Dileep was born in Kerala as Gopalakrishnan Padmanabhan Pillai in the year 1968. His career started as an assistant director to Kamal. He was named as Dileep through the character he performed in his debut movie. His debut movie as a hero was in the year 1994 through Manathe Kottaaram as Dileep. Sallapam and Punjabi House made him get popularity among the Malayalam audience. Before his film entry, Dileep was a mimicry artist. He worked in Kalabhavan too.

While assisting Kamal in his films, Dileep showed off his face in some films too. His natural acting skill paved him a way to reach good heights in the Malayalam cinema. One of his best movies is Kunjikoonan, in which he acted as a hunchbacked man. He got the special Jury Award for his performance in this film. Chanthupottu was his next movie that gifted him a special jury Award for his excellent performance. In this film, he acted as an effeminate. He has lots of courage to do the challenging roles, which others hesitate.

He married actress Manju Warrier in the year 1998 and got divorced in 2015. This couple has a beautiful daughter Meenakshi. Dileep has also produced films and got success too. He has an interest in singing and has sung few songs in the films such as Sringaaravelan, Sound Thoma, Thilakam, Kalyaanaraaman and Chandranadikkunna Dikkil.