Dierks Bentley songs have consistently alternated between rowdy party anthems and deeply sensual slow jams. Few artists can pull off both with such proficiency.

He's been nothing if not an original since debuting in 2003. 'What Was I Thinkin'' was his debut single, and it became one of the most-played songs of the decade. However, he followed that up with 21 more No. 1 hits, so there is stiff competition for the top spot on this Top 20 Dierks Bentley Songs list.

  • 20

    "High Note"

    From 'Gravel & Gold' (2023)

    Dierks Bentley certainly hit a “high note” with his collaboration with acclaimed musician, Billy Strings. The twangy upbeat tune features plenty of banjo, fiddle and steel guitar, and is guaranteed to put a smile on the faces of both traditionalists and fans of Bentley’s 2010 Bluegrass album, Up on the Ridge.

  • 19

    "Every Mile a Memory"

    From 'Long Trip Alone' (2006)

    The lead single from Long Trip Alone, "Every Mile a Memory" has a mid-tempo production that effectively bolsters Bentley's scorching recount of his inner post-breakup turmoil. The song rose to become the then-newcomer's fourth No. 1 single on Billboard's Hot Country Songs chart in 2006.

  • 18

    "Heart of a Lonely Girl"

    From 'Home' (2012)

    Opening with lively fiddle lines, this Bluegrass tune finds Bentley ruminating, albeit breezily, on “the heart of [his] lonely girl.” It may have been too rootsy for commercial radio, but the track doesn't go unnoticed as one of Bentley's vibrant career standouts. While “Heart of a Lonely Girl” landed on 2012’s Home, it sure wouldn’t be a misfit on 2010’s Bluegrass-centered, Up on the Ridge.

  • 17

    "Am I the Only One"

    From 'Home' (2012)

    This was Bentley's comeback to country radio after the singles on his Bluegrass record, Up on the Ridge, received tepid airplay. Written by Bentley alongside hit songsmiths Jim Beavers and Jon Randall, the jubilant tune has a chorus that elicits loud singalongs at Bentley's live shows, especially on the almost-rowdy exclamation: “Am I the only one who wants to have a little fun tonight?!” Crank this one up for a guaranteed good time.

  • 16

    "Burning Man"

    From 'The Mountain' (2018)

    Has there been a more fiery, hard-hitting Dierks Bentley single than “Burning Man”? This chest-thumping, drum-heavy anthem narrates his contrasting desires to stay grounded while simultaneously living life wild and free. As Bentley proudly professes in the chorus: "I'm a little bit steady but still a little bit rolling stone.” Well, aren’t we all?

  • 15

    "Bad Angel"

    From 'Up on the Ridge' (2010)

    Bentley, Miranda Lambert, and Jamey Johnson strive to rid of their temptations, albeit in a light-hearted fashion, on this euphoric fiddle and mandolin-driven tune. While "Bad Angel" was never a single, the song got its due recognition at the 2011 Grammy's, where it earned a nomination for Best Country Collaboration with Vocals.

  • 14

    "Drunk on a Plane"

    From 'Riser' (2014)

    It's safe to say that "Drunk on a Plane" has become one of Bentley's most enduring singles. The upbeat, stadium-sized song features humorous lyrics that inject comedy into the normally depressing topic of breakups. Who’d have thought spending one’s post-breakup blues on a Boeing 767 would be this fun?

  • 13

    "Long Trip Alone"

    From 'Long Trip Alone' (2006)

    Maybe one could call Long Trip Alone Bentley's dark album, as the first two singles lacked the upbeat traveling rhythm for which he'd become known. This song about asking a girl to take him back was only a Top 10 hit, but it has maintained a place on country radio better than some of his other ballads. "So maybe you could walk with me a while / And maybe I could rest beneath your smile," he sings. Simple lyrics, yet from Bentley's lips, there's so much more unspoken.

  • 12

    "Woman, Amen"

    From 'The Mountain' (2018)

    The anthemic “Woman, Amen” reflects Bentley’s immense gratitude for his wife, Cassidy, and the indispensable role she plays in his life. “She gives me faith / She gives me grace / She gives me hope / She gives me strength / She gives me love / Love without end / Thank God for this woman, Amen,” he sings over an almost-cathartic upbeat production with “oh’s” perfect for a soaring live show singalong.

  • 11

    "How Am I Doin'"

    From 'Dierks Bentley' (2003)

    There are few better revenge songs that Bentley's hit from his 2003 self-titled album. What makes it wonderful is that the music absolutely matches the message. It's fun and unforgiving. "Well I don't know what you were thinking / Running 'round on me / Well now you say you're sorry ... well honey I agree," he sings just before the final chorus. This Dierks Bentley song is a cathartic slap to the face to any lover who has spurned you.

  • 10


    From 'Feel That Fire' (2009)

    The second single off Bentley’s Feel That Fire, this euphoric banjo and electric guitar-driven tune is equal parts upbeat and breezy. Imagine this: You’re unwinding after a long week of work at a bar with your friends and an attractive woman catches your eye. What unfolds next is gleefully narrated in “Sideways.”

  • 9


    From 'Riser' (2014)

    While it's nowhere near his biggest radio hit, "Riser" had to make the Top 10 Dierks Bentley Songs list. The title track of his seventh studio album is an inspirational track about the power of perseverance in the face of all odds, and its powerful message reached out to fans everywhere, offering solace and hope no matter what they were going through.

  • 8

    "I Hold On"

    From 'Riser' (2014)

    "I Hold On" perfectly captures the real-life experiences that form the foundation of country music. Composed by Bentley and Brett James, this sentimental ode features diaristic lyrics that are both personal and universal at the same time. Here, Bentley considers the significant things in his life that have anchored him to be the man he is today. “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,’ Bentley proclaims with grit in the chorus.

  • 7

    "Lot of Leavin' Left to Do"

    From 'Modern Day Drifter' (2005)

    Few artists are as influenced by their producer as Bentley is by Brett Beavers. Together, they've been enormously successful crafting a sound that borrows from Bakersfield, but adds a whole lot of heart. For the first time, fans got an idea of how important bluegrass music is on this No. 1 hit and the Modern Day Drifter album. He'd go on to include more and more pickin' and grinnin' before releasing an entire bluegrass album in 2010.

  • 6

    "I Wanna Make You Close Your Eyes"

    From 'Feel That Fire' (2009)

    Bentley was well on his way to becoming a heartthrob before this 2009 Top 5 hit. It's a simple love song about falling into a woman's arms after a long day and then seeing where it goes from there. "You can make me work for it girl if you want to / Just leave a trail for me to follow you into the bedroom," he sings. While Bentley might not be your typical country hunk, he sure sings that way in this song.

  • 5


    From 'Home' (2012)

    "5-1-5-0," the chart-topping Gold single from 2012 helped make Home a big success. This track went back to the sound that made Bentley famous and cleverly used the police code for a mentally unstable person in the title and chorus. Somehow, nobody was offended -- the song must be too catchy.

  • 4

    "Free and Easy (Down the Road I Go)"

    From 'Long Trip Alone' (2006)

    After four straight ballads, Bentley fans were ready to have fun again -- and they did during the summer of 2007 with this Top 5 hit. While this isn't the song that fans most identify Bentley with, it may be the one he seems most comfortable singing. The lyrics seem to fit his personality. "I could make a million or wind up broke / Free and easy down the road I go / Can't take it with you when you go so / Free and easy down the road I go," he sings. It's a great life philosophy.

  • 3


    From 'Home' (2012)

    Song and Single of the Year nominations helped secure"'Home" a place on the Top 10 Dierks Bentley Songs list. The album was Bentley's first since releasing a bluegrass project, and this single didn't exactly go right back to where he was before that diversion. Instead it mixed a few themes (pride, patriotism), creating a new style for the singer that he's built upon in future releases. "Home" was a No. 1 Gold single in 2012.

  • 2

    "Come a Little Closer"

    From 'Modern Day Drifter' (2005)

    The second single from Modern Day Drifter found Bentley pouring on the romance a la Conway Twitty. Few women could resist the sultry message of this song. It was a surprising change of pace for a man who until then had mostly been about uptempo bluegrass inspired rockers. "Come a little closer baby / I feel like layin' you down / On a bed of sweet surrender / Where we can work it all out," he sings with poetic confidence to open the track, one of the top Dierks Bentley songs. "Come a Little Closer" is one of two of his singles to go Gold.

  • 1

    "What Was I Thinkin'"

    From 'Dierks Bentley' (2003)

    Few songs from a debut artist succeed in changing the sound of the radio quite like Bentley's "What Was I Thinkin'" did. It was a song you waited around for and turned up to 11 when it finally played. The "little white tank top" lyric created a costume for his fanbase who still shout every word to this song when the singer plays it live. The No. 1 hit was also his first to go Gold with over 500,000 singles sold, but it gets the top spot on this Top 10 Dierks Bentley Songs list for the fever it created in the summer of 2003.

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