Because Redbone first emerged as a performer in Toronto during the 1970s, he was believed to be Canadian; his work, a revival of pre-World War II ragtime, jazz, and blues sounds, recalled the work of performers ranging from Jelly Roll Morton and Bing Crosby to blackface star Emmett Miller. He made his recording debut in 1976 with On the Track, which featured legendary jazz violinist Joe Venuti as well as singer/songwriter Don McLean; his 1977 follow-up Double Time even reached the U.S. Top 40 charts, largely on the strength of his frequent appearances on television's Saturday Night Live.

After 1978's Champagne Charlie, Redbone began recording only sporadically; following 1981's Branch to Branch, he waited four years before reentering the studio to cut Red to Blue. Invariably, his albums featured guest appearances from an eclectic cast of luminaries: while 1987's Christmas Island included a cameo by Dr. John, 1994's Whistling in the Wind included duets with Ringo Starr and Merle Haggard and 2001's Any Time featured contributions from such jazz luminaries as guitarist Frank Vignola, reedman Ken Peplowski, and bassist Jay Leonhart. Despite his low profile, Redbone has also earned a certain measure of fame as a fixture in various television advertising campaigns.