Roger Ebert claimed this was the best movie of 1987 in his round up of 1988. David Mamet's first outing as a film director, which shows as his lead (and wife of that moment?) Lindsay Crouse delivers her lines in theatrical style. It's something of a modern noir, shot like Scorcese's After Hours amongst others. As with most of what I remember from Mamet it's long on the con and short on pretty much everything else; also there's been too many slicker efforts in the meantime for this to endure. It's always a shame when the Chekhovian device, here introduced very early on, actually goes off and yet doesn't resolve anything. William H. Macy was young once. Joe Mantegna leads the cons before he took his place in The Godfather Part III.
Ebert dug it at the time and again in 1999, which I put it down to them both being big Chicago fish. Vincent Canby got right into it too, but comedy?