Architecture can be funny. Of course, it often makes for a well-disposed butt of the joke, like when Frank Gehry is satirized on the Simpsons, but buildings themselves can be funny as well. Philosophers like Kant believed humor was in the incongruity between what is expected and what is experienced. There are all sorts of expectations placed on buildings and an infinite number of ways that incongruity might grow between those expectations and what a building actually delivers. This video explores some of the most interesting of these humorous buildings through history, from Giulio Romano’s Mannerism, to SITE Architects BEST stores, and many more. Finally, it points to some contemporary practices that deploy humor to achieve more than just a chuckle.