We meet Rob Gordon (John Cusack) just as his girlfriend Laura (Iben Hjejle) is leaving him. Rob's the owner of a specialist record store with two employees, the introverted Dick (Todd Louiso) and the wildly extrovert Barry (Jack Black). They are all obsessive music buffs who compare top fives on any topic. Rob starts making his own top five lists - including the top five rejections from women he's had in his life - and Laura doesn't make the list. While becoming vaguely interested in a singer - Rob decides to revisit his top five rejections in an effort to understand what goes wrong with him and women...
Working from the wonderfully honest base of Hornby's novel writers and co-producers John Cusack, D.V. DeVincentis and Steve Pink with Scott Rosenberg have transposed the novel so successfully to Chicago that it seems always to have belonged there. This is obviously a labour of love for all of them. Cusack is a marvellous performer and he's wonderfully wry, sleazy, pathetic and sympathetic as Rob. Jack Black is a dynamo as Barry and Todd Louiso is a perfect counterfoil to him. Iben Hjejle brings a lovely dignity to Laura. Adding to this perfect mix is Stephen Frears as director, he's brought a lovely rhythm and vision to the film. As a film about males it's amazingly insightful for women. The soundtrack's another great plus. I just adored this film.