Dierks Bentley is no stranger to collaborations in his over-a-decade-long career. Whether it’s on the commercial country fare or Bluegrass projects, Bentley isn’t afraid to explore the magic that brews when talented artists come together — and his catalog of duets proves that.

A Phoenix, Ariz., native, Bentley first launched on the scene in 2003 with his self-titled album. Right from the get-go, the singer issued a Bluegrass collaboration, “Train Travelin’,” with​​ the Del McCoury Band, alongside radio hits like “What Was I Thinkin’” and “How Am I Doin’.” The pair would reunite on Bentley’s follow-up record, Modern Day Drifter, which included “Come A Little Closer,” “Lot of Leavin’ Left to Do,” and their second duet, “Good Man Like Me.”

Subsequently, most albums that followed featured at least one collaboration, with artists such as Miranda Lambert, Jamey Johnson, Brandi Carlile, Hardy and the Grascals. Bentley also often showcases his deep love for bluegrass, as evidenced by his critically-acclaimed 2010 record, Up on the Ridge.

Now a bonafide country star and official Grand Ole Opry Member, Bentley boasts 21 No. 1 hits, 14 Grammy nominations, as well as multiple ACM, CMA and Billboard Music Awards nominations.

In celebration of Bentley’s new single and yet another hit-ready collaboration with Elle King, “Worth The Shot," The Boot looks back at Bentley’s past collaborations and ranking them from ten to 1. Find out if your favorites made the list!

  • 10


    with Cole Swindell

    Serving as the third single from Cole Swindell’s sophomore album You Should Be Here, this uptempo pop-country song finds the singers head over heels over a drop-dead gorgeous woman they just laid eyes on. The hook of the song is in the chorus - “She's a little heart stopper / I'm talkin' breaker breaker one-niner / She's a flatliner,” which is essentially what the story revolves around. While there’s not much lyrical depth here, its heart-racing upbeat production makes for a good live concert experience. This peaked at No. 2 on Billboard’s Country Airplay chart.

  • 9

    "Lay Here With Me"

    with Maddie & Tae

    For this 2020 cut, Maddie & Tae team up with their UMG Nashville labelmate to deliver a passionate ode. Featuring the delicate delivery of the “Girl in a Country Song” and Bentley’s signature gravely vocals, this romantic tune that will resonate with couples everywhere.

  • 8

    "Train Travelin'"

    with the Del McCoury Band

    Solely written by Bentley, this Bluegrass song features the Grammy-winning Del McCoury Band laying their signature traditional instrumentation as the then-country newcomer ponders on his life over rich lyrical imagery. This song was also the closing track of Bentley’s 2003 debut album with Capitol Nashville.

  • 7

    "Bottle to the Bottom"

    with Kris Kristofferson

    It's not every day that Kris Kristofferson green-lights another artist to cut a song he wrote and recorded, but managed got that honor with this song, which was featured on his 2010 bluegrass record, Up on the Ridge. This jaunty breakup tune was first made famous in 1969 by Billy Walker and the Tennessee Walkers, before the “Sunday Mornin’ Comin’ Down” singer released it in 1973 as a duet with Rita Coolidge. On Bentley’s rendition, Kristofferson trades turns with his fellow duet partner on the second verse, before providing light harmonies with Bentley in the chorus.

  • 6

    "Pride (In the Name of Love)"

    with Del McCoury and The Punch Brothers

    This 1984 cut from Irish rock band U2 received a very special Bluegrass treatment by Bentley in 2010 for Up on the Ridge. Enlisting the prowess of Del McCoury and the Punch Brothers, Bentley’s delightful banjo-driven rendition offers a fresh spin on an originally electrifying rock number.

  • 5

    "Different For Girls"

    with Elle King

    This 2016 cut was Elle King’s formal introduction to the country music format. The honestly-written song by J.T. Harding and Shane McAnally offers both a male and female perspective on breakups, as narrated by Bentley and King respectively. It became a No. 1 on Billboard’s Country Airplay charts and was King’s first-ever chart-topper in the country genre.

  • 4

    "Travelin' Light"

    Brandi Carlile

    It’s always refreshing when contemporary artists pay homage to the organic instrumentation of the past, and this is exactly what Bentley and Carlile do on their first-ever collaboration together. The breezy, vibrant Bluegrass track was co-written by Bentley with Ross Copperman, Jon Nite and Ashley Gorley and was one of two duets on 2018’s The Mountain.

  • 3

    "Burning Man"

    with Brothers Osborne

    This chest-thumping heater, complete with TJ Osborne’s baritone delivery, was written by famed songsmiths Luke Dick and Bobby Pinson and served as the second single off The Mountain. Its singalong hook, “I'm a little bit holy water but still a little bit burning man,” makes it an anthem for all who trek their unique life voyage. The one peaked at No. 2 on the Billboard Country Airplay chart.

  • 2

    "The Driver"

    with Charles Kelley and Eric Paslay

    Bentley’s aching vocals take center stage on the bridge of this powerfully honest ballad which chronicles the joys and woes experienced by a driver, dreamer, and singer. It bellyaches the moments of hopelessness, while also offering encouragement and testimony of perseverance. Written by Charles Kelley, Eric Paslay and Abe Stoklasa, it served as the lead and title track of Kelley’s 2016 debut solo album.

  • 1

    "Bad Angel"

    with Miranda Lambert and Jamey Johnson

    This was a star-studded dream collaboration featuring three of the best visionaries and artists in country music. Here, Bentley taps on Miranda Lambert and Jamey Johnson to bring this bouncy banjo-driven ​​Verlon Thompson and Suzi Ragsdale-penned song to life. Of the joint effort, Bentley told The Boot in 2010, “I thought of two people who would be perfect on it, whose voices who would all complement each other. They were the first two names that came up, and it was really easy to get them on there. They're excited about it.”

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