Dierks Bentley is a rare breed. He’s a chart-topper who fills arenas, sure, but he also took the time to release an entire bluegrass album in the middle of his red-hot career.
You recognize his voice the moment you hear it. And while he may not be the one to land huge vocal runs or shred guitars, he’s got an unmistakable style and a knack for writing some serious hits. Bentley manages to straddle that line between “light and fun” (with songs like “Somewhere On A Beach ” and “Am I The Only One”) and bona fide country gold tear jerkers.
Despite collaborations with artists like Jason Aldean, Cole Swindell and Blake Shelton, Bentley never really found himself dipping his toe into the bro country waters. He’s also collaborated with Miranda Lambert, Eric Church, Kenny Chesney, Brad Paisley, Carrie Underwood, Tim McGraw, Elle King, Alan Jackson and more. Even Kacey Musgraves and Chris Stapleton sang uncredited backup vocals on his albums for fun.
In other words, Dierks Bentley really transcends any one trend in country music and instead presents the full mainstream Nashville country package. So let’s take a look at the best Dierks Bentley songs, ranked.
10. “What Was I Thinkin'”
Dierks Bentley hit the jackpot on his first try with this tune. The first single from his first album in 2003, “What Was I Thinkin'” hit No. 1 on the charts. Bentley co-wrote the song with Deric Ruttan and Brett Beavers, both of whom became go-to collaborators for Bentley throughout the years. Beavers also produced several of Bentley’s albums throughout his career.
9. “Gonna Get There Someday”
Though it never got the single treatment, “Gonna Get There Someday” remains one of Bentley’s most heartfelt songs. Another Ruttan/Beavers collaboration, the song finds Bentley singing to another person about the personal changes he hopes to see within himself. By the end of the song, we realize he’s singing to his mother’s grave. It’s such a simple concept that is so wonderfully written.
8. “Come A Little Closer”
Another song from his album Modern Day Drifter, “Come A Little Closer” spent three non-consecutive weeks at No. 1 in 2005. It’s a slow and steady feel-good love song that is a crowd favorite to this day and is one of his most sensual and romantic songs.
7. “Draw Me A Map”
Though it didn’t find too much radio success, Bentley’s 2010 album Up On The Ridge is one of his most critically-acclaimed. Bringing in heavy doses of bluegrass influence, the album’s second single “Draw Me A Map” is the perfect example of Bentley’s ability to blend traditional influences with modern melodies. Who cares if this track didn’t chart very high on country airplay? It’s a darn good song.
This raucous tune is a reference to a California police code (5150) that allows authorities to involuntarily detain somebody who may be mentally ill or “crazy.” It’s a super clever idea that morphed into one of his fastest and more interesting songs. It’s just another reason Bentley’s concerts are so fun — nearly every song has a different vibe. And “5-1-5-0” is a heck of a changeup.
From his album of the same name, “Black” peaked at No. 2 on the Country Airplay charts, but that didn’t stop it from becoming one of his most popular songs off the new album. If “Come A Little Closer” is Bentley’s most sensual single, “Black” comes in at a close second. It also kicks off the whole record, which is a concept album done with tasteful references to his own marriage.
4. “Different For Girls”
As noted above, quite a few Dierks Bentley songs feature key guests. In “Different For Girls,” Bentley brings in a relative newcomer named Elle King. The alternative rocker adds a cool layer to this song about how guys and girls deal with breakups differently. The song notched Bentley his 13th Grammy nomination, although he’s still looking for a win.
3. “Say You Do”
On Bentley’s seventh studio album Riser, things really clicked. That might sound weird given the number of hits he already had up to that point, but this album took him from arena also-ran to arena headliner. “Say You Do” is one of the many standout tracks on the record. It became the album’s fourth single and his thirteenth overall No. 1
2. “Drunk On A Plane”
If you’re going to have to go with one of Bentley’s more light-hearted songs, why not go with the monster hit “Drunk On A Plane”? The song is one of his overall most successful tunes ever, and even merited its very own massive prop piece on his headlining tour. Both the sing-song chorus and its effect on Bentley’s career are undeniable.
1. “I Hold On”
But we couldn’t let that be the No. 1 overall song on the list. Instead, it’s this emotional burner of a single that showcases a little bit of everything that makes Bentley so great. It’s a very personal song for Bentley, detailing the stories behind his guitar, truck and the love of his life. Which is the other great point — it hits on all the classic country cliches without actually feeling cliche. That’s a tough task, and one Bentley pulls off masterfully on many songs, but none better than this one.