The Stu Osborn Show is a 2007 web viral video advertisement for Microsoft. It is made to look like a mockumentary of a fictional television interview show of the same name. The video is directed by Christopher Guest who is well known for being the creative force behind other mockumentaries like Waiting for Guffman and Best In Show. It stars Michael Hitchcock as Stu Osborn, the awkward and somewhat disoriented "host" and Fred Willard as a failed businessman-turned-author who is Osborn's "guest." Much of the dialogue is improvised by the actors. Both Hitchcock and Willard are frequent performers in Guest's films.
The video was produced by the Los Angeles-based ad company Go Film. It won a Webby Award in the Branded Content category.
Microsoft presented the video through its now defunct MSN Soapbox service.