This essay explores the work of new media artist, Tony Oursler. Beginning his career in video art during the seventies and eighties, his work has evolved into a mashup of techniques and mediums. He uses digital imagery, project, sound, paint and photography to create his provactively orchestrated scenes. For example, in his installation Face to Face (2012), Oursler displays twenty works in which each character of his creation consists of mismatched faces, distorted heads, and alien-like features.Additionally, the mutated forms spew moronic babble broadcasting senseless chatter through their unnerving glistening smiles and disconcerting puckered lips. Intent on tempting us, illuminating our vulnerabilities and desires for affection, the characters in Face to Face utlimately enterain us with their humorous antics. However, further scrutiny shows that Oursler's humor is a tool that unmasks discomfort. In the majority of his artwork, Oursler criticallly, paradoxically and humorously explores the connection between human and machine. In "Oursler's Laughing Machine," I compare his work to other digital artists' installations in order to deconstruct how Oursler uses altered forms of language, babbe and laughter, to elicit a diversity of emotive and highly fabricated states in the minds of his prospective viewers.