Jason Boland & The Stragglers are an American Red Dirt/Texas Country band featuring Harrah, Oklahoma, native Jason Boland (lead vocalist and guitar), Roger Ray (steel guitar, lead/rhythm guitar), Brad Rice (percussion), Grant Tracy (bass), and Nick Worley (fiddle and mandolin).
Jason Boland and Brad Rice are both members of the Lambda Chi Alpha fraternity, having met in Stillwater, Oklahoma, while attending Oklahoma State University. Boland formed a band in 1998, releasing their first album, Pearl Snaps, in 1999. Boland and The Stragglers became one of the most successful artists in the Red Dirt/Texas Country scene. Studio albums Truckstop Diaries and Somewhere in the Middle followed in 2001 and 2004, respectively; a concert at Fort Worth, Texas, dancehall Billy Bob's Texas was recorded for Live and Lit at Billy Bob's Texas in 2002.
The Bourbon Legend was released on Bruce Robison's Sustain Records label in late 2006. It was produced by longtime Dwight Yoakam collaborator Pete Anderson.
In 2007, Jason Boland co-produced the album Choices for the band Hazzard. The band's front man, Dana Hazzard, was the original fiddle player for the Stragglers.
In 2008, just before the release of the album Comal County Blue, Boland ruptured a vocal cord. The injury almost caused him to lose his singing voice for good, but after surgery and resting his voice, he recovered.
According to Katie Key, editor of the Texas Music Chart, "Comal County Blue" was the fastest growing single in 2008 from an independent label. On April 20, 2010, the band released their second live album, entitled High in the Rockies: A Live Album. The recordings come from four live concerts over four days from January 7, 2010 to January 10, 2010. The shows were performed in Steamboat Springs, Colorado, Ft. Collins, Colorado, Laramie, Wyoming, and Denver, Colorado, respectively.
The band released Dark & Dirty Mile on May 14, 2013. Shooter Jennings (son of country music artist Waylon Jennings) co-produced the album with the band. The title track was a top-five single on the Texas Music chart in May 2013.
The band is currently based in Austin, Texas.