Born in Kentucky, Cowherd was introduced to music at a young age by his parents, who were both musicians and teachers. Along with studying the piano, he sang and played French horn and violin. After high school, he attended Loyola University in New Orleans where he studied jazz improvisation with luminaries like Ellis Marsalis and John Mahoney. It was also during this period that he befriended drummer Brian Blade, with whom he co-founded the Brian Blade Fellowship, appearing on the group's acclaimed 1998 debut, as well as 2000's Perceptual, 2008's Season of Change, and 2014's Grammy-nominated Landmarks.
As a leader, Cowherd debuted with 2013's Mercy, featuring his group with Blade, bassist John Patitucci, and guitarist Bill Frisell. The pianist has also worked with a bevy of highly regarded artists from across the musical spectrum, including Lizz Wright, Myron Walden, Iggy Pop, Glen Hansard, Brandi Carlile, John Scofield, and Rosanne Cash, to name a few. In 2017, he was back with the Fellowship for Body and Shadow. That same year, he released his sophomore album, Gateway, with Steve Cardenas and Tony Scherr. Pride Joy arrived in 2022 and featured his trio with Blade and Patitucci, along with saxophonist Chris Potter and percussionist Alex Acuña. ~ Matt Collar, Rovi