In 1994, a not yet 20-year-old Dierks Bentley threw all caution to the wind when he packed up his dorm room at the University of Vermont with hopes to never return. Bentley’s relocation would not only forever change the course of his life – it would go on to catalyze his tremendous impact on roots music at large.

After a trip with his father to Nashville made quite the impression, Bentley decided to complete his college degree at Vanderbilt, dedicating his studies to English (the major most proximal to songwriting). After graduating, Bentley continued to foster both his musical education and career; his day job entailed archiving old country performances at The Nashville Network (in fact, his diligent field work even got him banned temporarily from the Grand Ole Opry on counts of trespassing), while his evenings were filled with bar gigs and songwriting sessions. After five years of grunt work, 2003 saw Bentley release a self-titled album with Capitol Records. His first single, “What Was I Thinkin’,” made waves on the country charts. Since then, Bentley has been responsible for the release of 20 No. 1 country singles and 10 additional studio albums, the latest of which, Broken Branches, arrived in June.

While Bentley’s career has seen major commercial country success, his deep respect for expansion and immersion has made him a beloved fixture within bluegrass, as well.

Of his instrumental move to Nashville, Bentley has shared, “I moved to Nashville in 1994 – I was trying to find that seed of truth, that authenticity, that thing ‘country music’ that I had in my head. And I got here and it was definitely different than I expected it to be. It’s big business, a lot of money.

“Luckily, for me, I found a little bar called the Station Inn where bluegrass music existed – and I found what I was looking for. Just the sound of a five-piece bluegrass band blew my mind. And they’re not trying to take meetings all the time and meet producers, and get their foot in the door. It’s funny, I moved to Nashville looking for country music, but I found bluegrass.”

Whether it’s his proclivity for cross-genre conversation, songwriting prowess, or patinaed tenor delivery, Dierks has proved himself a mainstay favorite for country, Americana, and bluegrass fans – here at Good Country and BGS, and beyond. In honor of his recent album release and his huge Broken Branches tour with Zach Top and the Band Loula concluding this month, we present you with our Dierkscography, a non-comprehensive compilation of more than 15 songs meant to show off some of our favorite Dierks gems from across genres sampled from the many years of his remarkable career.

“Never You” featuring Miranda Lambert, Broken Branches (2025)

Dierks’s new album, Broken Branches, arrived fresh off the press with a slew of impressive collaborators. From Riley Green to Stephen Wilson Jr., Dierks fondly calls the record a “special” display of “making music in the studio with our buddies.” Country giant and long-time collaborator Miranda Lambert joins Bentley on this banjo-driven track, the pair’s velvety duet vocals imbuing tenderness and warmth into one of the album’s only love songs.

“High Note” featuring Billy Strings, Gravel & Gold (2023)

This rip-roaring tune off of Bentley’s tenth studio album features a whole handful of bluegrass greats. Not only does Billy’s high tenor soar above Dierks gravelly tones during choruses, his famous flatpicking joins the likes of Sam Bush, Bryan Sutton, and Jerry Douglas for a superjam ending.

Of the collaboration, Dierks recalls, “Bryan Sutton first tipped me off to Billy Strings about seven years ago, mentioning that the future of bluegrass was in good hands. I was totally blown away the first time I saw him. I’ve cut songs like these since my first record, and I knew I wanted to have him on this one, I’m such a huge fan. It was a lot of fun to have him, Jerry, Sam, and Bryan all passing licks around – having them all on this record means a lot to me personally.”

“American Girl” (2024)

Who doesn’t love an Americana “American Girl”? Bentley delivers this country-fied Tom Petty classic alongside some BGS favorites, including Chris Eldridge on guitar and Noam Pikelny on banjo. Dierks reprised the hit single joined by Bronwyn Keith-Hynes, Sierra Hull, and Molly Tuttle on stage at the 2024 CMA Awards, bringing down the house.

“For As Long As I Can Remember,” Broken Branches (2025)

The country canon has seen its fair share of heartache, murder, trains, and drinking. Also on his latest release, “For As Long As I Can Remember” shirks these motifs in favor of something a little more wholesome – a warm and adoring ballad dedicated to the strength of enduring familial bond. An ode to his brother and father, Dierks reminds that respect and love can be country, too.

“Train Travelin’,” Dierks Bentley (2003)

With many of his nascent Nashville days edified by nights at the Station Inn and in the surrounding bluegrass scene, iconic bluegrass family the McCourys quickly became repeat collaborators for Dierks. Their features pepper many of his earlier albums, dating all the way back to his debut self-titled release in 2003. “Train Travelin’” would become the first of many, with other gems such as Good Man Like Me (Modern Day Drifter, 2005) and Last Call featuring Ronnie McCoury (Feel That Fire, 2009) dotting the road to Bentley’s eventual bluegrass-centric album, Up On The Ridge.

“Up On The Ridge,” Up On The Ridge (2010)

The titular track off of Bentley’s bluegrass-inspired album is thrumming with energy, both quickly-paced and haunting with its descending melodic hook. Up On The Ridge was released as Bentley’s fifth studio album, featuring a star-studded list of bluegrass collaborators including Alison Krauss, Punch Brothers, Chris Stapleton, Tim O’Brien, Sam Bush, and beyond. Del McCoury even joins forces with Bentley and Punch Brothers to deliver a deliciously grassified cover of U2’s “Pride (in the Name of Love)” further evidencing the album as a culmination of both tradition and innovation.

“Freeborn Man,” (Live, 2025)

Another of our favorite timeless covers, Dierks has been adorning his Broken Branches Tour this summer with his vigorous take on “Freeborn Man.” This rendition includes a fiery feature by Zach Top, nearly toppling the stage with talent.

“Hoedown for My Lowdown Rowdy Ways” featuring Dierks Bentley, Lowdown Hoedown (Jason Carter, 2022)

With Jason Carter fiddling his heart out on Dierks’ records since 2003, it’s of course a polite roots custom for Dierks to return the favor. Released as part of Carter’s second solo album, Lowdown Hoedown, “Hoedown for My Lowdown Rowdy Ways” has Dierks singing harmony and strumming away on the bluesy breakdown. Lowdown Hoedown also features a tender Jamie Hartford number, “Good Things Happen,” that Dierks Bentley covered on his 2005 album Modern Day Drifter, yet another frame of conversation between the two artists.

“Prodigal Son’s Prayer” featuring The Grascals, Long Trip Alone (2006)

This acoustic tune features the bluegrass sensibilities of the Grascals, a long-running group lauded for their instrumental prowess. The song tells a tale that loosely follows that of the Bible parable of the prodigal son, ultimately centering themes of repair and reconciliation. In addition to the Grascals, the song also features the stomps and hums of incarcerated individuals from Charles Bass Correctional Complex, who had been in Bentley’s producer’s Bible studies course at the time.

“Free and Easy (Down The Road I Go),” Long Trip Alone (2006)

From the same release, this breezy banger remains a hallmark of Bentley’s career, even after nearly two decades since it dropped. The fifth of his singles to top the US Billboard’s Hot Country charts, “Free and Easy (Down The Road I Go) lures in listeners with its fast-paced country twang and life-affirming sentiment.

“Beautiful World” featuring Patty Griffin, Feel That Fire (2009)

No stranger to incredible collaborators, Dierks Bentley asked iconic folk and country singer-songwriter Patty Griffin to accompany him on this track, gushing, “Her voice is one of a kind and she’s such an important figure in the American music scene… She’s just amazing. And so I asked her.”

The result is a tender homage to the beauties of the world, largely inspired by his wife, who was pregnant with their daughter at the time of the song’s conception. “You hear people sometimes say, ‘Man, I can’t imagine bringing a child into this world. It’s so bad.’ That’s just such a negative outlook,” Dierks says. “You cannot live your life with that viewpoint of the world. Yes, there are a lot of things that are wrong, but it is a beautiful world, and you need to find the positive in it.”

“Heart of a Lonely Girl,” Home (2012)

From Bentley’s sixth studio album, Home, comes this spirited while emotionally deep number. A narrative song, it was penned by the infinitely talented Charlie Worsham, who would go on to join Bentley’s touring band a decade later – and you can currently see him on stage each night during the Broken Branches tour.

“Trip Around the Sun,” featuring Dierks Bentley, I Built a World (Bronwyn Keith-Hynes, 2024)

Fiddler Bronwyn Keith-Hynes first connected with Bentley through Molly Tuttle & Golden Highway, the popular bluegrass group having opened for him several times on tour over their three-and-a-half year run. She’s also married to Jason Carter, so Dierks wasn’t just a professional collaborator, but a member of her personal Nashville network, as well. It’s no surprise, then, that she’d end up on stage with him at the CMA Awards and, in the same year, he would guest on her acclaimed and GRAMMY Award-nominated album, I Built a World.

“Mardi Gras” featuring Trombone Shorty, Black (2016)

Soaked in Louisiana charm, this tune was inspired by Dierk’s 2015 galavant on a Mardi Gras parade float. Featuring the indelible hornsmanship of Trombone Shorty, the track grooves along with bluesy undertones. “Getting Trombone Shorty to do his thing on it, what a great guy. I love working with him. He is so laid-back and so good at what he does,” Bentley boasts of his collaborator.

“Travelin’ Light” featuring Brandi Carlile, The Mountain (2018)

Featuring the powerhouse vocals of Americana giant Brandi Carlile, this tune appears on Bentley’s 2018 album, The Mountain. The collaboration between the two icons came to fruition after Bentley saw Brandi perform at Telluride Bluegrass Festival, inspiring him to approach her about dueting on the track.

“Sun Sets in Colorado,” Gravel & Gold (2023)

Written reflecting his pandemic move to Colorado (though he has since returned to Nashville), Bentley released this tune on Gravel & Gold. The song shouts out New Grass Revival and Telluride in a verse: “Sing an old new grass song with me/ Telluride along with me,” while also featuring New Grass Revival founding member Sam Bush on mandolin. Bryan Sutton also joins in on the studio recording, yet another sparkling collab with bluegrass greats.

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Photo Credit: Robby Klein