The Kentucky-raised, New Orleans-schooled, New York-based Cowherd is best known for his long- running partnership with drummer/bandleader Brian Blade, with whom he co-founded the Grammy nominated Brian Blade and the Fellowship Band, whose acclaimed, influential albums showcase Cowherd's stellar keyboard work and singular compositional skills. When not recording and touring with the Fellowship, Cowherd has worked extensively with a broad array of players and singers from the jazz, pop and rock worlds including Joni Mitchell, Norah Jones, Brandi Carlile, KD Lang, Rosanne Cash, Iggy Pop, Glen Hansard, Cassandra Wilson, John Scofield and Lizz Wright.

In 2013, ArtistShare and Blue Note records released Cowherd’s first album as a leader “Mercy” which features Bill Frisell, John Patitucci and Brian Blade. Cowherd and Blade also directed the all star Joni Mitchell tribute “Joni 75” along with such artists as Brandi Carlile, Glen Hansard, Emmylou Harris, Norah Jones, Chaka Khan, Diana Krall, Kris Kristofferson, Los Lobos with Marisoul, Graham Nash, Seal, James Taylor and Rufus Wainwright.

In 2017 Cowherd released a new recording on the exclusive “vinyl only” Newvelle record label. “Gateway” consists of 7 compositions by Cowherd and one from Brian Blade and features Steve Cardenas and Tony Scherr.

As an arranger, Cowherd has scored for big band, strings and symphony orchestra for Brandi Carlile, Cassandra Wilson, Lizz Wright, the Fellowship Band and the Shreveport Symphony and the Loyola University Symphony Orchestra.

Other current touring projects include Alicia Olatuja, Nate Smith and Kinfolk, Tom Guarna’s Wishing Stones project and a new project with John Scofield touring in the Spring & Summer 2022 called “Yankee Go Home”.