During the restaurant scene when a woman offers to sleep with Max, he turns to her and says "How you doin'?", an obvious nod to his work on the show "F·r·i·e·n·d·s", where this a recurring line.
Schwimmer received an executive producer credit on this picture as he contributed many notes for the screenplay overall--the idea to make his character a sportscaster, the location of Chicago and such.
The film is supposedly inspired by a short story, "The Tale of Impertinent Curiosity", included in Cervantes' "Don Quixote". Cervantes's short story, however, is a tragedy.
The band featured in some of the scenes shot at the Green Mill is known as the Mighty Blue Kings.
David Schwimmer's character, Max Abbitt, was named after the show's production accountant David Abbitt, who the producers felt bore a physical resemblance to Schwimmer.
The role of Max Abbitt was specifically written and designed for David Schwimmer (who is friends with writer/director Doug Ellin) as he wanted to break away from his "Friends" character on the big screen.