Maybe the most impressive thing about Grosse Pointe Blank is that it's almost as hip as it thinks it is: quirky, subversive, sporadically funny, vaguely intellectual (for me, the biggest laugh of the film came with Dan Aykroyd's character's declaration "workers of the world unite!"), wired into pop culture (dig the 80s soundtrack), suitably 'meta' (note the Pulp Fiction cardboard cutouts...and then wonder about the inane dialogue of the two dorky government assassin-wannabe types, one black, one white), with a good ear for dialogue and a dab hand with satire (the scenes in which Martin Blank does small talk are so excruciating because they're only a small step - and sometimes not even a small step - away from how these things actually do go), and basically warm-hearted and feel-good.
As to the acting, John Cusack provides a good centre and Minnie Driver, as the other part of the 'romantic comedy' element of the pic, fits well with him, and both have nice characters to play with; also, the supporting roles are well filled (Joan Cusack is a particular delight, especially in her final scene). Alack, however, all told the film is just slightly off-key - the pacing's a bit weird, and the up-and-downness, while most likely intended, prevents the whole from cohering into anything in particular. The touch with which it was conceived and made isn't as deft as it might have been, with the result that while we can sometimes tell what the film is trying to do, at the same time we become aware that it has fallen short in that attempt (eg, with the violence, and more generally with the sense that it's striving for 'black comedy with a heart' and only getting halfway there). Still, not a bad little number, and if it's a bit of a mess, well, it's still a worthy attempt with some neat elements.