Country Music Association Awards’ Entertainer of the Year—and wow, it delivered.

To predict the next 25 years of CMA Entertainer of the Year winners, we developed a prompt that fed key factors into the A.I. for analysis. Starting with Morgan Wallen’s 2024 win, we asked the A.I. to project its selections based on data, including artists’ ages, career trajectories, historical trends, and the CMA’s overall impact and performance criteria.

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The A.I. used this information to project each year’s most likely winner, accounting for how artists age and the rise of younger talents over time.

By combining critical thinking with advanced technology, the A.I.’s predictions reflect both the dynamic trends of country music and the industry’s unpredictable nature.

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Keep scrolling to see which country artists the A.I. thinks will have some great years over the next two decades!

After reading who A.I. has selected to lead country music into the next era, come back and let us know what you think of the picks! We’d love to hear from you. Feel free to join the conversation by messaging us on the app.

A.I. Predicts the Next 25 CMA Entertainer of the Year Winners

Let’s be real—predicting the next two decades of anything, especially a specific award, is basically impossible. But hey, we’re here to have fun, so why not? We asked A.I. to take a crack at predicting the next 25 winners of the Country Music Association Awards’ Entertainer of the Year. And wow… it definitely delivered. Keep scrolling to see which country artists A.I. thinks will have some great years over the next two decades! 

2024 CMA Awards Red Carpet Pictures

Check out the best pictures from the 2024 CMA Awards red carpet.

Country couples and solo stars walked the red carpet ahead of the CMA Awards on Wednesday (Nov. 20). See pictures of the best and worst dressed stars, plus some of the wildest looks. There were certainly some bold hat decisions.

Gallery Credit: Billy Dukes

PICTURES: These 11 Country Stars Weren't at the 2024 CMA Awards

The 2024 CMA Awards took place in Nashville on Wednesday night (Nov. 20), and country music's biggest stars were all on hand ... with a few very notable exceptions.

Gallery Credit: Sterling Whitaker

These Country Artists Are Touring in Maine in 2025

Maine sure loves its country music, and it’s easy to see that country artists feel the same way about us! This mutual love means that in 2025, Maine will be hosting a fantastic lineup of country stars who can’t wait to perform here. Check out this list of artists already scheduled to bring their music to our Pine Tree State in 2025!

Gallery Credit: Jordan Verge

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