10. Dierks Bentley - "Bourbon In Kentucky"
While not exactly his biggest chart hit, this song from the pen of Hilary Lindsey, Gordie Sampson, and Ryan Tendell was perhaps Bentley at his most simple and straight-ahead, as the lead character explains that the heartbreak that he’s going through from a break-up is more potent than the alcohol he has consumed to try to get over her. Throw in the harmonies of Kacey Musgraves, and you have a record that should have been too good to be resisted.
9. Dierks Bentley - "Am I The Only One"
Ah, the growing pains of maturity. In this 2011 hit, Bentley is lamenting the fact that all of his friends that he has partied with it in the past now have other priorities, leaving the singer to celebrate life alone. Though, we think the crowd has never failed to keep him company during this one.
8. Dierks Bentley - "Lot Of Leavin’ Left To Do"
As the singer continued to grow as an artist, this Dierks Bentley song was very telling in the fact that he knew that he wasn’t quite ready to settle down with anyone just yet, with as many road miles that lay ahead for the singer. As it turned out, family was around the corner for Bentley, just not yet.
7. Dierks Bentley - "Drunk On A Plane"
Think 'Friends In Low Places' in a plane instead of a bar, and you’ve got this recipe for what led to one of Bentley’s biggest hits from 2014. A man decides to use the Cancun tickets he bought for his honeymoon anyway, and the fun begins. Helping illustrate this song even better was the award-winning video, which had us all grinning from ear to ear.
6. Dierks Bentley - "Different For Girls"
This collaboration with Elle King from Black is among Bentley’s more mature moments, showing the differences that men and women show in the dealing of a broken heart. The song should have led to a few awards, as Bentley raised his game with King on this career highlight.
5. Dierks Bentley - "Every Mile A Memory"
In this chart-topper from 2005, the singer is trying to outrun the pain he feels due to a broken relationship. But, no matter how many times the wheels turn around and around, he can’t seem to put his lover out of his mind. From a vocals standpoint, as well as production-wise, this just might be one of his finest moments.
4. Dierks Bentley - "What Was I Thinkin"
It was off to the races with a bang for Bentley with his 2003 debut single, a deep-fried song of lust in Alabama. The night goes from good to bad to worse, as the couple seem to attract a crowd. At the end of the song, you think that the protagonist has successfully won his freedom from the night, but with one smile, he’s hooked again – and we were too!
3. Dierks Bentley - "Black"
Maybe more than any Dierks Bentley song, this one is one of his most subtle and understated. We know that you have to have tempo in a career, but the singer always seems to shine brightest on the more serious moments. Comparatively speaking, this is Bentley at his most sparse – and also his most effecting.
2. Dierks Bentley - "Tryin’ To Stop Your Leavin'"
Written by the singer along with Brett and Jim Beavers, Bentley was quite convincing on this 2008 single about a man who knows the inevitable break-up is coming, but want to try to avoid the relationship’s end at any cost.
1. Dierks Bentley - "I Hold On"
They say that you are best served to write about what you know and what you have experienced. That couldn’t be more true than on this 2013 ballad about a man trying to stay true to the things and people in life that have gotten him this far. Perhaps the most emotional part of this song was Bentley remembering the truck that he came to Nashville in – and the father that made the trip with him (who had just passed away not long before the writing of the song).