Top 10 Songs by Dierks Bentley

Dierks Bentley is one of the most popular country artists of the 2000s, not just for his hit songs, but also his ability to blend genres. In a career that currently spans 20 years, Bentley has keenly merged country, bluegrass and rock into his sound, demonstrating his love not only for those genres, but music at large.

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Since he debuted onto the country scene in 2003 with his hit single “What Was I Thinkin’,” Bentley’s stamina has only gotten stronger. Below, we look at 10 of Bentley’s best songs.

1. “Still”

Bentley gets introspective on his 2023 album, Gravel & Gold, and “Still” demonstrates this beautifully. With just an acoustic guitar and his soft voice, the singer turns to nature to calm his hectic mind, taking us inside his head as he find the stillness he craves.

“Still” feels like a meditative song born from a need for peace and solace, which Bentley finds through the music. “Still” has the same impact on the listener, offering a sense of peace we all need.

When there’s no peace to be found
I head for hallowed ground
I still feel at home up on some lonely hill
In the blink of an eye, my head’s clear as the sky
Like the trees with no breeze, my heart is still
Where the world’s the way God made it still

2. “Burning Man” ft. Brothers Osborne

As part of Bentley’s critically acclaimed 2018 album, The Mountain, it can be hard to find a song that stands above the rest. But “Burning Man” certainly makes a compelling case. This soaring collaboration with Brothers Osborne is the perfect blend of expert musicianship and meaningful lyricism. With John Osborne holding the tempo on guitar, brother T.J. Osborne’s voice unites with Bentley’s, elevating the song’s meaning about living in between stability and being free-spirited. The song is electrifying and is one of Bentley’s finest offerings.

I’m a little bit steady but still little bit rolling stone
I’m a little bit heaven but still a little bit flesh and bone
Little found, little don’t know where I am
I’m a little bit holy water but still a little bit burning man
Burning man

3. “Free and Easy (Down the Road I Go)”

Like “What Was I Thinkin,'” “Free and Easy” is one of Bentley’s most identifiable songs. This breezy country song uses nature as a metaphor for the feeling of pure freedom, whether he’s hangin’ memories on the high line poles or has got the sun shinin’ on me like a big spotlight.

There’s a jovial spirit Bentley channels into the song that he wrote with Brett Beavers, Rob Harrington, and Rod Janzen that makes you believe what he’s singing. It’s become one of his signature hits–and one of the best of his career thus far.

Ain’t no tellin’ where the wind might blow
Free and easy down the road I go
Livin’ life like a Sunday stroll
Free and easy down the road I go
Free and easy down the road I go

4. “Walking Each Other Home”

“Walking Each Other Home” is one of Bentley’s most heartfelt offerings. Here, Bentley explores all of the companions he’s had throughout life, from an insightful book of poems written by Jack Kerouac and his first love who taught him about hope, to the second verse about two elderly men who become new friends after their wives died.

Bentley gently hits a nerve with “Walking Each Other Home,” conveying our need for community and friendship to get through life, as told through tear-inducing lyrics. Though newly released, “Walking Each Other Home” already sets itself apart as one of Bentley’s most touching, best songs.

So take the low road, take the high road
Take whatever road you’re on
Sometimes the wrong one leads you right
Sometimes the right one leads you wrong
And the world just keeps on spinnin’
So find a hand for holdin’ on
‘Cause we’re all just walkin’ each other home
Walkin’ each other home
We’re all just walkin’ each other home

5. “I Hold On”

As one of Bentley’s signature hits that’s been certified two times platinum by the RIAA, “I Hold On” serves as a personal tribute to the mementos Bentley holds dear, whether it’s an old beat-up truck he drove across the country with his dad when he moved to Nashville to pursue his dreams or the rusty strings he was still playing when he released the song in 2013. The song follows the singer as he reflects on his career more than 10 years in as he still has a lot of stories to tell, making it quintessential Bentley.

To the things I believe in
My faith, your love, our freedom
To the things I can count on
To keep me going strong
Yeah, I hold on
I hold on

6. “What Was I Thinkin'”

“What Was I Thinkin” is one of Bentley’s most instantly recognizable songs, and for good reason. A standout in the early 2000s country landscape, “What Was I Thinkin” was released as his debut single in 2003. This tongue-twisting tune comically follows a man who has a wild night out with an unpredictable woman. Ranging from a bar fight to being chased by the police, the story is anchored by the line I know what I was feelin’ / But what was I thinkin.’ It also became his first No. 1 hit, Bentley setting himself up as an artist to keep an eye (and ear) on for years to come.

‘Cause I was thinkin’ ’bout a little white tank top
Sittin’ right there in the middle by me
I was thinkin’ ’bout a long kiss
Man, just gotta get goin’ where the night might lead
I know what I was feelin’
But what was I thinkin’?
What was I thinkin’?

7. “Up on the Ridge”

Bluegrass is as integral to Bentley’s sound as country music is, and he proved how much he appreciates the genre when he made a bluegrass album with Up on the Ridge in 2010. A true passion project for the singer, he shows off his diverse musicality on the title track.

Bentley’s love for nature shines through, taking his lover away from the city lights up to where the air is still. It’s a solid country-bluegrass song that pushed Bentley past his boundaries in a way that made for intriguing music, making “Up on the Ridge” one of his best.

Won’t you come with me tonight
Where moonlight drifts into your eyes
I just want one little kiss
When we get high up on the ridge

8. “Home”

Bentley gave fans a peek inside his heart with “Home.” Inspired by the tragic shooting in his home state of Arizona in 2011 that left six people dead and critically injured, including now-retired Rep. Gabby Giffords, “Home” sees Bentley offering his poignant take on the country through this patriotic tune. Looking over the earth’s vast landscape that he admits has got her scars, Bentley still sees the beauty of life through the darkness, as told through his gentle voice. This sentimental number is a heartfelt standout in Bentley’s catalog.

From the mountains high
To the wave-crashed coast
There’s a way to find
Better days, I know
It’s been a long hard ride
Got a ways to go
But this is still the place
That we all call home

9. “How Am I Doin”

This oldie-but-goodie turns a searing heartbreak into this rollicking country number. Bentley continues to show off his ability to craft a clever lyric in the vein of “What Was I Thinkin,'” proving that while he was bruised by his cheating ex-lover, he’s getting over her just fine. The melody is irresistible and dance-friendly, making you want to spin your way around the dance floor. It’s an early 2000s country bop that still holds up in Bentley’s live shows.

Well how am I doin’ since you did what you done to me?
I can’t lie I sometimes cry when I think of how it used to be
I keep my friends with me, I stay busy and I don’t get much sleep
Baby, that’s how I’m doin’ since you did what you done to me

10. “Lot of Leavin’ Left to Do”

Bentley is a man born to run on “Lot of Leavin’ Left to Do.” In this early career hit, Bentley confesses through the lyrics that he’s not one to be tied down, as his old boots still got a lot of ground to cover and is admittedly hard to handle. Bentley is forthcoming about being wild and free, saying point blank so before you go and turn me on / Be sure that you can turn me loose. The song sounds like his personal story of life on the road wrapped around a classic country melody.

And as long as there’s a song
Left in this old guitar
This life I’m bound to lead
Ain’t for the faint of heart
So you won’t fall for me
If you know what’s good for you
‘Cause I still got a lot of leavin’ left to do

(Photo by Erika Goldring/Getty Images for ACM)

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