Born in Oil City, Pennsylvania, Jackson studied at Virginia State University for one year, taking harmonica lessons before dropping out and playing guitar in a band.

They returned to compose the score for the downloadable content campaign Undead Nightmare in 2010, and Jackson provided additional in-game music for L.A. Noire in 2011.

[4] Jackson attended William Penn High School,[5] at which he was an honors student in his final year in 1988,[6][7] and studied at Virginia State University for one year,[8] where he took harmonica lessons, before transferring to study under Ellis Marsalis Jr.[4] He eventually dropped out when his funds were depleted, and turned to playing guitar with the blues band the Useless Playboys, often performing as the opening act for the Reverend Horton Heat.

[4] He performed in the group Hotel X, which released its album Engendered Species with SST Records in 1994; he also toured with the Useless Playboys around this time, alongside Mike Geier.

[8] Shortly after finding a German guitar in Los Angeles with the appropriate sound and "a perfect tremolo", Jackson returned home and wrote the game's main theme.

[29] Jackson and Elm returned to compose the score for Undead Nightmare (2010), a downloadable content campaign for Red Dead Redemption.

[17] Jayson Napolitano of Original Sound Version described Jackson's song as "a contemplative, lumbering piece of music that says a lot with few notes".

[37] In 2012, Jackson provided songs for Good Vibrations[38] and ModNation Racers: Road Trip[39] and additional music for the first season of Nashville with T Bone Burnett.

[41][42] Jackson released an original album, Dos Manos, in Italy in July 2012, produced by Holmes and published by Interbang Records and Brutture Moderne.

[47] Jackson's initial role was to provide the score for Trevor Philips's missions, and he took influence from artists such as The Mars Volta and Queens of the Stone Age.

[47] To compose his part of the score, Jackson created a supergroup called Jaws, featuring himself, Keefus Ciancia, Deantoni Parks, Gus Seyffert, and Michael Shuman.

[48] Alongside The Alchemist, Oh No, and Tangerine Dream, Jackson co-presented a 70-minute live concert featuring the game's original score at the New York Film Festival in September 2013.

[52] Ivan Pavlovich, director of music and audio at Rockstar, invited Jackson to work as the composer for Red Dead Redemption 2 (2018) around Grand Theft Auto V's release.

[54] He acquired a 1920s Gibson Mandobass used on Bullitt (1968) that recreated an "ominous" bell sound, ukuleles from Butch Cassidy and the Sundance Kid (1969), and a nylon guitar used on Unforgiven (1992).

[69] Jackson led an hour-long live performance of the soundtrack at the Red Bull Music Festival in Los Angeles in February 2019.

[71] On August 23, 2024, he released an instrumental album, Cowboy Yoga, performing alongside Jay Bellerose, Jennifer Condos, and Bill Frisell, and featuring guest appearances from Jackson's son Zach, Gabe Noel, Marc Ribot, and Sebastian Steinberg.