Secretary (2002)

ScreenThis movie touches on some, more than, risqué subject matter that just dives deeper and deeper as the movie progresses.  The cyclical format of the film persists from the start until just before the end.  This seems to play on the use of both classical and operant conditioning found in the film.  The ever present and in your face masochistic theme is not a new concept behind a film, but this one is also a comedy.  At the end of the day, if you like Maggie Gyllenhaal in kinky situations than this is your movie.