Reid was born in Norfolk, Virginia, the son of Augustine (née Wilkins) and William Lee Reid.[1] He earned his Bachelor of Business Administration at Norfolk State College in 1968. Reid also became a member of Alpha Phi Alpha Fraternity, Incorporated.[2] After graduation he was hired by Dupont Corporation, where he worked for three years.[2]
Reid's entertainment career also began in 1968, under atypical circumstances. He and insurance salesman Tom Dreesen met at a Junior Chamber of Commerce meeting near Chicago.[3] They were "put together to promote an anti-drug program in the local schools" and, prompted by a comment from a child, decided to form a comedy team.[3] The team, later billed as "Tim & Tom", was the first interracial comedy duo. Years later, Reid and Dreesen co-wrote a book about those years called Tim & Tom: An American Comedy in Black and White (ISBN 978-0-226-70900-0, co-written with sports writer Ron Rapoport).