He is the chair of the bass department at Berklee College of Music.

[1] Bailey began playing bass guitar at age 12 and started playing fretless bass after he ran over his fretted Stuart Spector with his car.

He is a co-founder of Victor Wooten's Bass/Nature Camp, which helps to teach bassists of all ranges.

Bailey has worked with Ernestine Anderson, Bass Extremes, David Benoit, Tab Benoit, Michel Camilo, Larry Carlton, Paquito D'Rivera, Chris Duarte, Bryan Duncan, Brandon Fields, Dave Liebman, Dizzy Gillespie, Scott Henderson, Carol Kaye, Kitaro, T Lavitz, James Moody, Mark Murphy, Willie Nelson, John Patitucci, Ray Price, Toni Price, Emily Remler, The Rippingtons, Claudio Roditi, Billy Joe Shaver, Billy Sheehan, Lynyrd Skynyrd, Mel Tormé, and Jethro Tull.

His latest Album, CAROLINA, is a collection of 17 duets (one track of bass and another person doing what they do) featuring 17 different guests including Willie Nelson, Ian Anderson, Ron Carter, Victor Wooten, Mike Stern, Becca Stevens, Dennis Chambers and much more.