Dierks Bentley Has Something to Say About Kenny Chesney's Career

Dierks Bentley spewed love when asked about Kenny Chesney's induction into the Country Music Hall of Fame, earlier this year, saying, "Nobody embraces their fanbase like he does."

Bentley was a guest on Taste of Country Nights, and we asked him to say some things about Chesney and how his career has affected him and country music as a whole.

The "What Was I Thinking" singer held back nothing when he went in on all the best things about Chesney.

"He's been such a great mentor to me, I love Kenny to death," Bentley says. "I'm so proud of him for being in the Hall of Fame, I know it means so much to him."

Bentley and Chesney have been friends for well over two decades now.

"This is the guy who has made country music, made the live show, made his fans his life's mission," he continues.

"They're his family. Nobody embraces his fanbase like he does."

Bentley went on to recall when he first got to tour with Chesney back in 2004, when he was the opener on Chesney's Guitars, Tiki Bars and a Whole Lotta Love Tour.

"I learned so much from being on the road with him," he says.

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"I went on that tour the first time thinking I knew what I was doing, because I was doing 300 shows a year. And I was like, 'I'm not gonna learn anything on this tour.'"

Boy, was he wrong!

Continues Bentley: "Oh man, I learned so much about how to treat your band, how to treat your crew and how to treat your fans. Nobody as deserving to be in the Hall of Fame than Kenny Chesney."

When Did Kenny Chesney Get Inducted Into The Country Music Hall of Fame?

On March 25, 2025, Kenny Chesney was revealed as a new inductee into the Country Music Hall of Fame, alongside June Carter Cash and producer Tony Brown.

The 2025 Country Music Hall of fame inductees will be formally enshrined in a Medallion Ceremony in October.

What Was Kenny Chesney's First Number One Song?

Chesney scored his first No. 1 hit in 1997 with "She's Got It All."

Since then, he has notched 30 more No. 1 hits.

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