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Gamble Rogers balanced a love of balladry and folk songs with a passion for the oral tradition and storytelling. The son and grandson of influential architects, Rogers was described as both a "modern troubadour" and the "resurrection of Will Rogers and Mark Twain". Capable of enchanting an audience with Travis-style guitar flatpicking, Rogers was as effective relying his latest tales about the inhabitants of the fictitious Oklahowa County. The Atlanta Constitution called Rogers, "an American treasure worthy of inclusion in the Smithsonian".

Rogers first attracted attention as the lead, acoustic and electric guitarist for the folk ensemble, The Serendipity Singers. His interests in tale-spinning became evident after Rogers became spokesperson for the group on such television shows as The Tonight Show, Hootenanny and The Ed Sullivan Show.

Leaving the Serendipity Singers after two years, Rogers returned to Florida and focused on his solo career. Rogers made many television appearances in the late-1970s including writing the theme song for a thirteen episode series on the Philadelphia Folk Festival, starring in his own PBS special, Live At The Exit/In and co-hosting and starring the 1985 special, AT&T Presents Carnegie Hall Tonight. Between 1982 and 1984, Rogers served as a weekly guest commentator on National Public Radio's All Things Considered.

The author of many plays and dramatizations, Rogers was heavily influenced by novelist James Faulkner, who he met while attending the University of Virginia. His first play, Good Causes: The Confessions Of A Troubadour, was presented on National Public Radio's drama hour in 1977. Earplay, Rogers' second play, was presented on National Public Radio's show, Folk Festival U.S.A. in 1980. Rogers' first dramatic screen play for television, The Waterbearer, was produced by PBS in 1984. Oklawaha County Laissez-Faire, Rogers' one-man play, was completed in 1990.

Music remained an important part of Rogers' career. His concerts, which combined songs and stories, often found him with his guitar strap slung around his shoulder while he told a long, humorous, narrative. Between 1988 and 1991, Rogers served as an official ambassador for the Florida Division of Tourism and the Florida Folk Festival.

Rogers was just hitting his peak when he died, on October 10, 1992, trying to save a man from drowning. The recreational area in St. Augustine, where the accident occurred, was later renamed, "The Gamble Rogers Memorial Park". In the liner notes of his album, Fruitcakes, Jimmy Buffett dedicated the recording to Rogers' memory and wrote that Rogers, "taught me how to move an audience with dialogue and delivery as much as with music". In 1993, Rogers was posthumously awarded a Folk Heritage award. ~ Craig Harris, Rovi