Cosby ya fara aikinsa ne a matsayin mai ban dariya a cikin yunwa i a San Francisco a lokacin shekarun 1960. Daga nan sai ya sami rawar gani a cikin gidan talabijin na I Spy, sannan kuma ya nuna wasan kwaikwayonsa na Bill Cosby Show, wanda ya gudana na tsawon yanayi biyu daga 1969 zuwa 1971. A shekara ta 1972, ta amfani da Fat Albert hali da aka bunkasa a lokacin da yake tsayawa, Cosby ya kirkiro, ya samar, kuma ya shirya jerin shirye-shiryen talabijin na Fat Albert da Cosby Kids wanda ya gudana har zuwa 1985, wanda ya mayar da hankali kan ƙungiyar matasa da ke girma a cikin birane. A cikin shekarun 1970, Cosby ya buga fina-finai kusan rabin dozin, kuma lokaci-lokaci ya koma fim a baya a cikin aikinsa. A shekara ta 1976, ya sami Doctor of Education daga Jami'ar Massachusetts, Amherst.
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