Roger Bennett's parents were Elliott and Ada (nee Conelly) Bennett. His father was 'Elley' Bennett, champion bantam and featherweight boxing fighter. Bennett spent his childhood in Brisbane. When he was older, he spent many years incarcerated at various prisons. After his stint in Yatala, Bennett changed his focus in life and decided to further his education at the South Australian Institute of Technology. He then moved to Alice Springs, where he worked for the community, in different programs for rehabilitation, aged, youth and prisons. If a wage could not be paid, Bennett would often volunteer his time and skills.
His first performance as an actor was in the Comet Cabaret in 1986. Then in 1988, he was Assistant Director for the Playbox Theatre production of Ray Mooney's Black Rabbit. In 1990, his play Up the Ladder was produced by Adelaide's National Aboriginal Cultural Institute, Tandanya, and later produced by the Melbourne Workers Theatre in 1995. His play Funerals and Circuses made its debut at the 1992 Adelaide Festival. Then in 1993 the play was performed at the Melbourne International Festival and the National Festival of Australian Theatre in Canberra.
Bennett has participated in the National Black Playwrights Conference as an actor and writer. He was writer-in-residence at Tandanya and at the Araluen Arts Centre in Alice Springs. In 1995, Bennett was commissioned by IAD Press to compile and edit Voices from the Heart : Contemporary Aboriginal Poetry from Central Australia.