Vassar made his debut on the country music scene in the late 1990's co-writing singles for several country artists, including Tim McGraw, Jo Dee Messina, Collin Raye and Alan Jackson. In 1999, he was named by ASCAP as Country Songwriter of the Year. Later that same year, Vassar was signed to Arista Nashville as a recording artist. His debut album, Phil Vassar, was released in early 2000; it produced five hit singles on the U.S. Billboard country singles charts and was certified gold in the United States. He followed it in 2002 with American Child, Shaken Not Stirred in 2004, and finally Greatest Hits, Vol. 1 in 2006 before Vassar left the label for Universal South Records. His first album for that label, Prayer of a Common Man, was released in early 2008. He has charted eighteen singles on the Billboard Hot Country Songs charts, including two number ones.

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