Jason Boland was born in Harrah, Oklahoma. Though his mother was originally from Arkansas, he still has family near Clinton, Oklahoma. Jason developed an early interest in music, drawing inspiration from the rock and roll and country singers of the 1950s. He attended local schools in Harrah and, after graduation, came close to joining the seminary. Instead, he chose to study business at Oklahoma State University in Stillwater, north of his hometown.
While attending Oklahoma State, Boland became a member of the Lambda Chi Alpha fraternity, where he met his future friend and bandmate, Brad Rice. Stillwater, widely regarded as the heart of the red dirt music scene, proved to be an influential environment in shaping his musical path.
In 1998, Jason Boland and his friends founded their band, Jason Boland & The Stragglers. Known for its fusion of red dirt country and honky-tonk traditions, the group quickly built a devoted fan base. Boland served as the lead vocalist and frontman.
The band's debut album, Pearl Snaps, was released in October 1999 and became a foundational piece of the red dirt scene. The album received critical acclaim for its authenticity and songwriting. In 2001, they followed up with their second studio album, Truckstop Diaries. A live recording, Live and Lit at Billy Bob's Texas, captured their energetic performance in Fort Worth in 2002 and further solidified their growing reputation.
In 2004, Boland released his third studio album, Somewhere in the Middle, which achieved notable success on the country charts. Reflecting on the band's evolution, Boland has said, “We pay homage, but we don't want to copy or be a throwback act. All you can do is try to take the music that inspires you and take it further. And make it personal.”
In October 2005, Boland briefly paused his career to enter the Sierra Tucson Treatment Center in Arizona, after experiencing severe alcohol withdrawal symptoms. Despite this setback, he continued writing music during his recovery. His comeback album in 2006, The Bourbon Legend, produced by longtime Dwight Yoakam collaborator Pete Anderson, marked an even stronger return to the charts.
In 2008, Boland suffered a vocal cord rupture during a performance. He later attributed it to “too much yelling and not enough singing.” After undergoing surgery and vocal therapy, he resumed performing. That same year, the band released Comal County Blue, which landed at No. 30 on the country charts and was praised for its introspective lyrics and distinctive sound.
Despite a near relentless touring schedule, the band continued producing material. From 2008 to 2010, they released two more studio albums and a live album, High in the Rockies: A Live Album, recorded during shows across Colorado and Wyoming. In 2010, they also released their first music video for the song “Tulsa Time.”
Their 2011 album, Rancho Alto, was co-produced with Shooter Jennings, a collaboration that continued with their 2013 album, Dark & Dirty Mile. In October 2015, they released Squelch, which was well received by both fans and critics.
| Net Worth 2021: | 20 million |
