He was born in New York to Ray Kennedy, Sr., the National Vice President for Sears and the man behind the Discover credit card. His father's work kept young Kennedy and his family on the move. As a teen, his parents refused to get him a guitar, so Kennedy built his own. He briefly attended college where he majored in business, but at that time he found himself drawn to music and dropped out to play in midwestern clubs. He spent some time in Oregon and in 1980 moved to Nashville where he built his own studio and learned engineering when he began recording his own demos. He got his start as an engineer and was responsible for producing most of Tree Publishing's Pop demos during that time. Pop singer Stevie Nicks recorded one of his songs, "Battle of the Dragon," and Kennedy became a staff writer at Tree where his tunes were occasionally recorded by John Anderson, Charley Pride, David Allan Coe and others. Because his songs weren't selling well enough to suit him, Kennedy decided to become a recording artist and cover them himself.

In 1990, he signed to Atlantic Records and debuted with What a Way to Go. Kennedy not only produced the album in his own studio, he also played all of the instruments but the dobro, steel guitar and Wessenborn. He also penned or co-penned all of the songs on it. Kennedy made his single debut with the album's title track, which peaked on the Top Ten with the album making it to the Top 60. He released two more singles from the album, but they only became minor hits. In 1991, he produced and engineered an album for songwriter Don Henry, Wild in the Backyard. In 1992, Kennedy teamed up with producer/songwriter Monty Powell and made Guitar Man.