Since the release of their debut album Pawn Shop in 2015, Brothers Osborne have quickly become one of the biggest duos in country music history. The Deale, Maryland natives played music from a young age, performing alongside their siblings and other family members. John Osborne headed out to Nashville to attend Belmont University, and younger brother T.J. eventually followed, although they both initially tried to pursue their own solo careers. The pair decided to join forces and soon earned the interest of industry leaders and labels around town.

Brothers Osborne first made it onto the charts with their debut single "Let's Go There," which was followed by the infectious "Rum." Their third single "Stay a Little Longer" skyrocketed them to a new level of fame and began a streak of successful releases, including their 2016 single "21 Summer" and 2017's "It Ain't My Fault." The duo scooped up an array of industry awards, including Vocal Duo of the Year at both the CMA Awards and the ACM Awards.

Their success has continued to grow through two more album releases, 2018's Port Saint Joe and 2020's Skeletons, which they re-released as an extended edition in 2022. Along with their stellar work as a solo duo, John and T.J. have also recorded an array of stand out collaborations with some of country music's biggest names.

Here are The Boot's picks for the best Brothers Osborne collaborations, so far:

  • 10

    "In the Sweet By and By"

    with Leslie Jordan

    Actor and singer Leslie Jordan teamed up for TJ Osborne a version of "In the Sweet By and By," which was recorded for Leslie's 2021 debut album Company’s Comin’. Fun fact: Jordan also makes a guest appearance in Brothers Osborne's music video for "I’m Not For Everyone."

  • 9

    "Better With a Broken Heart"

    with Jillian Jacqueline
  • 8

    "I Smoke Weed"

    with Hardy and Ashland Craft

    This heady collaboration was recorded for the recently released HIXTAPE: Vol. 2, a collaborative record from Hardy, featuring 33 country artists on 14 tracks.

  • 7

    "Good at Tonight"

    with David Nail

    Co-written by Brothers Osborne, Troy Verges and Barry Dean, "Good at Tonight" was recorded for David Nail's fourth studio album Fighter. Released in 2016, the song served as one of the first major mainstream collaborations for the duo.

  • 6

    "Midnight Rider"

    with Dierks Bentley and Miranda Lambert
  • 5

    "Loving Me Back"

    with Lee Ann Womack

    A track from the duo's 2016 debut record Pawn Shop, "Loving Me Back" is an aching ballad anchored by traditional country imagery, from dive bars to bottles of Jack. Lee Ann Womack's stunning vocals bring the track to a new level, supplying one of the best tunes on an already stellar LP.

  • 4

    "Hard Workin' Man"

    with Brooks & Dunn

    When Brooks & Dunn decided to make a collaborative album with new versions of some of their biggest hits, they had a huge pool of talent to pull from. They recruited Brothers Osborne to put a new spin on their rollicking 1993 hit "Hard Workin' Man" for their all-star record Reboot in 2019.

  • 3

    "These Boots are Made for Walkin'"

    with Brittney Spencer

    Brothers Osborne teamed up with burgeoning country artist Brittney Spencer for a show-stopping cover of "These Boots are Made for Walkin'," made famous by Nancy Sinatra in 1966. The trio's fiery performance closed out the 2022 ACM Awards in style and provided one of the best live appearances of the broadcast.

  • 2

    "Burning Man"

    with Dierks Bentley

    Penned by Bobby Pinson and Luke Dick, "Burning Man" was released as the second single from Dierks Bentley's 2019 record The Mountain. Featuring TJ's captivating vocals and John's mind-blowing electric guitar solo to close things out, it's no wonder that the song made it all the way to No. 2 on the Billboard Country Airplay charts.

  • 1

    "All My Favorite People"

    with Maren Morris

    This track from Maren Morris' hit 2019 album Girl is a fun, anthemic collaboration tailor made for a late night sing-along. Morris has been close friends and creative collaborators with the Osborne brothers for many years, so it's no surprise that friendship is the core theme of this stand out tune.