He went on to host Saturday Night Live for the first time in 1985 (a show he has since hosted nine times as of 2016), star in films such as Nothing in Common (1986) and Dragnet (1987) before playing his breakthrough role in the age-changing comedy Big (1988).
Ia menjadi pembawa acara Saturday Night Live untuk pertama kalinya pada 1985 (sebuah acara yang sejak itu ia bawakan sembilan kali pada 2016), membintangi film-film seperti Nothing in Common (1986) dan Dragnet (1987) sebelum meraih puncak kariernya dalam film komedi perubahan usia Big (1988).