"[1] Olaiya was born on 31 December 1930,[2] in Calabar, Cross River State, the 20th child of a family of 24.
His parents, Alfred Omolona Olaiya and Bathsheba Owolabi Motajo, came from Ijesha-Ishu in Ekiti State.
His father's house, Ilọijọs Bar, stood at 2 Bamgbose Street, Lagos Island, until it was demolished in September 2016.
[3][6] In 1954, Olaiya formed his own band, the Cool Cats, playing popular highlife music.
[3] Olaiya also ran a business that imported and distributed musical instruments and accessories in West Africa, he also established the Stadium Hotel in Surulere.
[3] Both the drummer Tony Allen and vocalist Fela Kuti played with Olaiya and went on to achieve individual success.