Bennett's subject is depicted through the central figure of an Indigenous Australian man's decapitated torso in of Van Gogh's Bedroom in Arles (1888) with blood spurting from his gaping neck.

In painting the composition of Outsider during 1988, Bennett attempted to realistically depict the marginal effect of the First Fleet and "to question the way power is exercised (by) disputing claims to domination".

Bennett feared that the romanticised images of ships, danger and adventure faced by the First Fleet were contributing to the reinforcement of Australia's colonial identity through the lens of a selective history and to be deemed as the mainstream.

[18] Some individuals have come to regard his expression of an Aboriginal point of view as a 'guilt trip' designed to make non-Indigenous Australians feel guilty about Australia's past.

[20] By recontextualising images Bennett seeks to incite change and to create a "turbulence in the complacent sense of identification with… history" where new possibilities for representation can arise.

[21] The grotesque inspired Bennett to disrupt the serene quality of colonial images and the complacent acceptance of Australia's glorified history which had untruthfully glamorised and depicted the peaceful settlement of the Australian landscape.

[15] His inspiration for the depictions of spurting blood is also sourced through Aboriginal funeral ceremonies in which ritualised public displays of grief and mourning can involve blood-letting and the cutting of one own's body.

[15] Outsider opens interpretations to a broad range of philosophical ideas related to the construction of identity and perception through Bennett's experiences of Australia's colonial past and postcolonial present.

Hugh Ramsey Chair of Australian Art History, Ian McLean expands on Bennett's appropriations by calling Outsider a "metaphysical quest for meaning and identity".

Professor of philosophy, Melvin Rader has commented on the manifestoes of recent (art) schools and expresses how those within, such as Van Gogh, face feelings of "opposition and estrangement" as well as "madness and suicide" which is what Bennett sought to explore and display within his painting of Outsider.

[25] However Bennett's own appropriation is a violent ritual rather than Van Gogh's one of tense calmness, which McLean claims is "transparently staged, his mutilation is a public theatre rather than a private act of desperation".

[25] The walls of the room are occasionally spattered with red hand marks which artist Adam Gezcy interprets to be "the most venerable Aboriginal sign of both presence and absence".

[3] Another critic, Art Historian Jeanette Hoorn suggests that Van Gogh's Bedroom at Arles and The Starry Night are "modern icons of Europeanness" and are objects of admiration by cultures of the West which Bennett appropriates against "black memories of violence and mutilation".

[26] The mutilation is interpreted to be an allusion toward bounty hunters in early colonial Australia who decapitated black men in exchange for money in Europe.

The spurting blood from the neck of the Indigenous Australian has assimilated into and has been replaced by the culture of the West's 'Starry Night' which Hoorn suggests is reinforced by the "representation of classical statuary" in the painting.