While his gravelly baritone and omnipresent fedora, dark glasses, and Groucho Marx mustache made him one of the more distinct and recognizable characters in popular music, little is known about the neo-vaudeville crooner Leon Redbone. Throughout his career, he steadfastly refused to divulge any information about his background or personal life; according to legend, Redbone's desire to protect his privacy was so intense that when he was approached by the famed producer John Hammond, the contact number he gave was not his own phone, but that of a dial-a-joke service.

Because Redbone first emerged as a performer in Toronto during the 1970s, he was believed to be Canadian, though some sources have cited his birthplace as the Greek island of Cyprus or Philadelphia, Pennsylvania. A Canadian magazine profile in the '80s reported that his birth name was Dickran Gobalian, though Redbone has never confirmed or denied that. His musical style was a revival of pre-World War II ragtime, jazz, and blues sounds, recalling the work of performers ranging from Jelly Roll Morton and Bing Crosby to blackface star Emmett Miller.

Redbone first came to the attention of mainstream music fans when Bob Dylan saw him perform at the 1974 Mariposa Folk Festival in Ontario. Several months later, Dylan spoke about him in an interview with Rolling Stone. "Leon interests me," Dylan said. "I've heard he's anywhere from 25 to 60, I've been [a foot and a half from him] and I can't tell, but you gotta see him. He does old Jimmie Rodgers, then turns around and does a Robert Johnson."

Redbone landed a recording contract with Warner Bros. and 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 re-entering 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. After a long layoff from recording, Redbone returned in 2014 with Flying By.

Despite his low profile, Redbone earned a certain measure of fame as a fixture in various television advertising campaigns, as well as frequent television appearances and his vocal cameo as a singing snowman in the 2003 movie Elf. In 2015, Redbone announced he was retiring from live performances, citing health problems. A year later, Jack White's Third Man Records released Long Way from Home, a collection of Redbone's early radio performances recorded in 1972. A short documentary about the singer, Please Don't Talk About Me When I'm Gone: The Search for Leon Redbone, was released in 2018. Redbone retired from performing in 2015, with his spokespeople revealing he was dealing with health problems, and his death was announced on his official website on May 30, 2019. While Redbone's age at the time of his death was 69, the official statement cheekily referenced the mystery of his age and background by declaring, "Leon Redbone crossed the Delta for that beautiful shore at the age of 127." ~ Jason Ankeny, Rovi