Born and raised in Kentucky, as a teen he joined his parents and five of his siblings in the chart-topping gospel group the Crabb Family from 1995 until 2007, when they went on hiatus to pursue individual projects. Crabb released his first solo album, Jason Crabb, on Spring Hill Music Group in 2009. It peaked at number 62 on the Billboard 200 and went on to win a Grammy for Best Southern/Country/Bluegrass Album in 2010. He followed it up with a seasonal record, Because It's Christmas, later in 2010. In 2011 he released a live album and concert DVD titled The Song Lives On, and the Crabb Family reunited for a tour that same year, followed by the 2012 studio album Together Again, produced by Crabb. Another solo album, Love Is Stronger, arrived in 2013 on the Gaither Music Group label. Also a frequent collaborator with other gospel artists, he appeared on albums including Brooklyn Tabernacle Choir's I'm Amazed…LIVE (2005), Gaither Vocal Band's Better Day (2010), and Kirk Cameron's Saving Christmas soundtrack (2014), among many others, as well as on several Gaither Homecoming home video releases.
In March 2015, he released his first solo compilation, Through the Fire: The Best of Jason Crabb. It was followed that September by his fourth studio album, Whatever the Road, his first with Provident Label Group. In 2018, he issued the full-length Unexpected, which featured contributions by Rascal Flatts' Gary LeVox and former Pussycat Doll Kaya Jones. It won him the Grammy for Best Roots Gospel Album the following year. The year 2020 brought the Crabb Family release 20/20. More than a decade had passed since Crabb's last Christmas LP by the time he delivered Miracle in a Manger in October 2022. Its production team included Tim Akers, Kevin Rooney, and Rascal Flatts' Jay DeMarcus. ~ Marcy Donelson, Rovi