He began acting as a professional in 1964 after he joined the "Oyin Adejobi theatre group" and the first role he played was Adejare in Orogun Adedigba, which was Oyin Adejobi's autobiography.[6]
After he spent nine years with Oyin Adejobi, he joined the University of Ife theatre, where he worked with the late veteran dramatist and scholar, chief Ola Rotimi.[7]
Kola Oyewo was known for the role he played as "Odewale" inThe Gods Are Not to Blame, a drama by Ola Rotimi.[8]
In 1996, Oyewo joined the services of Obafemi Awolowo University, where he rose to the rank of senior lecturer before retiring in September 2011.[9] After his retirement from Obafemi Awolowo University, he joined the services of Redeemer's University, where he currently serves as head of the department of dramatic art.[10] He is currently working at Elizade University Ilara-Mokin, Ondo State as a performing arts lecturer.[11]