In the years after the Second World War, a golden age of economic growth seemed set to fulfil the historian James Truslow Adams’ celebrated description of the American Dream ‘of a land in which life should be better and richer and fuller for everyone, with opportunity for each according to ability’. By the end of the 1960s, a flurry of political assassinations, civil unrest and the escalation of the Cold War precipitated a national crisis of confidence that reached its apogee with the 1973 oil embargo.

The title of this exhibition, borrowing from the evocative slogan painted across Jean-Michel Basquiat’s Peruvian Maid (1985), conjures a society running on empty. Its artists – loosely linked by a network of personal and professional relationships, as between Cady Noland and Steven Parrino, Jenny Holzer and Barbara Kruger, Richard Prince and Christopher Wool – chronicle a dramatic ideological shift. If the prevailing atmosphere is of disillusion, then it is not without hope: with the end of a dream comes a renewed engagement with reality.

In deconstructing the national self-image, these artists brought a combination of physical violence and intellectual wit to bear on the symbols of America − the Stars and Stripes, the cowboy, the dollar bill − that Pop had seemed to celebrate. They adopted humour, appropriation and inauthenticity as strategies by which to challenge the ideologies inscribed within these signs, opening up the space between the authorised narratives of the United States and the darker histories they concealed.

Noland’s hole-ridden Cowboy Bullethead Movie Star (1990) and Untitled (Walker) (1989) profane these sacred symbols of American life. For the latter, the artist draped the Stars and Stripes over a clothes rail attached to a zimmer frame and basket. Re-inscribed in an assemblage that signals decrepitude, the limp flag reads like a challenge to American culture’s continued claim to virility and youth: the nation, like the sign, is exhausted. Or perhaps the flag alludes to violent death − draped over the coffin of a soldier returning from war − and by extension the draft, identified by Malcolm X as a structural expression of state violence against African-Americans.

Enshrined in the collective consciousness as the historical guarantor of national independence and individual freedom, violence is not only central to the self-image of the United States but − as Noland has proposed in an interview with Michèle Cone − has a broadly positive reputation within it.1 Where Noland identifies and critiques an aggressive streak in the collective psyche, Robert Mapplethorpe undermines another foundation of the American society. Photographed with an illuminated back light, his Dollar Bill (1987) is a double exposure that literalises the idea of seeing through a sign.

David Hammons drapes himself in the flag in Untitled (Body Print) (1975), an identification it seems safe to characterise as double-edged. The work foreshadows his creation of the hybrid African-American Flag (1990) that now hangs outside the Studio Museum in Harlem and which intertwines the official history of the United States with those of colonialism, slavery and rebellion. It also draws to mind the fig leaf, and the implication that the black body might affront his audience is seconded by Close Your Eyes and See Black (1969), in which the artist’s face − hands over eyes − is superimposed on the print left on the paper by his inked torso. The impression is of a body pressed up against a pane, uncomfortably confined.

Hammons’ enigmatic Phat Free (1995/99), for which the artist was filmed kicking a bucket down the street at night, puns on a common euphemism for death. Sigmund Freud, who popularised the idea that dreams are the bowdlerised expressions of much darker impulses, also identified jokes as a means of camouflaging latent aggressions. That self-destructive public behaviour can double as mass entertainment seems self-evident in the current political circumstances. However innocent they might appear on the surface, both dreams and jokes are founded on unconscious fears, anxieties and hostilities.2 This might explain why the spectacle of violence described by Bruce Nauman’s Double Poke in the Eye II (1985) is so funny, and which makes Richard Prince’s paintings an apt choice for this exhibition.

By painting jokes onto deadpan monochromatic backgrounds, Prince lays bare the insecurities underpinning expressions of humour: sexual dissatisfaction, fear of mortality, latent aggressions. The disruptive element of the joke, which allows different and sometimes dangerous meanings to attach to ostensibly harmless statements, is exaggerated by its having been ostracised from its original, ‘safe’ context in a magazine or joke book. Set amidst these degraded symbols of American society, they seem harsher, funnier, more sinister. Too close, perhaps, to the bone.

Similar processes are at work in the phrase that Holzer has isolated and embossed in her 2012 plaque − ‘Someone wants to cut a hole in you and fuck you through it, buddy’. Like a joke, its phrasing normalises a disturbing subliminal conflation of sex and violence. Exposing the violence embedded in language, the text pieces of Holzer and Kruger reassess the broader contexts in which words work. In common with Prince and Wool, albeit by different means and to different ends, they subvert the dominant discourse by liberating words and phrases.

The hole − as window, wound or breach − is among this exhibition’s most compelling motifs: in the threat or diagnosis of Wool’s Head (1992), in Parrino’s easy rider biker overlaid with handcuffs, in Robert Gober’s Untitled (Drain)(1993) and Untitled (Man Coming out of a Woman)(1993−94). Holes compromise the boundaries, literal and figurative, by which society is segregated and structured. Larry Clark’s photographs are like peepholes between the pristine white-walled exhibition space and the wider culture, exciting the desire and shame that have long characterised the relationship of the very wealthy to those on the fringes of society.

The theme of division is literalised by Basquiat’s witty and part-whitewashed two-part canvas 2 for a dollar (1983), one of several works to address the mechanisms of exchange that drive both the art world and the society of which it is a microcosm. The elaborate wrought iron gates implied by Wool’s Untitled (1988) also separate America’s wealthiest citizens from its poorest. Hammons, meanwhile, adopts the visual language of the museum, a veil pulled back to reveal an elaborately framed splash of Kool-Aid.

These artists sought by different means to reacquaint their audience with the uncomfortable truths beyond the American Dream. In the intervening decades that illusion has been replaced, at least in part, by a narcissistic culture of celebrity and spectacle. By punching holes in the mirror that art holds up to society, the work gathered together in ‘From the Vapor of Gasoline’ offers strategies of use to artists working in comparably fraught times.