He also co-wrote singles for Holly Dunn, Tim Mc Graw, and Jo Dee Messina, and has recorded with Mary Chapin Carpenter, George Jones, and Marty Stuart.
Diffie released seven studio albums, a Christmas album and a greatest hits package under the Epic label.
Diffie has said that his "Mom and Dad claimed that [he] could sing harmony when [he] was three years old." His family moved to San Antonio, Texas while he was in the first grade, and subsequently to Washington state where he attended fourth and fifth grades.Later, he moved to Wisconsin for the years he was in sixth grade through his second year of high school, and back to Oklahoma where he attended high school in the town of Velma.He also released one studio album each through Monument Records, Broken Bow Records, and Rounder Records.Among his albums, 1993's Honky Tonk Attitude and 1994's Third Rock from the Sun are certified platinum by the Recording Industry Association of America; 1992's Regular Joe and 1996's Life's So Funny are both certified gold.
Between then and 2004, Diffie charted 35 cuts on the Billboard Hot Country Songs chart, including five number one singles: his debut release "Home", "If the Devil Danced (In Empty Pockets)", "Third Rock from the Sun", "Pickup Man" (his longest-lasting number one, at four weeks) and "Bigger Than the Beatles".In addition to these cuts, he has 12 other top ten singles and ten other top 40 hits on the same chart.