Dierks Bentley is a rare breed. He's a chart-topping singer-songwriter who fills arenas, sure, but he also took the time to release an entire bluegrass album in the middle of his red-hot career.
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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 such as "Somewhere On a Beach," "Sideways," "Lot of Leavin' Left to Do," "Am I the Only One" and "What the Hell Did I Say") and bona fide country gold tear-jerkers ("Settle for a Slowdown," "Long Trip Alone," "My Last Name"). He's won over fans with his more-introspective hits ("Every Mile a Memory," "Riser") and steamier love songs ("Feel That Fire," "Pick Up," "Pretty Girls," "I Wanna Make You Close Your Eyes").
Despite collaborations with artists such as 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, Patty Griffin, Maren Morris 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 dive into his 25 best songs.
Richard Gabriel Ford/Getty Images Dierks Bentley's overall lack of "bro-country" party anthems seems more like a professional choice than a creative deficiency when revisiting his guest appearance on this rocking pop-country banger by Cole Swindell. Rick Diamond/Getty Images for Kicker Country Stampede Not that Bentley hasn't flown solo as a party song-singing "bro." This one follows some of the tropes while bringing a Brad Paisley-like sense of self-awareness. Jason Kempin/Getty Images for "BRELAND & Friends" A carefree and fun summertime jam, "Beers on Me" is a superstar collaboration that sounds ready-made for an advertising campaign. The three collaborators share songwriting credits with Ashley Gorley, Luke Dick, Nicolle Galyon, Ross Copperman and Niko Moon. Christopher Polk/Getty Images for ACM On the folksier side of things, Bentley sang this song about romantic rendezvous with fellow superstar Maren Morris. Morris' now-ex husband, Ryan Hurd, was among the song's writers (along with Matt Dragstrem and Heather Morgan). Courtney Culbreath/Getty Images A bluegrasser at heart, Bentley covered one of U2's most meaningful classic rock radio staples — a tribute to Martin Luther King Jr. — with not just white-hot band the Punch Brothers but also one of bluegrass' living legends in Del McCoury. Michael Buckner/Getty Images As you should expect from a student of both bluegrass and country music, Bentley excelled when co-writing and recording a religious tune about the sweet by-and-by. Evan Frost/NHLI via Getty Images Bentley was at his smoothest as a country Casanova on this steamy love song. Seriously, it's got lyrics that'd make Conway Twitty blush. Brett Carlsen/Getty Images A great example of Bentley's willingness to change with the times, the folksy undercurrents here owe more to bearded indie rockers than clean-cut bluegrass band leaders. Terry Wyatt/ACMA2021/Getty Images Bentley's most recent radio hit (as of January 2024) makes him sound more like a twangy rockstar than ever before. Here, he more than holds his own against the stadium-filling country stars of the moment. Terry Wyatt/Getty Images for CMA At a time when country stars are digging deeper to the genre's roots, Bentley grabbed a shovel and teamed with Ashley McBryde. Together, they mythologize a trusty pair of cowboy boots, considering what a given pair's walked through in their owner's life. Terry Wyatt/Getty Image Though it never got the single treatment, "Gonna Get There Someday" remains one of Bentley's most heartfelt songs. Another Deric Ruttan/Brett 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. Scott Legato/Getty Images Bentley takes a few pages from Kenny Chesney's playbook on this sentimental story-song. It was a '90s country throwback before '90s country throwbacks became cool. Mike Coppola/Getty Images for CMT A collaboration with sensational country music duo Brothers Osborne, "Burning Man" was released in May 2018 as the second single off The Mountain. TJ Osborne provided guest vocals while John Osborne played lead guitar for the single. The song peaked on Billboard's Hot Country Songs chart at No. 5 and reached No. 2 on country radio. Adam Glanzman/Getty Images "Living" was released in February 2019 as Bentley's third single off his 2018 album, The Mountain. The song was co-written by the country singer, Ashley Gorley, Jon Nite and Ross Copperman. The song, which went platinum, reached No. 1 on Billboard's Country Airplay chart. Fun fact: The official music video for the song featured Bentley's son, Knox, who was 5 years old at the time. R. Diamond/WireImage Bentley hit the jackpot on his first try with this tune. His debut single "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 has also produced several of Bentley's albums. Ed Rode/WireImage 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 easily his most sensual and romantic song. John Shearer/Getty Images for ACM 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. Christopher Polk/ACA2012/Getty Images This song's title is a reference to a California police code (5150) and 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. Mike Coppola/Getty Images 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 project, which is a concept album done with tasteful references to his own marriage. Michael Hurcomb/Corbis via Getty Images 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 13th overall No. 1. Douglas Mason/Getty Images Bentley closed his most recent album — and scored his most recent Grammy nomination as of 2024 — with a hilarious take on the apocalypse with help from fellow bluegrass devotee Billy Strings. It's got it all: great picking, great singing and great lyrical zingers. Rick Diamond/Getty Images for Country Music Hall of Fame Only Keith Urban can approach Bentley when it comes to mixing pop-friendly songwriting with rock and traditional country instrumentation. Crushing guitar riffs and banjo accompaniment propel what otherwise might be a run-of-the-mill song about an evening on the dance floor. Rick Diamond/WireImage This platinum-certified No. 1 hit brought steel guitar back to the radio. Beyond that classic country element, there are ample doses of bluegrass proficiency and country-rock drive. Kevin Winter/ACMA2014/Getty Images for ACM 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"? It's 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. Rick Diamond/Getty Images 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."Flatliner" (With Cole Swindell) (Swindell's You Should Be Here, 2016)
"Somewhere on a Beach" (Black, 2016)
"Beers on Me" (Feat. Breland and Hardy) (Single, 2021)
"I'll Be the Moon" (Feat. Maren Morris) (Black, 2016)
"Pride (In the Name of Love)" (Feat. Del McCoury and the Punch Brothers) (Up On The Ridge, 2010)
"The Heaven I'm Headed To" (Long Trip Alone, 2006)
"I Wanna Make You Close Your Eyes" (Feel That Fire, 2009)
"Woman, Amen" (The Mountain, 2018)
"Gold" (Gravel & Gold, 2023)
"Cowboy Boots" (Feat. Ashley McBryde) (Gravel & Gold, 2023)
"Gonna Get There Someday" (Modern Day Drifter, 2005)
"Every Mile a Memory," Dierks Bentley (Long Trip Alone, 2006)
"Burning Man" (Feat. Brothers Osborne) (The Mountain, 2018)
"Living" (The Mountain, 2018)
"What Was I Thinkin'" (Dierks Bentley, 2003)
"Come a Little Closer" (Modern Day Drifter, 2005)
"Draw Me a Map" (Up On the Ridge, 2016)
"5-1-5-0" (Home, 2012)
"Black" (Black, 2016)
"Say You Do" (Riser, 2014)
"High Note" (Feat. Billy Strings) (Gravel & Gold, 2023)
"Sideways" (Feel That Fire, 2009)
"Free and Easy (Down the Road I Go)" (Long Trip Alone, 2006)
"Drunk On a Plane" (Riser, 2014)
"I Hold On" (Riser, 2014)
Editor's Note: This story originally ran on Nov. 20, 2018. It was updated on Jan. 26, 2024.
