Based on the popularity of his music, he formed the Bobby Benson Jam Session, a dance band that played swing, jive, sambas and calypsos.

[5] Various prominent musicians started out playing in Benson's band, including Roy Chicago, Sir Victor Uwaifo, Bayo Martins and Zeal Onyia.

[1] Victor Olaiya started as a trumpeter with Bobby Benson's band, and became one of the first Nigerian musicians to play highlife with his group the "Cool Cats".

[7] "Taxi Driver", his biggest hit, and "Niger Mambo", an African melody with the Latin beat, were covered with different interpretations by American artists such as Stanley Turrentine and Jackie McLean.

[8] Randy Weston covered "Niger Mambo" in a solo performance on his 1978 album Rhythms-Sounds Piano, describing the piece as representing exactly what is called "high life style" in West Africa.