Within a few years Deasy and his band, Shiloh, outscored Rusted Root to win the 1991 Graffiti Rock Challenge, a local Pittsburgh competition.

[1] By the mid-90s, with Shiloh defunct, a new group emerged and Deasy became the lead singer-songwriter of The Gathering Field, whose regional hit "Lost in America", from an album by the same name, led to a deal with Atlantic Records in 1996.

The majority of the new CD was recorded in Woodstock and New York City and features guitar work from The Clarks’ Rob James and producer Kevin Salem.

Recorded in Pittsburgh, it features members of the Bill Deasy band and a guest appearance by Los Angeles singer-songwriter Renee Stahl.

In November 2008 Deasy released A Different Kind of Wild, a collection of "heartfelt and earnest" songs that include him playing keyboards for the first time.

"[12] In 2013 Deasy released Start Again, a record that he says is a reflection of the musicians who first inspired him such as Van Morrison, Neil Young, Bob Dylan and Jackson Browne.

[13] Although Deasy pens the majority of his own material by himself, some collaborations do appear on the full-length CDs cited in this discography and the Gathering Field's Reliance album.

Some of these songs have appeared on albums by Martina McBride, Kim Richey, The Clarks, Bijou Phillips, Howard Jones, Billy Ray Cyrus and Michael Stanley.

He has written with songwriters such as Mark Hudson, Darrell Brown, Richie Supa, Stephen Bishop, Maia Sharp, Kim Richey, Jane Wiedlin and Jamie Houston.

Bill Deasy's debut, Ransom Seaborn, has an original premise, one amazingly eccentric character and some solid writing to recommend.

[6] – Deasy tours across the country as a headlining act but has also opened up for artists such as Bruce Springsteen, Bob Dylan, Rosanne Cash, Patty Griffin, John Hiatt, World Party, Norah Jones and the late Warren Zevon.