失恋排行榜

罗伯（约翰·库萨克 John Cusack 饰）是个音乐狂热爱好者，他经营着一家唱片店，店里的两名店员迪克和伯利都是音乐爱好者。一天，罗伯的女友罗拉（艾本·叶尤 Iben Hjejle 饰）跟他提出分手，他甚至搞不清楚原因。为此他做起自己的“失恋排行榜”，回顾一路以来失败的恋爱。他发现自己总是充当被甩的一方，于是他决定重新联系这些前女友，询问她们当初选择分手的原因。 　　与此同时，罗拉因为要搬出罗伯的住处而与他一直保持着联系。一次，罗伯从罗拉的朋友口中得知，罗拉居然开始和住在自家楼上的伊安（蒂姆·罗宾斯 Tim Robbins 饰）约会。这让罗伯大受打击，他开始不停地打电话骚扰罗拉和伊安，在他们楼下徘徊。终于有一天，转机到了，罗拉告诉罗伯，她父亲去世了……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 an 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 a 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 no where, 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.