In 1996 LaFave received the Kerrville Folk Festival songwriter of the year award and appeared on the TV show Austin City Limits.

[1] LaFave was inducted into the Oklahoma Music Hall of Fame in 2017 alongside Carl Belew, musician-actor Rodney Lay, the Red Dirt Rangers, David Teegarden, Sr. and singer-harmonica player Junior Markham.

[1] At age 15 LaFave switched to guitar and began writing and singing his own songs in a band called The Night Tribe.

Later, in 1988, LaFave self-released a cassette only album "Highway Angels... Full Moon Rain", which featured his photography as the cover artwork.

While living in Stillwater, LaFave and a loose collection of songwriters at a local venue known as "the farm" began developing a sound that would later become known as "red dirt music".

[4] Mixing blues, jazz, and country influences he began writing songs inspired by[3] J. J. Cale, Chet Baker, Bob Dylan and Leon Russell.

Between 1997 and 2001, LaFave released three more albums on the label including the 1999 double CD Trail, which was a 15-year retrospective of live performances and studio outtakes.

[10] LaFave gained nationwide exposure in 1996 through his appearance on the PBS music show Austin City Limits when he was paired with Lisa Loeb for an evening of "acoustic ballads and electrified folk-rock numbers".

[15] LaFave's "red dirt music" sound has been described as a mix of rock, folk, rockabilly, and country, grounded in the landscape of Texas and Oklahoma and can be heard on this album.

[1] LaFave left Bohemia Beat for Red House Records and released his 2005 album Blue Nightfall which one reviewer called his "best work yet" and "a great introduction to an important artist".

In her review for The Oklahoman, Brandy McDonnell said: "Jimmy LaFave’s first studio album in five years, lives up to the intriguing promise of its title, finding the Oklahoma-Texas troubadour in a contemplative mood whether he is crooning his new original songs, covering an ’80s pop smash or reinterpreting anthems penned by Rock and Roll Hall of Famers Bob Dylan and Bruce Springsteen.

The album features Bruce Springsteen, Lyle Lovett, Bonnie Raitt, Ben Harper, Keb Mo', Shawn Colvin, Lucinda Williams, and others.

[33] In an article published in The Austin Chronicle in April 2017, LaFave announced publicly that he was battling myxofibrosarcoma,[34] a rare form of cancer that had been diagnosed one year earlier.

According to The Austin Statesman: "A sold-out audience heard artists ranging from Austin artists including Eliza Gilkyson, Slaid Cleaves and Ruthie Foster, plus some from out-of-state including Nashville’s Gretchen Peters, Boston’s Ellis Paul and Woody Guthrie’s granddaughter Sarah Lee Guthrie, primarily playing songs that LaFave wrote or were part of his repertoire.

"[38] Within 24 hours, LaFave's death was reported in numerous newspapers throughout Texas and Oklahoma, in The New York Times[37] and as far away as England and The Netherlands, where he often performed.