Hollingsworth purchased his first guitar at age 14, shortly after his father died. After starting and playing in a variety of bands including
Verbena and
The Dexateens, he began gaining notoriety in 2002 with the now-defunct Taylor and the Puffs. "Taylor and the Puffs" released Skybucket Records' first band recording ''You Know That Summer's Comin''' in 2003. In 2005, Hollingsworth released
Tragic City, a "gritty sludge-fest of a record," "recalling everyone from
Alice Cooper to
Dinosaur Jr. ... to
T. Rex and early
Tom Petty and the Heartbreakers." His next album,
Bad Little Kitty was released on July 29, 2008. The album was later nominated in the 8th Annual Independent Music Awards for "College Record Label Album of the year" in 2009. Hollingsworth was among several musicians, including Nik Freitas,
Jason Boesel, Macey Taylor, and
Nate Walcott to travel to
Tepoztlán, Mexico in 2007 to contribute to
Bright Eyes'
Conor Oberst's new solo recordings. that was rerecorded for the band's 2012 release
One of My Kind.
Life with a Slow Ear came out on Oberst's
Team Love Records label in November 2009. Paste called the album, which was recorded with
Andy LeMaster, "a scrappy, bare-bones production formed out of a love for honest, straightforward rock 'n roll." earning them praise as "the first couple of new Alabama music." As part of their best bands in all 50 states project,
Paste Magazine named them one of 12 bands you should know from
Alabama for tracks like "Ring Around Saturn" and "Hold on To" that "will bring to mind the collaboration between
John Prine and
Iris Dement." SDX (or "Sweet Dog Experience") is a two-piece consisting of Hollingsworth and Craig "Sweetdog" Pickering. They released
Pawn and Gun, recorded by
Memphis Punk Rock n' Roll Legend, Jack Oblivion in 2013 on
Team Love Records. Dead Fingers released their second album
Big Black Dog in 2014. The video for "Shoom Doom Babba Labba" premiered on
USA Today September 3, 2014. Hollingsworth rejoined
The Dexateens in 2015 opening for the
Drive-by Truckers and the
Alabama Shakes. Hollingsworth toured with
Conor Oberst throughout the U.S. and Europe playing in his backing band with members of
The Felice Brothers in support of Oberst's recent release,
Salutations. On May 11, 2017, they played Oberst's "Too Late to Fixate" on
The Late Late Show with James Corden featuring former
Beatles collaborator and
Traveling Wilburys drummer,
Jim Keltner on drums. The
Mystic Valley Band reunited for their first time since 2010 for a one-off New Year's Eve show at the Lodge Room in Highland Park, on December 31, 2017. In mid 2018, they announced a 7-date reunion tour through California and Arizona, with special guest
Phoebe Bridgers. In January 2019,
Conor Oberst and
Phoebe Bridgers released
Better Oblivion Community Center's debut studio album featuring only one non-Bridgers-Oberst composition, a cover of Hollingsworth's song "Dominos" from his album "Where To Go, How To Get There, And What You Should Know In Advance." In June 2019,
Paste Magazine premiered a new single from Hollingsworth entitled, "Devil N Me," from his new full-length record ''Tap Dancin' Daddy,'' out on Flower Moon Records called, calling it "the sound of the blues in 2019."
PopMatters premiered the titled track in July, saying it "calls to mind a '70s solo record from former
Rolling Stone Bill Wyman or the country colors of
Ronnie Lane's Slim Chance." Hollingsworth supported
Better Oblivion Community Center on tour in August 2019, as an opener and performing with the band on occasion during their final west coast tour. He is married to
Maria Taylor's sister, singer-songwriter Kate Taylor. Hollingsworth's photo, shot by
Robert M. Knight hangs on the front of a
Guitar Center in
Jackson, Mississippi, and Florida. ==Artistry==