Best of Dierks Bentley Playlist

Liven up your music library with these top tracks

Dierks Bentley released his self-titled debut album in 2003. The first single, "What Was I Thinkin'," shot straight to No. 1 on the charts and there was no looking back. The rest, as they say, is history. Since then Bentley has become one of country music's most consistent hitmakers.

The following fifteen tracks, listed in alphabetical order, are my absolute favorite Dierks Bentley songs. These tunes create the ultimate Dierks Bentley playlist.

01
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"Cab of My Truck"

Modern Day Drifter
Vala M/Wikimedia Commons/Fair Use

"Cab of My Truck" appears on Bentley's 2005 album Modern Day Drifter. In it Bentley sings about the love he has for his truck and how everything he needs is inside: his Johnny Cash box set, his Red Man chew and his girlfriend sitting right beside him.

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02
of 15
"Come a Little Closer"

Come A Little Closer
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This song is definitely one of the sexiest songs Bentley has ever recorded. He sings, "Come a little closer baby / I feel like layin' you down on a bed of sweet surrender / Where we can work it all out." It's no wonder "Come a Little Closer" spent an impressive three weeks at No. 1.

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03
of 15
"Every Mile a Memory"

Every Mile a Memory
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This song became Bentley's fourth No. 1 single. "Every Mile a Memory" talks of being out on the road, away from the one you love and how everything you see reminds you of them. "Every day, a page turned down / Every night, a lonesome sound / Like a freight train rollin' through my dreams."

Download "Every Mile a Memory"

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04
of 15
"Feel That Fire"

Feel That Fire
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In "Feel That Fire," Bentley's sixth No. 1, he sings about giving his lady everything she needs. He wants to make sure she knows that she's everything to him, and he'll give her anything she needs.

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05
of 15
"Free and Easy (Down the Road I Go)"

Long Trip Alone
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"Free and Easy" is an apt title, as Bentley sings and living his life on the road. Nothing is tying him down; life is just as easy as a country stroll. This song is a prime slice of Bentley's signature easygoing sound.

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06
of 15
"How Am I Doin'"

How Am I Doin'
Publichall/Wikimedia Commons/Getty Images

"How Am I Doin'" is the third and final single from Bentley's self-title debut album. It peaked at No. 4. The song is the perfect kiss-off song. A girl who broke his heart comes back into his life. He tells her that sometimes he cries, but that they are tears of joy as he's no longer under her thumb.

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07
of 15
"I Bought the Shoes"

Dierks Bentley
Vala M/Wikimedia Commons/Fair Use

"I Bought the Shoes" appears on Bentley's debut, and while it was never a single, it's one of my favorite songs on the album. He laments about everything he bought his wife, from designer clothes to fancy cars, to the golden ring on the hand that closes the door and the shoes that walk out on him.

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08
of 15
"Long Trip Alone"

Long Trip Alone
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This song talks about life being a long journey: one that seems even longer if you are going it alone. He asks his lady to walk with him a while because it's not the same without her there.

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09
of 15
"Lot of Leavin' Left to Do"

Lot of Leavin' Left To Do
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In "Lot of Leavin' Left to Do," which peaked at No. 3, Bentley tries to tell his love interest that he's not ready to settle down. He has miles to go, and he'll only break her heart if she thinks she can tie him down.

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10
of 15
"My Last Name"

My Last Name
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"My Last Name" is a feel good song about having pride in your roots. It was released as his second single for his debut album. In the song a bully makes fun of Bentley's last name. One of my favorite lyrics is "Passed down from generations / Too far back to trace / I can see all my relations / When I look into my face."

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11
of 15
"Settle for a Slowdown"

So so long
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This song appears on Bentley's sophomore effort, Modern Day Drifter. The heart-wrenching number became his third No. 1 single. In the song Bentley's girlfriend is leaving him and he's standing in the road looking at her drive away, hoping to see the "glow of the break lights." He hopes that she'll realize what she's missing, but she doesn't stop, or even slow down.

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12
of 15
"So, So Long"

So so long
Vala M/Wikimedia Commons/Fair Use

Another classic Bentley torch song. In this song, which appears on Modern Day Drifter, Bentley catches his girlfriend in a honky tonk dancing with some other guy when she told him she was working that night. Bentley says goodbye and tells her she'll miss him for so, so long.

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13
of 15
"Trying to Stop Your Leaving"

Long Trip Alone
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"Trying to Stop Your Leaving," the fourth and final single from Long Trip Alone, is about a relationship Bentley knows is ending. He waxes poetic about how he wants to stop her from leaving, but no matter what, nothing would be enough.

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14
of 15
"What Was I Thinkin'"

Dierks Bentley - Greatest Hits: Every Mile a Memory
Dierks Bentley - Greatest Hits: Every Mile a Memory. Capitol Nashville

This is Bentley's first song and it introduces us to the "little white tank top." He sings about sneaking out with a girl who had a really mean daddy that may have spent some time in prison. When he brings her back home, the father is waiting for her in the driveway, and he knows he's gonna have hell to pay. He sings, "'Cause I was thinkin' 'bout a little white tank top sittin' right there in the middle by me."

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15
of 15
"Wish It Would Break"

Dierks Bentley
Vala M/Wikimedia Commons/Fair Use

Bentley's relationship is over, but he can't let go of all the things that remind him of her: the picture on the wall, the special song on the radio. He tries slamming the door to make the picture fall down and banging on the radio when their song comes on, hoping that they'll break.

He sings, "This ole heart's got a mind of it's own / It's decided not to let you go / And even though your love's no longer here, it won't let me shed one tear / 'Cause it's still holdin onto yesterday / I wish it would break."

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