Early life and career
Obeysekera graduated from the University of Ceylon in 1962. He served on the Editorial Staff of the Associated Newspapers of Ceylon Limited from 1964 to 1970. In addition to his editorial work, Obeysekera wrote several short stories during this period.

Obeysekera entered the film industry with Sath Samudura in 1967 which he co-wrote and worked on as assistant director; it was Sri Lanka's entry at the Moscow International Film Festival. In 1971 he was awarded a certificate in Cinematography by the Comité de libération du cinéma français.

1970s
In the 1970s Obeyskera wrote and directed Ves Gaththo ("Masked Men") (1970), Valmathuwo ("Lost Ones") (1976), Diyamanthi ("Diamond") (1977) and Palangetiyo ("Grasshoppers") (1979). Palangetiyo won the Presidential Film Awards for Best Screenplay, Best Director and Best Film.

1980s
1983's Dadayama ("The Hunt") also won the Presidential awards for Best Screenplay, Best Director and Best Film. It was a commercial success as well. Obeyskera made Kedapathaka Chaya ("Reflections on the Mirror") in 1989 after a five year break.[1]

1990s and 2000s
In the late-'90s, Obeysekera made Maruthaya ("The Storm") (1995), Dorakada Marawa ("Death at the Doorstep") (1998) and Theertha Yathra ("Pilgrimage") (1999). These also secured several OCIC and Presidential Awards.

Salelu Warama ("Web of Love"), Agni Warsha, Aganthukaya, and Sewwandhi were made in the 2000s.