– When record store owner Rob Gordon gets dumped by his girlfriend, Laura, because he hasn't changed s..
When record store owner Rob Gordon gets dumped by his girlfriend, Laura, because he hasn't changed since they met, he revisits his top five breakups of all time in an attempt to figure out what went wrong. As Rob seeks out his former lovers to find out why they left, he keeps up his efforts to win Laura back.
31 Mar 2000
Under 17 requires accompanying parent or adult guardian. Contains some adult material. Parents are urged to learn more about the film before taking their young children with them.
Thirty-something Rob Gordon, a former club DJ, owns a not so lucrative used record store in Chicago. He not so much employs Barry and Dick, but rather keeps them around as they showed up at the store one day and never left. All three are vinyl and music snobs, but in different ways. Rob has a penchant for compiling top five lists. The latest of these lists is his top five break-ups, it spurred by the fact that his latest girlfriend, Laura, a lawyer, has just broken up with him. He believed that Laura would be the one who would last, partly as an expectation of where he would be at this stage in his life. Rob admits that there have been a few incidents in their relationship which in and of themselves could be grounds for her to want to break up. To his satisfaction, Laura is not on this top five list. Rob feels a need not only to review the five relationships, which go back as far as middle school when he was twelve, and try to come to terms with why the woman, or girl as the case may be, left him, but also, in the words of Charlie Nicholson, number four on the list, "what it all means" for why he has ended up where he is, which is nowhere, personally or professionally, close to what he envisioned. He also has to come to terms with what it means that Laura has moved on to Ian Raymond, a man for who neither had any respect when they were together.
Nominated for 1 Golden Globe. Another 3 wins & 21 nominations.