When your career spans nineteen years, nine studio albums, and 33 singles, it must be hard to pick songs to play live in concert. I know…not a bad problem to have. But I’m guessing, that must be what it’s like for Dierks Bentley. Dierks is headling our Country 1025 Country Music Fesitival tomorrow (June 24), for the 2nd time at the Xfinity Center.  Eighteen of Bentley’s singles have gone to #1, so there’s that problem, too. And we all know, artists love to do sing-a-long cover songs. Add two or three of those to the potential choices list. So, we are talking potentially 35 songs from which to pick!

Electing 5 favorites from Dierks Bentley’s vast catalog to share with you, isn’t going to be easy. But I’m up for the task. We’ve been playing Dierks’ music on the station since his very first single, released in 2003. Who could forget “What Was I Thinkin’?” It’s such a fun, upbeat jam, and it went to #1 fairly quickly, right out of the gate. Obviously, he will be performing this tomorrow night. And no fair looking for the setlist online! Over the course of ninetten years, Frederick Dierks Bentley from Phoenix, Arizona, has delivered hit after hit, ranging from fun, to inspirational, love songs to sexy slow jams.

If you are putting together a preshow playlist for our Country 1025 Country Music Festival, you may consider my 5 favorites from Dierks Bentley, listed here.

Country 1025 Country Music Festival 2015 with Dierks Bentley  

• 1. What Was I Thinkin'

  There’s nothing like your first, so I’m told. It was the first of many firsts for Dierks. His first single release, his first #1, the first time he heard his song on the radio, and the first time people sang one of his songs back to him.

  Enjoy this 2003 gem

• 2. I Hold On

  I’m not sure exactly why this one hits me so hard, but it does. Perhaps it’s the attachment to the material things in our lives that have memories and meaning to us. Or perhaps it’s the connection between Dierks and his dad here that resonates. It could simply come down to the melody, too.

  Here’s “I Hold On”… I may get emotional.

• 3. Free and Easy

  It’s about the freedom of youth, throwing responsibiltiy to the wind, and the open road. What’s not to love here, in this Dierks 2007 #1 hit from his Long Trip Alone album. And the music on this throwback is a total bluegrass bumpin’ summer jammer. Completely infectious, there’s no way not to crank it up in the parking lot when you are tailgating.

• 4. Burning Man

  The collaboration between Dierks and Brothers Osborne just puts a spell on me. Their voices together, John’s guitar work… It’s all just magical. Hearing it live when they both toured with Kenny Chesney at Gillette Stadium in 2018, only elevated my love for this song. Leaves me speechless.

   

• 5. Riser

  Not every song on a preshow playlist has to be a banger. Everyone of us occasionally needs that one song we can go to for inspiration, to get us through tough times, to heal. And not every song on a playlist has to be a huge hit. This one barely edged into the top 25 in 2015, but it’s certainly unforgettable. Beautifully written with haunting melodies. It’s an often overlooked work of art, and the title track from Bentley’s 2014 album.

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