In 2007 Bailey was nominated for the Birmingham Area Music Awards in the category of best Country/Bluegrass/Americana artist. He also plays with Birmingham-based favorites such as Stuart McNair and the Contraband, Lolly Lee and Jason Bailey (a.k.a. Sugar Mama and the Poolboy), The Lost Jim Trio, Celtic-infused Shilleleagh Law, folk/rock jasonbailey_featured_WThree Man Stone, bluegrass group The Bluegrass Cartel and the regional touring jazz/ bluegrass/ southern jam band Tonal Vision. He has been a guest at Birmingham’s City Stages and Do Dah Day, Mobile’s Bayfest, Georgia’s Little Turnip Town Overnight Music Jam, and The Acoustic Café in Hayden, Alabama to name a few.

Jason Bailey has influences from the pioneers of acoustic music, such as David Grisman, Tony Rice, Stephanne Grappelli, Tim O’Brien, Sam Bush, Mike Marshall and many more. However, what sets Jason apart from others in this genre is that his music is yet another step further from the previously pushed boundaries of his predecessors.