Kenny Chesney Once Played a Show in Peyton Manning’s Apt. (Pics)

Kenny Chesney Once Played a Show in Peyton Manning’s Apt. (Pics)

Kenny Chesney was officially inducted into the Country Music Hall of Fame and Museum on Saturday (Oct. 19), and to celebrate, his longtime friend Peyton Manning shared a truly rare photo: Chesney performing a show in Manning’s college apartment.

A little backstory makes the moment even sweeter. Manning attended the University of Tennessee in Knoxville — Chesney’s hometown. When Chesney was still a rising star, he sang the National Anthem at a UT game and hung around on the sidelines afterward.

That’s where Manning, the team’s star quarterback at the time, struck up a conversation with Chesney. A friendship was born, and it’s lasted through decades of career milestones.

To honor Chesney’s Hall of Fame moment, Manning posted a throwback photo to Instagram that perfectly captures the early days of their storybook friendship.

Manning captioned the photo, “Congrats to my good friend Kenny Chesney on being inducted into the Country Music Hall of Fame. Long way from playing my college apartment party in 1998.”

At first glance, it’s hard to even recognize the “Beer in Mexico” singer. Chesney is wearing glasses and looks a little different from the ultra-fit country superstar fans know today — a true throwback to his early days on the rise.

Kenny Chesney Once Played a Show in Peyton Manning’s Apt. (Pics)

Apparently, the two became such good friends — in a time before texting and social media — that Manning could simply call up the rising musician and get him to play a show at his college apartment complex.

Little did those college kids know they were getting a private performance from a future Country Music Hall of Famer.

Manning and Chesney’s friendship only grew stronger over the years. Chesney even performed at Manning’s wedding, singing “Me and You” for the couple’s first dance.

“He performed “Me and You” for my wife and I for our first song at our wedding reception,” Manning told Luke Combs on his. “So just been good friends since then.”

The only real question now is — where did Manning even find that throwback picture? It’s nearly 27 years old and from the pre-digital era, making it an even more legendary snapshot of country music history.

Where Was Kenny Chesney Born?

Chesney was born in Knoxville, Tennessee, at St. Mary’s Medical Center and grew up in the nearby town of Luttrell.

What is Kenny Chesney’s Biggest Song?

Kenny Chesney’s biggest song is “The Good Stuff” due to the fact that it had a 7-week run at No. 1 and was named the No.1 country single of 2002. While this is somewhat of a subjective question, there is some proof behind the answer.

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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