You overpraise Blow Out, which does have its greatness, but Nancy Allen performs in a high squeaky affected New Yawk voice that - much as I love her - she is nowhere near qualified to pull off. So much of the film rests on her shoulders it sinks the entire enterprise.
I'm fairly certain it would get destroyed in the next round.
Then again, Hardly Working isn't going much further either, but I like your reasons for advancing it. These kinds of films can really stick with a person, even when they're painful to watch. And the opening comes from The Shootist, which was meant as a cap on John Wayne's career. It opens with a montage of early Wayne films, meant to be the history of the character he was playing in that one film.