Dileep was born in Desom, Aluva, Ernakulam district, Kerala. He started his career with Kalabhavan, as a mimicry artist. His small comedy roles in many films were noteworthy.
He became a popular actor in Malayalam industry with his movie 'Sallapom', in which he acted opposite Manju Warrier who later became his wife. This film was a turning point in his film career.
Dileep's popular films include Sallapom, Kudamattom, Ee Puzhayum Kadannu, Kalyana Sowgandhikam, Kaliyoonjal, Sundarakilladi, Punjabi House, Kaikudunna Nilavu, Deepasthambham Mahascharyam, Chandranudikkunna Dikhil, Joker,Meesha Madhavan, Dosth, Kalyanaraman, Kunjikkoonan, C.I.D. Moosa, Runway, Perumazhakkalam, Pachakkuthira, Inspector Garud, Vinodhayatra, Calcutta News, Twenty:20, etc.