The most happening actor in the Malayalam cinema Dileep- entered the malayalam film industry as a mimicry artist who wanted to be an actor, but then started assisting directors like Kamal. He got his first break in a tiny role of Kamal's film Ennodu Ishtam Koodamo'(1992). And the films which came afterwards like Manathe Kottaram (1994), Kakkakkum Poochakkum Kalyanam(1996) etc proves him as a good comedy actor. Sallapam(1996) a hit movie of sunder das in which he played as a hero gives him a break as a hero in his film career. Later comes , Thenkasipattanam(2000) and Rakshasaraajavu(2001)as supporting actor which all become hits.

But it was in a movie named Joker(2000) directed by Lohitdas which unchained him from the type comedy roles he had at his hand. He played the role of the joker, who always wore a smile at his face and was making others life even when he had a whole lot of personal agonies hid within his heart. He handled the character with easiness that he never had to look back after the film's stupendous success.

Subsequently, after the film 'Joker' his demand as a successful hero started with hit after hit like Thenkasipattanam (2000), Ishtam(2001), Ee Parakkum Thalika (2001), Kalyanaraman (2002),  Thilakkam (2003),C.I.D. Moosa (2003) (which he produced himself). But there is a critics to have brought that he has been type cast in slapstick comic roles. He fared as an action hero in Runway(2005), Lion(2006), Chess(2006), DON(2006). In them Runway and Lion were super hits. 

In the movie Meesa Madhavan (2002) his attempts to give completeness to the character as an actor, which give rising to new heights in his career. Experimenting with odd roles like as an ugly-looking, crippled hunchback in mentally retarded person in Thilakm(2001), Kunjikkoonan (2002), a  transvestite man from the family of fishermen in Chanthupottu (2005),Pachakkuthira (2006) etc give him much acclamation to him as an actor. He won the Kerala State Film Special Jury Award for Kunjikkoonan (2002) and Chanthupottu (2005)

Dileep married actress Manju Warrier on 20 October 1998 but later the couple filed for divorce which was granted on 31 January 2015.The couple has one daughter named Meenakshi. After long speculations regarding his relationship with Malayalam actress Kavya Madhavan, he married her on 25 November 2016.The couple have acted in 21 films together, being the lead pair in 16 of them.

Over the years he has attained a particular position in the hearts of Malayalam film goers. He handles comedy and action effortlessly, a feet only a few can boost off.