How to Keep a One-Room Play Interesting
It is very difficult to keep a film (and probably moreso a play) interesting for more than an hour if there is essentially one scene taking place in one room. Even with an interesting plot and seemingly interesting characters, the viewer may still eventually feel exhausted by the whole effort. Fortunately for the viewer and for the genre, this movie does a better job than most of keeping it intriguing.
The first thing that director Richard Linklater does right is the employment of great actors: Ethan Hawke (fourth collaboration), Uma Thurman, and Robert Sean Leonard. The second strength of film, probably a credit to the quality of the script, is that the winding nature of the conversations across time and subjects, gradually revealing more about the characters and changing your perception of them, keeps the whole project interesting. This could have easily become a tiring exercise in "independent film" gone wrong, but the marraige of talented people with a good script makes this a worthwhile effort. It's not out to give you straightforward answers about anything but does make you think about first impressions and of what people are made (that was a desperate attempt not to end the sentence with a preposition).
Another Richard Linklater film I liked much more: Waking Life. Another Richard Linklater film I liked much less: SubUrbia.
Bottom line: A 90-minute conversation that's definitely worth seeing.