Grosse Point Blank (1997)

One of the things I love about this movie is that Martin Blank (John Cusack) always tells everyone who asks that he is a professional killer. Everyone asks him where he has been since high school, and he just tells them. They all assume that he's making a joke.
Another thing I love about this movie is the character of Marcella (Joan Cusack). She has so got her shit together. When she has the munitions dealer on one line and her sister on the other and just goes back and forth betwen cussing out the former and explaining a soup base to the latter, it's comic genius.
I can keep going with reasons why I love this film, but they all boil down to character's quirky behaviors. Whether it be the neurotic psychologist who may have been just fine before meeting Martin, or Grocer taking his experimental drugs and trying to unionize the professional killers. Or how about the classmates of Martin? Paul, the pot smoking real estate agent, or Bob the coke snorting car salesman or Terry the private security officer, or how about Tanya the neck-brace-wearing-near-death-experience-having girl who wants to dance with Martin? The only one that isn't terribly quirky is Debi Newberry (Minnie Driver), but who seems to be going through some kind of self-imposed therapy as an on-air personality for the local radio station.
The one thing that I don't like about this movie is that they are attending their ten year reunion. I can buy how much the characters have changed, but I have an issue with the actors, all of whom are older than 28. When this film first came out, I remember thinking this. It still holds true 15 years later. I was 24 when this came out and most of these actors had been doing their thing professionally since I was in junior high. But, I guess having it be a 15 year reunion would be weird, and a 20 reunion would have meant that some of the classmates had gotten together earlier. Also, not a criticism of the film as much as it is of my high school, but the music my school was listening to was not near as good. Not even close. Our soundtrack would have been all AC-DC, Metallica, Billy Idol and Billy Ray Cyrus.

Grosse Point Blank on IMDb