Cusack co-writes and stars in this film adaptation of the Nick Hornby novel. He plays Rob Gordon, a thirty-something record store owner who tries to understand women and relationships after being dumped by his girlfriend. Co-starring Jack Black, Tim Robbins, Iben Hjejle, and Catherine Zeta-Jones. On accepting the film project:
I could see the geography of each place that Rob would haunt. Wax Trax, Record Exchange… Those were record stores I knew that were exactly like those in the book. That’s one thing about it, but the other is that many young men can identify with Rob’s inner monologue, which is spoken through great, incisive writing.