I generally prefer films with complex plots, and i also generally recoil at the very concept of a comedy-drama. But The Outside Story is both these things, but also very good.
Charles is boring, lame Newyorker. He is content with sitting at home doing nothing, he has a stuffy job that he takes way too seriously and it bums him out, and he is generally not fun to be around. Charles' girlfriend Isha has unfortunately come to the same conclusion, and at the very start of the film, she has left him. To make things worse, in a moment of absentmindedness, Charles also locks himself out of his Brooklyn apartment.
No keys, a dying phone battery, no money, no shoes, in order to survive the day, without starving, getting arrested or soiling himself, Charles has to urgently learn how to Deal With People.
.. everything about this film is done the way *I* expect a film to be done; well written, superbly acted, interesting characters that spring out of the setting rather than sticking out, good pacing, good photography, good soundtrack, spotless dialogue, and TOS works both as a comedy, but also as a drama.
I would happily recommend this film. The plot is simple, but do not let that deceive you - there is plenty of enjoyment to be had here.
My vote: 7.5/10 - a lovely, well made film that delivers more than expected.