The movie follows Rob Gordon, a self-identified music enthusiast played by John Cusack, who grapples with his inability to connect with women. After being unceremoniously dumped by his girlfriend Laura (Iben Hjejle), he decides to reach out to some of his past love interests to unpack his recurring relationship issues.
Rob reflects on his top five breakups, starting with Allison Ashmore, who, at the age of 14, invited him for a series of passionate kissing sessions over three days but flitted to another boy on the fourth day. Then there’s Penny Hardwick, whom he dumped in college because she was so committed to not having sex with him. Next is Charlie Nicholson, a captivating college sweetheart whose allure made Rob insecure; she ultimately left him for one of her bandmates, causing him to spiral into drinking and academic failure. Sarah, another former flame, was in a similar rebound situation with Rob but moved on to someone else, and finally, the much-referenced Laura—the heart of Rob's turmoil—whom he cheated on while she was pregnant, leading to an inevitable abortion and a bank of unresolved guilt.
During his days working at Championship Vinyl, Rob discusses his life and music with his loyal, albeit unorthodox, employees—Dick (Todd Louiso) and Barry (Jack Black). Known as the "musical moron twins," they produce various "top five" lists to pass the time and occasionally sell records while critiquing their customers' music knowledge.
As Rob makes calls to these past relationships to gain insights into his failures, unexpected truths surface. After learning that Allison quickly married after him, he confronts Penny, who shares her regrets about their relationship, and he discovers Sarah is still single, expressing a wish to reconcile. Meanwhile, Rob grapples with his feelings about Laura, who is now seeing Ian, the man living above him, leading to an emotional climax where Laura reveals she has slept with him, deepening Rob's heartbreak.
Obsessed, Rob pesters Ian through frequent payphone calls, attempting to disrupt their time together. A chance encounter at Laura’s father's funeral brings them closer, where Rob realizes his lack of commitment has cost him dearly. This cathartic moment allows him to reconnect with Laura, leading to a hopeful reconciliation, even as he navigates new emotional territory with another woman during a music magazine interview.
Throughout, Rob maintains a humorous yet poignant outlook on love, heartbreak, and the power of music, ultimately discovering the importance of communication in his relationships. As the film concludes, the balance of feelings between Rob and Laura shifts, culminating in their evolving relationship dynamic, backed by the backdrop of musical growth and personal reflection.
