In his work he appropriates pop culture symbols and references to create new meaning using a variety of media including printmaking, sculpture, animation, video, and pamphleteering.
[3] Jennings has made major contributions to the practice of "shopdropping" (a term coined around 2004 to describe the covert placing of art or propaganda into stores).
He was the first to covertly place a completely hand-made art object into a store with his 1998 with his Walmart Project, which features seven art products placed in Walmart stores, including the Mussolini Action Figure,[5] which are humorously critical of aspects of their business practice.
Jennings sent a cease and f**king desist[7] letter to a tech company that used his artwork in their ad to find a new employee.
The site features user-generated step-by-step video and photo/text-based instructions for a wide range of dissenting actions, including (but not limited to): art actions, billboard alterations, shop-dropping, protest strategies, knit-bombing, making protest props, interventions, methods of civil disobedience, stencil work, performative actions, and many other forms of public dissent – from the practical and tactical to the creative and illegal.