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 "Friends", where this a recurring line.
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.
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 band featured in some of the scenes shot at the Green Mill is known as the Mighty Blue Kings.