Charles is the owner of a camera and photograph developing store (important to note that the film was made in the late 90's); he lives a lonely life where he shuns most interactions and spends his evening sitting in a bowl of ice cream while music blares on his record player. Florence is an old woman who spends her days chatting with friend Tina but is treated badly by her domineering, gambler husband Lester. These two lives move forward but will eventually intertwine.
Although I don't think he is perfect, I do find that Louis CK is a very interesting comedian and when he offered this old film for $5 recently, I decided to give it a go. The film is presented in black/white with a style and content that occasionally suggests a much older film than the late 90's but the humor is certainly nothing but modern. If the plot sounds deliberately odd then it is right because the whole film has this very odd air to it of stilted awkwardness and oddity; if you are into that then you'll love this film a great deal but for me, even as one who likes CK, I mostly thought it didn't work. Too often the silences and stillness didn't work and the lack of me being amused left the material exposed. That said there are lots of moments that work but they are mostly where energy is brought into the film, or odd images are nicely presented.
So for example the energy brought by Smoove and Shapiro is really fun, while some cool "out of the blue" stuff is oddly enjoyable – such as the boy Clean. Sadly though too much of it left me cold and just felt too out there for me to be able to connect with. If you're in the mood and get on the same wavelength then I guess you'll have more bits that work than I did – but this film really is a very tight wavelength.