From Then to Now: The Growth of Dierks Bentley Across 20 Years of Country Music

Dierks Bentley is one of the country artists who's built a thriving career by continuously evolving without losing himself along the way. For two decades, his creativity, sound, and even hairstyle have shifted while keeping that unmistakable Bentley charm fully intact. His recent musical direction further proves he’s still the same guy who barged in the doors of Nashville all those years ago.

Today we're diving into how Bentley’s newest releases show respect for his country roots, and how he continues to grow as an artist without losing the elements that made fans fall in love with him in the first place.

Bentley knew he needed to deliver something new if he was going to last in the industry. His career has spanned over two decades, not only because of his willingness to evolve, but also for being mainstream country’s “consummate good guy” and someone who fans could relate to. Bentley’s flexibility and genre blending, even early on in his career (his album Up On the Ridge from 2010, which reached No. 9 on the US Billboard 200 and No. 2 on the US Country charts) is more bluegrass-influenced.

The album features several bluegrass collaborations, including “Pride (In the Name of Love)” with Punch Brothers and Del McCoury, and “Senor (Tales of Yankee Power)” with Chris Thile and Punch Brothers.

Additionally, Bentley was chosen to deliver a tribute to Merle Haggard during the 2016 CMT Awards because of his authentic connection to country music traditions, and his songs are also generally favored to those of his peers.

Bentley’s eighth studio album, Black, was seen as a significant departure from his usual sound. There were criticisms with some describing it as “pretty terrible” and potentially his “worst record ever.”

The lead single “Somewhere On A Beach” was also considered problematic and with inappropriate sexual references: “Got a new girl, she got it goin' on / We drink all day, and party all night / I'm way too gone to have you on my mind / She got a body and she's naughty / And she got me like you ain't never got me / I'm gettin' sun, gettin' some, and I ain't slept in a week / Yeah, I'm somewhere on a beach,” which reportedly disappointed longtime fans who expected better from him.

The album tested fans' loyalty and goodwill by crossing perceptible lines of creative decency. Nevertheless, the album was critically and commercially successful and became his highest-charting album on the Billboard 200. It also achieved Platinum certification by the RIAA.

His ninth studio album, The Mountain, represented a comeback after the disappointing Black album. It wasn’t a dramatic return to bluegrass (or an obvious attempt to win back his fans’ trust); rather, it was a return to what Bentley does best.  

Inspired by his trip to the legendary Telluride Bluegrass Festival, his experience translated into songs that focus on persevering over difficulties, showing appreciation for those who matter, and reflecting on your life.  

Jon Randall was brought in as a producer to balance out the contemporary influence brought by the album’s co-producer, Ross Copperman. Noteworthy songs from the album include “Stranger To Myself,” “The Mountain,” and “Travelin’ Light,” his collaboration with Brandi Carlile. The album debuted at No. 3 on the Billboard 200 and achieved No. 1 on the U.S. Country charts with a RIAA Gold certification.

In 2023, Bentley embraced the collaborative spirit that other country music artists had also welcomed. His partnership with Billy Strings for “High Note” earned them a Grammy nomination for Best Country Duo/Group Performance. Collaborations became so popular that only one nominee in the Best Country Duo/Group Performance category at the 66th GRAMMY Awards was an actual full-time group (Brothers Osborne), with the rest being pairings of individual artists.

This year, he released THE SESSIONS, a four-song live collection featuring “What Was I Thinkin’,” his chart-topping collaboration with Jordan Davis, his cover of Keith Whitley’s “I’m No Stranger to the Rain,” “Heartbreak Drinking Tour,” and “Get Down On Your Knees and Pray” with The Band Loula.

Bentley may be responsible for country music’s massive success in 2023, when the genre had its biggest year in over a decade with massive mainstream crossover success. After 48 years, more country artists have racked up more No. 1 hits on Billboard’s all-genre Hot 100 chart. Covers and tributes also became popular, bridging the gap between generations of fans.

The momentum continued in 2024, with 25% of the Top 40 country songs being by artists who had not previously appeared on charts, giving more up-and-coming country music artists a chance. Bentley is one of the artists leading the renaissance since he’s an artist who bridged different eras and styles of country music without forgetting his roots, and while also adapting to music trends.  

Bentley’s 20-year career demonstrates he knows a thing or two about staying relevant and successful in the music industry. His journey from mainstream darling to creative missteps, and back again, shows there is artistic redemption in country music as long as you stay authentic and know how to return to your roots.  

His ability to bridge different eras, collaborate with diverse artists from different genres, and maintain (or in his case, restore) credibility with both critics and fans positions him as a lasting figure in country music who isn't afraid to take some risks.