The duo have since had further hits with "It Ain't My Fault" (2017), "Shoot Me Straight" (2018), and "All Night" (2019), and as featured artists on Dierks Bentley's "Burning Man" (2019).

Artists with whom they have worked include David Nail, Lee Ann Womack, and Lucie Silvas (the latter of whom is John's wife).

Together, they played in a band called Deuces and a Quarter, while also helping their father with his day job as a plumber.

"[3] It reached a similar Billboard chart position, which continued to halt an official album release from EMI.

"[10] Hannah Smith of Vinyl magazine praised the project and anticipated future success for the pair: "Brothers Osborne is a duo who are redefining the lines and following in the footsteps of trailblazers who have launched a revolution with their distinct music.

[16][17] Pawn Shop received four stars from Allmusic's Stephen Thomas Erlewine who called it "busy, but never overstuffed.

"[19] Two additional singles were spawned following the record's release that later became hits: "21 Summer" and "It Ain't My Fault.

[4] Also in 2016, the brothers co-wrote and sang on the track "Good at Tonight" on David Nail's album Fighter.

[21] In early 2018, the brothers announced the release of their second studio record titled Port Saint Joe.

"[27] Allmusic's Stephen Thomas Erlewine called it a "clever, smart, adventurous, and hooky, creating a slow-rolling good-time vibe that doesn't lose its luster with repeated plays.

[31] They also joined Brooks & Dunn on their 2019 album Reboot, where they contributed to a re-recording of that duo's 1993 hit "Hard Workin' Man".

[33] In spring of 2019 The Brothers Osborne were featured guests on the PBS concert series Bluegrass Underground (now re-branded as The Caverns Sessions).

Also produced by Jay Joyce, the album included songs written by the brothers, with several Nashville songwriters.

"[38] Skeletons received a favorable response from Allmusic's Stephen Thomas Erlewine, who rated the project four and half stars.

[42] Brothers Osborne provided backing vocals to Ashley McBryde's 2022 album Lindeville, on which John also served as producer.

[48] John Osborne is the main instrumentalist of the group, playing primarily electric guitar, while TJ is the lead vocalist.

Of their sound, Spin writer Andrew Unterberger said, "John's guitar slides a Hattori Hanzō sharpness, while TJ’s vocals are wisely kept from going too thick with warbling vibrato, allowing them an understated vulnerability badly lacking in Nashville these days.

"[49] Stephen Thomas Erlewine contrasted the duo with Sam Hunt and Chris Stapleton, saying that they have "the modern rhythmic snap of the former and the classicist structure of the latter.

He also compared TJ's "sonorous, ultra-deep voice" favorably to Trace Adkins and noting the variety of guitar styles played by John as "sometimes steely, sometimes twangy, sometimes rocking".

[51] When asked to name the ten albums that were the biggest influences on his musical life, John Osborne selected releases by Darrell Scott, Patty Loveless, Lucinda Williams, Merle Haggard, Willie Nelson, Alan Jackson, Dwight Yoakam, The Chicks, Alison Krauss & Union Station, and Lee Ann Womack.

[53] That same year, John played guitar on and co-produced Silvas' studio album Letters to Ghosts.