The movie comes down to being about sex and relationships. Roger is pretty much a sleazeball who hooks up with women but never seems to have a successful relationship with one. It is billed as a comedy-drama, but it is far more drama than comedy, although there are some humorous moments in it. The writing and acting are great, this was really Eisenberg's first major role (even though it is definitely an independent film and not even close to a blockbuster) and he did a great job playing a pretty conflicted character and Scott played a great womanizer who seemingly had everything he wanted in life but really did not.
For those who get the DVD, the extras are pretty extensive, especially for an independent film. There are multiple commentary tracks on the movie, several making-of features, a walking tour of NY with Jesse Eisenberg, deleted scenes, the trailer, and a "players guide". So, a lot there if you like going through the extras.
Overall, the movie is very good, but probably not for everyone. It has frank discussions about relationships and sex, but there is not much actual sex in it. It also deals with ethical issues like whether to take advantage of someone who is drunk. It definitely has the feel of an independent movie, but it is a very good one. It holds up well even after 20 years and is worth checking out.
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