High Fidelity (2000)

Thirtysomething John Cusack owns a record shop that he runs with his friends Barry and Dick. John just found out that his girl, Iben Hjejle, is dating the upstairs-neighbor dork--played ably by Tim Robbins. At first, John can’t say anything and feels he’d be better off dead. But he finally gets off his ass and does something: He goes back and asks all his old girlfriends where he went wrong with them. Funny that Ione Skye never gets a call? John also tries to compile top-ten lists of every great song and make the perfect mix tape, while his record shop pals drive away all the paying customers--but that’s not important right now. Johnny rockets through relationship rehashes with a bevy of hotties including Lisa Bonet, Catherine Zeta-Jones, Lili Taylor and Joelle Carter. So where exactly did he go wrong? That’s one hell of a babe-alicious statsheet!