Paul: So you're the little neighborhood Lolita.
Marty: So you're the alcoholic high school buddy shit for brains.

With a stellar cast of talented character actors, Ted Demme's "Beautiful Girls" is a truly unappreciated gem that gives a ponderous story along with a hefty slice of life that American audiences will appreciate; with the characters in "beautiful Girls" there are an array of odd and unusual characters that could only be found in a screenplay by John Waters and it's just as good with writer Scott Rosenberg who supplies something badly missing from today's films: great characters, a deep story, and a wry screenplay you only dream of. We get a portrait of a man named Willie Conway, a man at the crossroads of his life who returns to his hometown to re-unite with his gang of buddies and discovers they haven't moved on and are at a crossroads as he is. He begins to notice they're the exact same people they were when he left and begins to search for an answer to the questions he's be asking. The film is aptly titled because every male character in the film gets some idea of what a beautiful girl is in every shape and form, and they're in the film proving as examples to what many types a beautiful girl can be in the form of, ala Rosie O'Donnell, Natalie Portman, Mira Sorvino, and Uma Thurman.

Tommy Rowland who is questioning whether he loves his wife or not and wants to get married to her gets his depiction of a beautiful girl in the form of the neighborhood girl thirteen year old Marty (Not short for Martha but for Martin her grandfather) played by Natalie Portman who is too mature and smart for her age often quoting Shakespeare and discovers Tommy's reason for coming home by simply guessing. The two instantly form a flirtatious friendship and soon a crush develops. Despite excellent chemistry, teen heartthrob Natalie Portman steals all the scenes with Timothy Hutton and lights up the movie in each and every one of her scenes with her beauty, charm and utter exuberance. The chemistry between the two as they casually flirt may look inappropriate if handled wrong, but the flirtatious relationship between them is charming and engrossing noticing how Portman's character instantly forms a crush on Hutton's character and in his own way he forms a crush on her. But she is a symbol of his childhood, the goal he could never achieve, and the life he left behind that he didn't want to let go of and by him letting go in the end, he manages to leave his past behind.

Portman's character is a symbol of someone who will grow up to be something amazing but refuses to like anyone else in the town but gains an infatuation with Hutton's character because he managed to leave the town behind. He realizes he has a crush on her but can never act upon his feeling's lest he be even more isolated from the people within his hometown. Many of the people in the town are as still as water, they're not moving forward in life and they're always lingering in the past but fear of ending up in the inevitable, as simple people with no real contribution. Michael Rappaport's character Paul is a man who is afraid to move onto the next pinnacle of his relationship with his seven year girlfriend Jan (Martha Plimpton), but gets jealous thinking she's with another man never realizing all she wants is to get married, so he asks her but out of fear of losing her, not out of commitment, Matt Dillon's character Tommy is a man whose managed to let go of the past but refuses to move on into life because he's afraid of losing the magic life and love have to offer him, so he jumps from one woman to another and subconsciously purposely ruins relationships.

One of the buddies is a man who has become a simple family man but is looked down upon by his other friends who never realize they actually envy him. The female cast is supplied with some incredible actresses including Mira Sorvino, AnnaBeth Gish, and Uma Thurman, but the two most intriguing characters of the film are Lauren Holly who plays Darian, a beautiful ex-prom queen who's basically in a rut with children and a husband whom she claims to love but flirts with every man in town especially Tommy, and then there's Rosie O'Donnell's character Gina who's possibly the most down to earth character in the film played with much skill by O'Donnell who gives an excellent monologue on men and how they're more attracted to fake women on magazines than real women who are right in their own backyard. In the end, there's people that move on, people that stay where they are whether they're content with it or not, and people who will never change despite the lives they lead, but we leave with a sense of satisfaction and want to see much more of these people.

The film does tend to feel too unresolved in the climax as all the characters situations are never really drawn to a close or resolved in the proper way. And as inappropriate as it may sound, the chemistry between Portman and Hutton's character was so good that it left me hoping they would inevitably get together despite their massive age difference, but alas it left me disappointed.

This is a charming, truly memorable, fascinating and entertaining dramedy with excellent performances from an all-star cast of talented actors whom pull in great performances.

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