Quintessential Chicagoan John Cusack counts down his top five break-ups in this music driven comedic drama based on Nick Hornby’s 1995 novel.

When independent record store owner Rob Gordon gets dumped by his girlfriend, he launches into the one thing that makes him feel secure: lists. As he lists his top five break-ups of all time, including the current one, he comes to realize that memory isn’t always a reliable resource and perhaps the answer to his problems lies in growing up. Set in the Wicker Park section of Chicago at the height of the late 1990s indie music scene, High Fidelity captures the slacker-ness of the time through the beautiful pain of losing someone you love. It’s like John Cusack becomes Lloyd Dobbler for the2000s. Also, Jack Black is stunningly brilliant in his role of the abrasive, loud-mouth, offensive record store employee.