Bernard Olabinjo Benson was born in 1921. He hailed from Ikorodu, Lagos State. Benson had his elementary education in Lagos, attended Enitonia High School, Port Harcourt and later CM.S Grammar School, Lagos .

Bobby formed the Negro Ballet and toured the European capitals. Bobby returned to Nigeria with wife, Cassandra, who he met in Britain and established the Bobby Benson and Cassandra Theatrical Group.

Bobby remains the undisputed pioneer of Highlife music in Nigeria . Bobby found the rhythms of Highlife music so irresistible that he waxed the song "Taxi Driver" which became a classic hit in West Africa with several versions of it produced by other musicians.

Bobby was a master entertainer and a comedian whose charismatic disposition thrilled his audience and set the dance floor rolling. Prominent musicians like Dr Victor Olaiya, Eddy Okonta, Roy Chicago, Sir Victor Uwaifo, Bayo Martins and Zeal Onyia have at one time played in Bobby's band. He remains the first Nigerian to ever own a Night Club (Caban Bamboo) as well as a hotel. Some of his other evergreen hits are" Gentleman Bobby", Iyawo se wo lose mi, "etc. Benson died in Lagos on Saturday May 14, 1983.