17 Dierks Bentley Number One Songs Ranked

• 17. “Woman, Amen” (2018)

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  A song Dierks co-wrote; his wife inspired it. But as he notes, "I've come back from so many writing appointments over the past 12 years like 'I wrote this song about you,' and she's like, 'Just because it's a love song doesn't mean it's about me.'"

• 16. “Am I the Only One” (2011)

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  Bentley told Billboard at the time, that following his bluegrass album 'Up on the Ridge,' he wanted to "be back on the radio, and I wanted my fans to hear our stuff. I wanted to come back with a song that was fun for fans." And this was definitely a fun song.

• 15. “I Hold On” (2013)

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  This song describes the singer staying true to what he enjoys and is comfortable with, including an old truck, an old guitar, and his lover. The truck referenced is his 1994 Chevy Silverado that he and his late father drove to Nashville. He still drives it today.
• 14. “Somewhere on a Beach” (2015)

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  Dierks sings to his ex-girlfriend about his life after they broke up in this song. He tells her he has a new girlfriend and adds that she and he are together having fun together "somewhere on a beach."

• 13. “Come a Little Closer” (2005)

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  This was one of Bentley's early hits, and Billboard compared the sexiness of the tune to that of the late Conway Twitty.

• 12. “Sideways” (2009)

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  The song is about the male character's attempt to talk to a female in a bar. Despite not being able to hear her name because of the loud noise, he still tries to come on to her, saying that he wants to "get a little sideways" with her.
• 11. “Home” (2011)

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  A native Arizonian, Dierks says he was inspired by the Tucson, Arizona shooting that killed six people and critically injured U.S. Representative Gabby Giffords in January 2011.

• 10. “Feel That Fire” (2008)

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  To promote the single, Bentley shipped more than 2000 boxes of Cracker Jacks to various radio stations (a reference to "she wants the toy in the Cracker Jack," a line from the song).

• 9. “Settle for a Slowdown” (2005)

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  One more of Dierks' early chart-toppers, this song's music video paints a picture of a woman leaving him and their trailer in the desert for Hollywood. Bentley eventually shows up in Hollywood at a mansion and sings the chorus.
• 8. “Say You Do” (2014)

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  Dierks said at the time of this song's release that "Say You Do" was the song on his album 'Riser' that he loved from the very beginning. He added that he and his camp knew it would be a single; they just had to find the right time for it.

• 7. “5-1-5-0” (2012)

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  This is a fun song about just going crazy. The title references the 5150 "involuntary psychiatric hold" in the California Welfare and Institutions Code.

• 6. “Different for Girls” (featuring Elle King) (2016)

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  Elle King was the perfect choice for a duet partner on this song. This song gave Bentley a win for "Vocal Event of the Year" at the 2016 CMA Awards. It was also nominated for the 2017 Grammy Award for Best Country Duo/Group Performance.
• 5. “Living” (2019)

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  Something we should all do more of, "Living," is right on the mark. The song's official video features Dierks and his then 5-year-old son Knox playing together in the backyard, a water park, a go-kart track, and a laser tag arena.

• 4. “Drunk on a Plane” (2014)

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  An up-tempo gem from Bentley. The song is about a man who is left behind at the altar and takes a trip to Cancún alone after he cannot obtain a refund for the airplane tickets he had purchased for a honeymoon.

• 3. “Every Mile a Memory” (2006)

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  Quite an emotional ride, the song tells the story of a man missing a woman and how everything he sees and hears evokes her memory. Great song to listen to if you are feeling heartbreak.
• 2. “What Was I Thinkin'” (2003)

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  Bentley's very first radio single, and he scored a chart-topper right out of the box. The fun lyrics reference 1980's TV show 'Dukes Of Hazard' and sparked a friendship with actor John Schneider, whose character is referenced in the lyrics "like Bo Duke sliding over the hood."

• 1. “Free and Easy (Down the Road I Go)” (2007)

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  The song was made available as downloadable content for the "Rock Band" video game on December 16, 2008; it's a favorite of many of his fans.