There are more than 5 reasons to love this movie.

Rating: 9/10 (7 July 2007)

One only has to look at the movies section of the local paper (NOT during the winter Oscar months) to see the astonishingly high number of low-brow movies made specifically for 14-year-olds with Daddy's allowance. So seeing a comedy that is so fresh in its humor, so honest in its views on male romance, and so imperfect its lead protagonist, is about as rare as seeing Halley's comet. It's a moment to savor, for you know it'll be a generation before another like it comes along.
Rob (John Cusack), a thirty-something who owns a record store that "attracts the bare minimum of window shoppers," has just been dumped (yet again) by his current flame Laura (Iben Hjejle) because he hasn't changed or grown up. This sends our immature hero on a journey of self-discovery as to why he can't seem to sustain a relationship, which includes visiting (and re-visiting) all the other girls on his Top 5 list, including (in chronological order) Alison Ashmore, Penny Hardwick, Charlie Nicholson (Catherine Zeta-Jones) and Sara Kendrew (Lili Taylor). All the while, he tries fruitlessly to win back Laura and to grasp why she prefers the company of hippie ex-neighbor Ian "Ray" Raymond (Tim Robbins), in addition to having long talks about music with his two employees, Barry (Jack Black)--imagine a human version of Cartman from "South Park" but with an impeccable taste in music--and quiet Dick (Tod Louiso). Through his journey towards self-discovery, Rob slowly grows up and realizes what relationships are all about.
Rob on page comes off as a self-pitying, adolescent jerk, a challenge for a character-driven comedy/drama. The casting of John Cusack immediately helps the problem, because 1. Cusack is becoming the most automatically charming and lovable star since Cary Grant and 2. as a co-writer of the script, he knows Rob inside, out and backwards. This role is his. And because slowly, we see a boy becoming a man, a common theme of Nick Hornby's books. First Rob wants Laura back simply because his pride is hurt by being dumped, but as time goes by we see that he did truly have affection and love for her, which results in Rob making a list of "Top 5 Things I miss about Luara." There isn't a moment we don't root for him, even when we question his maturity.
The supporting characters provide the movie with a great deal of needed laughs to help ease the at times brutal honesty. Jack Black is a scene-stealer as music snob Barry, a guy so self-righteous he doesn't even give service to a customer who wants to buy "I Just Called to Say I Love You" because it insults his own taste. He's the kind of guy that you would violently assault in reality...if you weren't laughing so hard your stomach feels sore. Had the movie not been saddled with an actor as strong as Cusack, Black would've stolen the show. Tod Louiso is also great as Tod, as quiet as Barry is loud. Tim Robbins must've had so much fun playing the rebound man with a ponytail who inadvertently makes Rob's life a living hell. Joan Cusack, as usual, brings larger-than-life energy to her role as Laura's friend Liz. The only weak link is Iben Hjejle. But it isn't entirely her fault; the movie spends so much time focusing on Rob's dilemma when it should've spent a little time explaining what made Rob fall in love with her in the first place. And against such a great supporting cast, anyone would pale in comparison to Mr. Black.
This movie is, quite simply, the ultimate male chick flick (a dick flick?), one that men can learn from while the women drool over Cusack and both can laugh at the numerous funny and truthful incidents (who HASN'T imagined killing the new flame of an ex?). A great movie if you've been married for 30 years or, more especially, if your relationship can't last longer than a tic-tac. An essential John Cusack role, whose exclusion at awards time is further proof that the 2000 Oscars were a joke. Not since "Say Anything" was Cusack more romantic or lovable. Never again will be more self-confessional. Movies like this don't come out every Friday. What are you waiting for?