Oscar Kightley was born in Samoa and immigrated to New Zealand with his mother when he was four years old. Oscar first recognised his ability to make people laugh when he was a schoolboy, and at Rutherford High, he developed his skills in humour and English (but not maths!) further. Following a cadetship at The Auckland Star, Oscar moved into working in radio and television starting behind the scenes and then moving to a presenting role with Life in The Fridge based in Christchurch.
Oscar co-founded Pacific Underground and the Island Players theatre company which has produced critically acclaimed work. Oscar won the Bruce Mason Playwriting Award in 1998 and has worked as a performer and writer for a number of television shows including Skitz, Telly Laughs, The Panel, Sportzah and TV3's rugby coverage. His plays include Fresh off the Boat which he co-wrote with Simon Small, Dawn Raids, Island Girls, A Frigate Bird Sings co-written with Dave Fane and Nathaniel Lees, and Niu Sila co-written with Dave Armstrong.
Oscar also co-wrote and took a lead role in the highly successful Sione’s Wedding movies. He was one of the Naked Samoans, who took their anarchic brand of comedy around the country and to Edinburgh. Oscar co-wrote bro’Town with David Fane, Mario Gaoa and Shimpal Lelisi and is well known for his voiceover character Vale.
Oscar wrote for the television series Supercity. In 2013 he played the title character in the police drama Harry, which he also co-wrote. He directed Madeleine Sami's television comedy Super City, and co-directed a US pilot of it with Taika Waititi.
A 2006 Arts Foundation Laureate Award winner and Qantas award-winning journalist, Oscar was appointed to the Council of Creative New Zealand in 2007. In 2008, he was awarded a Sir Peter Blake Trust Emerging Leader Award. In 2009 he was awarded member of The New Zealand Order of Merit for his services to television and theatre.
In 2016 he was awarded the Senior Pacific Artist Award with Dave Fane at the Creative New Zealand Arts Pasifka Awards and in 2019 received the Fulbright-Creative New Zealand Pacific Writer's Residency at the University of Hawai'i at Mānoa.