The 10 Best Dierks Bentley Songs of All-Time

Dierks Bentley

Dierks Bentley was born on November 20, 1975, in Phoenix, Arizona. His music interest started with his father’s Hank Wlliams Jr. records. According to PBS, Bentley attended the University of Vermont for a year after transferring to Vanderbilt University and graduated in 1997. After graduation, he got a job at The Nashville Network doing research while playing bars and doing demos at night. The next five years were extremely rough. Bentley almost threw in the towel several times. However, he discovered the Station Inn, a premier spot for Bluegrass in Nashville. Over time, he became so discouraged that he wasn’t gaining fame from his singing that he might have given up on his dream if it hadn’t been for late-night jam sessions. Thankfully, he didn’t because his big break was just around the corner. However, in 2003 his self-titled started climbing the country music charts. Over nine albums, he has had 20 number 1 country songs. Moreover, almost every one of his albums was certified gold or platinum. Bentley has chartered his own career, never shying away from bold decisions. In 2010 he released the bluegrass album, Up on the Ridge. Even though Bluegrass isn’t one of the most popular genres of music, the album sold so well it almost made gold. On October 1, 2005, he became a member of the Grand Ole Opry, the youngest person to achieve this honor. It was the same year he won the CMA Horizon Award. A little over a decade later, he won the ACMA’s Merle Haggard Spirit award for his chart-topping career. Currently, he is more focused on his side project, Hot Country Nights. With all the songs on his albums, there are many amazing songs. These are the top 10 Dierks Bentley songs of all time.

10. Different for Girls (featuring Elle King)


This song is a poignant battle of the sexes ballad. The lyrics are about the differences when a breakup happens; women take it more to heart, and men just blow it off and move past it. The collaboration with Elle King adds additional depth to the song. King and Bentley met at a studio in Austin to record this song. This was the first time King had done a country song and her voice compliments Bentley’s perfectly.

9. Free and Easy (Down the Road I Go)


The combination of banjo and guitar at the beginning of this song gives it a light feel. The lyrics are about someone who chooses to go through life without a care in the world. Additionally, it’s about being present in life and keeping an optimistic view of life. Many artists would choose a guitar for the fill-ins, but the banjo adds a uniqueness that creates a fusion country bluegrass song.

8. Black


As the song opens, drum riffs and guitar licks meld for a sound that sounds like a breeze. This is one song in his catalog where he strips down the vocals and instrumentations. The lyrics are sensual weave in and out of the music to create a love song many country stars wouldn’t execute.

7. Living


Simple guitar riffs in this song lend themselves perfectly to lyrics about enjoying the simple things in life and enjoying the freshness of little moments and realizing they can be the last. So many times, people get lost in the small details of life and forget how the simple things are what life’s really about. The lyrics in this song are a tribute to everyday moments.

6. 5-1-5-0


The title of this song is a play on 51/50 or going crazy. It’s head over heels in a love country song that stays fresh and fun throughout the uptempo beats. Bentley wrote this song with Jim Beavers, who collaborated on several of his other songs.

5. Burning Man (Featuring Brothers Osborne)


The song starts off with a slow beat which, after exploring how life is, a series of questions goes into eclectic guitar riffs and brief punctuations of drums that sound like lightning on the track. The refrain of the song is about the yin and yang, light and darkness in everyone. Near the end of the music, it opens up into ethereal guitar solos. It closes with the song’s refrain as reminding people that everyone is who they are and appreciate themselves.

4. Gone


The melancholy guitar opens this song. The lyrics are about the ties that depression can take on us when someone leaves us. Bentley’s honest vocals are easily relatable because people often do unexpected things when they lose someone who meant the world. However, most of the things we do are because we’re overthinking the situation and not because we need to stay stuck in the moment.

3. Somewhere on a Beach


Living well is the best revenge, or so the old phrase goes. This song is about just that. Even though the guitar and vocals are melancholy, the lyrics are about the ultimate wish, going on a vacation to forget someone, and losing yourself in fun new experiences to move on with your life.

2. What Was I Thinkin’


It’s easy to get wrapped up with a bad boy or girl because we like the danger. This song is a campy tribute to the Bonnie and Clyde relationships that get us in a lot of trouble but are so much fun we can’t help but fall for them. The instrumentation in this song is a traditional country with slide guitar and low essential drum licks.

1. Drunk on a Plane


The opening guitar riffs sound boozy, which works well for a song that’s about someone who goes on their honeymoon alone because the wedding fell through. Bentley’s inventive music makes something like getting jilted at the alter sound upbeat and even a little bit funny. With such a catchy beat, it’s easy to see why this is one of his signature songs.

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