His older sister Cari Jean (Jeannie's daughter by an earlier marriage) died suddenly at age 15 from complications after surgery.

[4] Bare grew up in Hendersonville, Tennessee, a half an hour northeast of Nashville, where his family lived next door to Tammy Wynette and George Jones.

He and his siblings also appeared on the television show Hee Haw when he was a child, to provide the witch scream on Bobby Bare, Sr.'s song "Marie Laveau".

[14] He has performed with his band, the Young Criminals Starvation League, an ever-changing group of musicians, including members of Lambchop, ...And You Will Know Us by the Trail of Dead, and My Morning Jacket.

[19] Bare recorded the album with Mark Nevers (Lambchop) and Grammy-winning engineer Vance Powell (Jack White, Alicia Keys, the Dixie Chicks, Buddy Guy).

[20] In February 2016, Bare joined a new touring lineup of Robert Pollard's band, Guided by Voices, as guitarist along with Doug Gillard also on guitar, bassist Mark Shue and drummer Kevin March.

[21][22] Bare played guitar on Guided by Voices albums August by Cake (2017), How Do You Spell Heaven (2017), Space Gun (2018), Zeppelin Over China (2019), Warp and Woof (2019), Sweating the Plague (2019), Surrender Your Poppy Fields (2020), Mirrored Aztec (2020), Styles We Paid For (2020), Earth Man Blues (2021), It's Not Them.

(2021), Crystal Nuns Cathedral (2022), Tremblers And Goggles By Rank (2022), La La Land (2023), and Welshpool Frillies (2023), as well as participating in two releases by a GBV alter-ego, Cub Scout Bowling Pins - Heaven Beats Iowa (2021) and Clang Clang Ho (2021) - as well as several releases by another alter-ego, Cash Rivers And The Sinners - She Laughed I left (2017), Blue Balls Lincoln (2018), Do Not Try To Adjust Your Set (2018 - featuring a cameo from Bobby Bare Sr), Loose Shoes (2019), and Bad Side Of The Coin (2020).

[26] Musicians appearing in the film include My Morning Jacket, Justin Townes Earle, Hayes Carll, David Vandervelde, Blue Giant, Duane Denison and Bobby Bare Sr.[27] The documentary was photographed on several formats, including Super 16mm, 16mm, Super 8, and HD[28] and had its East Coast premiere at the CBGB Film Festival[29] in October 2013.