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He had a minor solo hit in 1957 called "That Crazy Feeling".
After sales slowed down, Rogers joined a jazz group called The Bobby Doyle Three, who got a lot of work in clubs thanks to a reasonable fan following. They disbanded in 1965, and a 1966 jazzy rock single Rogers recorded for Mercury Records, called "Here's That Rainy Day", failed.
Producer Larry Butler and Rogers began a partnership that would last four years.
After leaving the First Edition in 1976, after almost a decade with the group, Rogers signed a solo deal with United Artists.
Two of his albums, The Gambler and Kenny, are featured in the poll of "The 200 Most Influential Country Albums Ever".
Later success includes the 2006 album release, Water & Bridges, an across the board hit, that hit the Top 5 in the Billboard Country Albums sales charts, also charting in the Top 15 of the Billboard 200.
Rogers also worked as a producer, writer and session musician for other performers, including country artists Mickey Gilley and Eddy Arnold.
In 1966 he joined the New Christy Minstrels as a singer and double bass player.