'Zoolander', of course! But also, I found 'The September Issue' a pretty fascinating insight into Anna Wintour. “In Vogue: The Editor's Eye” is on HBOGo and is a decent overview, but pretty broad otherwise. “Picture Me” is a great documentary on the life of a model, shot by the model herself; after having my toe in that world, and interacting with hundreds of agency models, I can say it paints a pretty sobering picture of that life.
By ‘photo viewer’ I’m assuming you mean library/catalog software? I use both Bridge and Lightroom :-)