The filmmakers chose Montgomery wisely; the depth of her personal pain and the earnestness of her striving and optimism give this movie substance it might otherwise lack. According to Montgomery, director Ido Haar originally followed several of Kutiman's YouTube "collaborators," but slowly Presenting Princess Shaw whittled down to become a story about Montgomery, Kutiman, and their beautiful relationship. Kutiman deserves praise for, if nothing else, the joy he brought Montgomery by appreciating her art, by enhancing it, and by being inspired by it. This validation from another artist is what Montgomery -- poor, undereducated, and lonely -- craved her whole life. Watching the tears of joy she experiences after hearing Kutiman's version of her song for the first time is a singular moment that will touch most viewers and should be the kind of emotional truth that documentary makers aim to achieve.
But difficult questions are still raised. Kutiman neither pays nor asks the permission of his many "collaborators." This free use of artistic works uploaded to the internet expresses the philosophy of the free culture movement, which objects to stringent copyright laws and other exercises of ownership and financial control of art. Yet the irony is that, in some sense, Kutiman's efforts to use others' work and polish it into better, more marketable art makes him -- by force of his personality and drive -- exactly the kind of gatekeeper that many talented but financially naïve artists look for in the effort to promote their work. It's not that Kutiman exploits them financially. It's just that these are real people who are attached to the work he collects and uses, so you can't help but feel that they ought to be asked permission. On the positive side, in Montgomery's case, Kutiman's appreciation marked the first time she ever felt encouraged in her art by someone she respects. For that reason, it's hard not to love Kutiman for the hope and self-respect he gives her. The question the movie leaves unanswered is obvious: If there's a marketplace demand for their collaborations, will Montgomery make enough to quit her day job? The movie doesn't say, but in a subsequent interview, Montgomery does announce that she and Kutiman collaborated on an album that's nearing release.