The American 1960s has become closely associated with moral crusades that strove for Civil Rights for the black community and protested against the conflict in Vietnam, with the peace and love gestures of the hippies to the fore, particularly in the latter part of the decade. This essay argues, however, that the seeds of a more subversive underground movement would be sown during the period and a new approach to art creation, centred on an emerging trash aesthetic, would not only challenge the psychedelic utopianism of the organised counterculture but actually leave a longer-lasting mark on left-field creative activity in the final quarter of the century. As Andy Warhol’s art and film projects were re-shaped as multi-media experiences, the importance of the Velvet Underground, the rising house band at the artist’s Factory headquarters, was magnified. The Exploding Plastic Inevitable, a performance work inspired in part by early-decade Happenings, would be unveiled in 1966, combining Warhol’s underground cinema projections, light shows, dancers and the cacophonous sound of the Velvets. This radical piece of stage art was filmed by the director Ronald Nameth and his account remains a key document of the live venture. The article proposes that while Warhol and the band built on traditions from Dada to the Beats to build a form of anti-art, it was during this key time that the ideas of trash, from the Pop Art celebrations of mass cultural forms to the darker delvings of his movies, and his adopted rock group, into the decadent realms of drugs and sexual perversity – took crucial shape. This anti-aesthetic would have an enduring impact beyond the subterranean avant-garde of New York City in the years that followed as music and cinema, art and literature were all shaped by this brand of expression and examples of its legacy are suggested.