1945 – He was born in the Letcher County, Kentucky town of Jenkins this year.
1964 – He recorded songs for the small Cory label.
1968 – Stewart made several unsuccessful recordings.
1974 – Other hits from this most commercially successful period until 1977 of Stewart’s career include "Flat Born Natural Good Timin’ Man," "In Some Room above the Street" and "Your Place or Mine."
1970 – Stewart no longer sold records in the quantities of a few years before, but many critics rank recordings from this era, such as "Single Again," as among his best work.
1980 – He recorded an album with producer Chips Moman , Cactus and a Rose, and left RCA for the Hightone label.
1980 – Drug and alcohol problems plagued him this year and his son, Gary Joseph Stewart, committed suicide late in the decade.
1990 – Despite these hardships, Stewart and his wife continued to tour the honky tonk circuit this year, playing venues such as Fort Worth’s Billy Bob’s Texas several times a year.
2003 – He released a live album, Live at Billy Bob’s Texas. But on November 26, the day before Thanksgiving, his wife died of pneumonia. After a month he died with self-inflicted gunshot wound to the neck.