Doug had already past the age of 30 when a Nashville manager paired him up with Epic, his first record label. He debuted in1990 with the single, “I’d Be Better Off (In a Pine Box),” the first release from his 1990 self-titled debuted album for Epic records. This album found Pine Box at a number 4 position on the charts with three more in the top 10 ratings. These singles included, “Fourteen Minutes Old”, number 6 and number 5,”These Lips Don’t Know How to Say Goodbye”. Following these songs was his first number one, “In a Different Light”. In addition, the single was nominated for a Grammy Award for Best Country Song. Both this album and its successor, 1991’s I Thought It Was You, earned a platinum certification from The Recording Industry Association of America for U.S. shipments of one million copies. Two more albums for Epic, 1992’s From The Heart and 1994’s More Love, each was certified gold. Stone has charted –twenty-two singles on Hot Country Songs, with his greatest chart success coming between 1990 and 1995. In this time span, he charted four Number Ones: “In a Different Light”, “A Jukebox and a Country Song”, “Too Busy Being in Love”, and “Why Didn’t I think of That”, and eleven more Top Ten singles.
In early 1992, Stone found that one of the arteries in his heart was almost entirely blocked. He underwent quadruple bypass surgery and took time off to recover, just as his third album, "From the Heart," was released. With a gold certification for shipments of 500,000 copies, "From the Heart" included two Number Ones among its four singles: “Too Busy Being in Love” and “Why Didn’t I Think of That.” The other two singles were “Warning Labels” and “Made for Lovin’ You,” at No. 4 and No.6 respectively. One month later Stone released an album titled "The First Christmas."
In June 1994 Stone discovered that he was having breathing problems, which were affecting his singing. Doctors at Vanderbilt University’s medical center failed to find any problems in his throat. A second consultation revealed a lump in his nostril but amazingly it was not cancerous. While Stone was undergoing treatment, his Greatest Hits, Vol.1 compilation was released in late 1994.This album included the new song “Little Houses, “which debuted on the charts in October 1994 and peaked at No. 7 in early 1995.