Kenny Chesney Gave Megan Moroney the Best Career Advice


Kenny Chesney took Megan Moroney out on the road his Sun Goes Down Tour in 2024, and Moroney told us that the 2025 Hall of Famer gave her a very down-to-earth piece of career advice.

Moroney was a guest on Taste of Country Nights, where host Evan Paul asked her what was the best advice Chesney gave her while she was on tour with him.

The “Am I Okay?” singer said, “I think he’s just embraced my authenticity, and he’s always encouraged that.”

Chesney told her that’s the key to her success, and to never change.

Moroney proves that she is authentically herself time and time again, whether it’s helping the cleaning crew clean up after a show, or pulling an epic prank on Chesney during the Sun Goes Down Tour.

Staying authentic is not the only thing Moroney learned from Chesney while touring with him.

“The biggest thing I’ve learned from him on tour is that good songs can make that country empire that he has,” she shared.

“He is in stadiums, so he could have the craziest production budget, he could have fire, he could be flying through the air, he could have like 10 stages out there that he goes and flies to. But he doesn’t; he literally just has his songs and him and a guitar.”

That Sun Goes Down Tour in the summer of 2024 was clearly a time that meant the world to Moroney.

In fact, she wrote a song about it titled “You Had to Be There,” which she gifted to Chesney. He sang on it with her, and they released the song to the public on May 9.

25 Best Kenny Chesney Songs That Prove He’s Country Music Hall of Fame Worthy

Kenny Chesney‘s best songs come from three distinct eras of his career. There are early career singles like “How Forever Feels” and mid-2000s hits like “When the Sun Goes Down,” “Summertime” and “Anything But Mine.”

What truly separates Chesney — a 2025 Country Music Hall of Fame inductee — from other artists is his third act. Six of the 25 songs on this list of Kenny Chesney’s best were released after 2010. It’s there he took some of his biggest risks, rewarding fans with some of the greatest lyrical moments and sounds of the 21st century.

We ranked the Top 25 Kenny Chesney songs using chart data, streaming and airplay numbers and staff/reader opinion. The year listed alongside the title is the year it was released as a radio single. The No. 1 song on this list exemplifies the best of what the Tennessee native is capable of.

Gallery Credit: Billy Dukes

PICTURES: See Inside Kenny Chesney’s Spectacular $11.5 Million Tennessee Estate

Kenny Chesney has sold his 4-bedroom, 9-bathroom, 12,599-square-foot hilltop estate in Tennessee for $11.5 million, and pictures show an opulent Mediterranean villa that is lavish even by the standards of other celebrity mansions.

Gallery Credit: Sterling Whitaker





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Graham Haring

Graham Haring is a versatile writer with a knack for capturing the heart of country music and the stories that surround it. Covering everything from new song releases by icons like Tim McGraw to unexpected cultural phenomena like "The Waffle House Index," his articles bring a mix of humor, depth, and curiosity to the table. Graham’s work often explores the personal side of country music, highlighting the community, family moments, and heartwarming stories behind the headlines. Whether it’s about Keith Urban's benefit shows or a quirky note from the past, Graham's writing resonates with country fans who appreciate a touch of authenticity and a good story.

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