5. Clerks
In case you have never seen the film that launched Kevin Smith's career, you should do that. It is a great example of a young, eager and fresh director putting his money on the line to make his first film, and it all turning out great. The story follows two store clerks, Dante and Randal, and a day in their life. It is hardly a great technical achievement or even well designed in a narrative sense. However, it is a fun, unbroken filmmaker having a good time and telling a series of joke ridden scenes that are genuinely funny. Having Dante and Randal dealing with difficult customers and getting into hyjinks throughout their day could lend itself very well to the musical form. While previous films I have mentioned work for their excess, Clerks could work for entirely opposite reasons. The film is entirely about the mundane life of early twenty-somethings who are lost with what to do in their life, while dreaming of something bigger. Using musical numbers to represent that want to get out of their real reality could actually be pretty interesting. I know a bunch of people who would identify with that.
Songs: "In a row?" "I hate guys. I LOVE WOMEN!" "I'm not even supposed to be here today!" "Umm...37?"