He was a guitarist and singer in the Southeastern rock club band Baghdad in the mid-80s that played both covers and original work,[5] before moving to Nashville, Tennessee, in 1987.

He was a fan of Kiss and of Todd Rundgren, but mostly practiced Eddie Van Halen and Steve Morse licks note-for-note.

[citation needed] Nashville music executive Scott Siman encouraged Owsley to pursue his own writing and performing, which is why he declined an offer by Amy Grant in the late 1980s to become her guitarist.

[8] Amy Grant turned out to have heard tapes of The Semantics and she contacted Owsley in 1994 to let him know how much she liked it, and to ask him to join her as her guitarist on the House of Love tour.

[15] During the 1990s, he among others worked with Vince Gill,[14][15] Michael W. Smith,[14] Chris Rodriguez,[14] dc Talk[16] (for whom he also produced),[3] the Neville Brothers,[3] Vanessa L. Williams,[3] and Wynonna.

[citation needed] With the money he earned working with Amy Grant and Shania Twain, he bought a house in Green Hills, Tennessee, and in it built a home recording studio.

Doug Morris of Universal Music Group picked it and proposed the album to be rerecorded,[8] but Owsley insisted that it simply needed to be remixed by either Tom Lord-Alge, Bob Clearmountain or Andy Wallace.

[9] Recorded almost entirely on a vintage Studer A-80 (2-inch, 16-track of which one defective[19]) tape machine[20] in his home studio on Hobbs Road in Nashville, Tennessee, it garnered him a Grammy Award nomination for Best Engineered Album.

[21] During the ensuing tour, he among others joined the Pat McGee Band[3] and Fountains of Wayne,[22] whose bassist Adam Schlesinger Owsley recorded with in later years.

[13] A cover of Paul McCartney's "Band on the Run", which Owsley recorded for a 2001 tribute album,[25] was included as a hidden track.

That same year, Owsley contributed the cover song "Got a Lot on My Head" to Substitution Mass Confusion, a tribute album in honor of The Cars.

[27] In the 2000s (decade), Owsley continued work as a session guitarist, (backing) vocalist, mandolin player and less frequently as bassist and keyboardist.

He among others recorded with Faith Hill,[7][15] Michael McDonald,[15] Charlotte Church,[14][15] Jump5,[14] Natalie Grant,[14] David Phelps,[14] James Ingram,[14] Rodney Crowell,[14] MercyMe,[14] The Katinas,[14] Nate Sallie,[14] Graham Colton,[14] and Kenny Loggins.

[14] Producer John Fields arranged for Owsley to back various Disney stars, such as Miley Cyrus,[15] Selena Gomez,[15] Demi Lovato,[15] the Jonas Brothers,[14][15] and Luke Benward.

[29] In the last two years of his life, Owsley occasionally worked as a session guitarist for Andy Sturmer's movie soundtracks.

[32] In 2011, Vince Gill released the song "Threaten Me With Heaven", which was co-written with Amy Grant, Owsley and Dillon O'Brian.

It was nominated for the 2012 Grammy Awards in the category of "Best Country Song",[2] which according to Gill is "a lasting tribute to Owsley" and "would have meant the world to him".