The Boulware family moved to Charlotte, North Carolina then Atlanta, Georgia where Will started playing the piano at age five. Will’s father played the guitar and sang cowboy songs along with his mother, Alberta Boulware Connelly, who still sings quite well.

At age 10, Will bought a set of drums and formed his first group Wee Willy & The Winks in which he played drums doing surf music until 13 when he traded in the drums for his first electric keyboard and started to listen to Jimmy Smith and his father's Erroll Garner and Dave Brubeck records. When he was fourteen, he was already in an R&B group performing. He also played the organ in a trio he formed and started performing his own compositions. By 1972, his songs were recorded by B.B. King. At 21 Will moved to New York City where he mainly worked doing recording sessions in commercial field.

In the 1980s, Boulware lived in California doing some solo piano gigs and working with guitarists such as Scott Henderson, Phil Upchurch and Ron Eschete. By 1990, Boulware moved back to NYC where he started working with the late Phyllis Hyman. He also started in 1993 a 10-year organ stint with saxophonist Maceo Parker and touring with The Blues Brothers (1998), John Scofield (1999) and Carla Bley (2000). He also performed on Rodney Jones recordings and others.