Mansome is an interesting movie that looks at some of the qualities associated with being masculine, although I could have done with a lot less on the beard guy. And there is humor, so that's always good.
[The film is available on] Netflix instant-watch which I would completely recommend. It's called Mansome, it was made by Morgan Spurlock who you may remember from the documentary Super Size Me. Its lighthearted and features many comedians. It deals with men's struggle to define manliness, especially as current times have ushered an era where it is constantly being redefined (like with the metrosexual movement). It includes interviews with experts and men with varying opinions on the matter.