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They include the Vic Lewis Orchestra from 1953–57, the Ronnie Ross-Allan Ganley Jazzmakers, touring North America with them in 1959, and, from 1960-65 he was with the John Dankworth Orchestra.
He led his own small groups intermittently during these times, and accompanied John Dankworth and Kenny Wheeler, among others, on record.
Among those with whom Nightingale has played with are John Dankworth, Cleo Laine, Urbie Green, Carl Fontana, Jiggs Whigham, Clark Terry, Slide Hampton, Thilo Berg, Alan Barnes, Bill Holman, Claire Martin, John Wilson (conductor), Clark Tracey, and Stan Tracey.
His most famous song "Zambezi" became a world hit and was recorded by artists such as Eddie Calvert, Acker Bilk, Bert Kaempfert, The Shadows, James Last, Chet Atkins, Floyd Cramer and Johnny Dankworth.
In 2012 Derek performed with the former John Dankworth Band jazz vocal legend Frank Holder in some concerts featuring the music of Nat King Cole and George Shearing.