Dierks Bentley songs are some of the most daringly original tracks in the last two decades of country music. Since his debut in 2003, the singer-songwriter has consistently defied radio trends to produce some of the most sonically interesting records in contemporary country music.

Bentley has wandered around stylistically, touching on uptempo party anthems, slow and sensual romantic songs and even bluegrass. But no matter the style, his records are all characterized by an uncompromising quality that sets him apart from any other artist currently working in Nashville.

Our list of the Top 10 Dierks Bentley Songs pulls the best tracks from across his entire career.

  • 10

    "How Am I Doin'"

    From: 'Dierks Bentley' (2003)

    The third single from Bentley's debut album was his second Top 5 country hit in a year. Written by Bentley with Writer X --  a pseudonym of Nashville tunesmith Jim Beavers -- the track is a sonic extension of "What Was I Thinkin'," and Lauren Elaine reprised her role of Becky in the video. The song reached No. 4 in the country charts.

  • 9

    "Lot of Leavin' Left to Do"

    From: 'Modern Day Drifter' (2005)

    Bentley gave a warning to any potential love interest in the lead single from his sophomore album. The lyrics portray him as someone whose nomadic lifestyle doesn't lend itself to long relationships: "So lovin' me might be a long shot gamble / So before ya go and turn me on / Be sure you can turn me loose / 'Cause I still got a lot of leavin' left to do."

    Written by Bentley with his producer Brett Beavers and Deric Ruttan, the song introduced an element of bluegrass to his sound. It peaked at No. 3 on the Billboard Hot Country Songs chart.

  • 8

    "I Hold On"

    From: 'Riser' (2014)

    The second single from Bentley's 2014 album Riser is a deeply personal track that talks about faith, love and freedom. Bentley wrote the song with Brett James, and he considers it a personal manifesto of sorts: "At first listen, you might think it’s about my truck or my guitar," he says, "but it’s really about why I do some of the things I do and the kind of guy I am."

  • 7


    From: 'Home' (2012)

    The third single from Home reached back to the sound that had helped establish Bentley as one of country's most unique artists a decade earlier. Written by Bentley and his frequent collaborators, Jim and Brett Beavers, the song uses the police code for a mentally unstable person as the catchphrase for a rowdy, good-time party song that featured an equally fun video. The energetic track reached No. 1 on the country charts and was certified as a gold single.

  • 6


    From: 'Black' (2016)

    "Black," like the No. 2 song on this list (keep reading!), finds Bentley leaning into his sensual side. The lyrics plead for a night of passion: "Make my world go black, hit me like a heart attack / Knock me flat on my back / Yeah, just keep doin' that," he sings over a moody melody.

    Bentley co-wrote "Black" with Ross Copperman and Ashley Gorley. It's the title track of his 2016 album, and also a nod to his wife, whose maiden name is Black.

  • 5

    "Every Mile a Memory"

    From: 'Long Trip Alone' (2006)

    The first single from Long Trip Alone found Bentley missing someone he loved while they were apart, and being reminded of her everywhere he looked: "Oh, every mile, a memory /  Every song, another scene / From some old movie going back in time / You and me." Another co-write with Bogard and Brett Beavers, the track reached No. 1 on the singles chart the same week its parent album captured the top spot on the country albums chart.

  • 4

    "Free and Easy (Down the Road I Go)"

    From: 'Long Trip Alone' (2006)

    After several slower, more ponderous singles in a row, Bentley returned to what he does best with this uptempo, fun song, which exemplifies his life philosophy: "I could make a million or wind up broke / Free and easy down the road I go / Can't take it with you when you go, so / Free and easy down the road I go." Written with Brett Beavers, Rob Harrington and Rod Janzen, the song was a huge hit, reaching No. 1 on the country charts.

  • 3


    From: 'Home' (2012)

    The title song and second single from Bentley's sixth studio album is one of the most powerful songs of his career. Inspired by the Tucson shootings that killed six and injured Gabrielle Giffords, the song mixed themes of pride and patriotism into a new approach for Bentley. The result was a track that reached No. 1, was certified gold and earned nominations for both Single and Song of the Year.

  • 2

    "Come a Little Closer"

    From: 'Modern Day Drifter' (2005)

    The second single from Bentley's second album is a slow ballad that gives him room to display a different side of his voice. His approach has often been compared to the sensual vocal style of Conway Twitty, while the song's video cast him as a romantic leading man and helped cement his position as one of country's hottest male stars. "Come a Little Closer" became a No. 1 hit for Bentley.

  • 1

    "What Was I Thinkin'"

    From: 'Dierks Bentley' (2003)

    Bentley's debut single from 2003 remains the definitive song of his career. With this track, he not only hit No. 1 with his very first song, he also helped to break commercial radio's stranglehold on a certain type of sound, which had been stagnating for years prior. Bentley's fresh arrangements and approach helped to open the floodgates for a sea change at country radio, qualifying this as the very best of the Top 10 Dierks Bentley Songs.

More From WQCB Brewer Maine