I recently rewatched Ted Demme‘s (R.I.P.) Beautiful Girls as I mentally prepared myself for my 20-year high school reunion which is happening this weekend. Outside of Grosse Pointe Blank, I don’t think there is a better film that captures the angst and uncertainty about one’s life and what one has achieved up to a point in light of returning home to meet with old friends to celebrate times past, present and those that might occur in the future.

The story centers on Willie Conway (Timothy Hutton) who himself is returning home for his 10-year high school reunion to his family home in Knightsridge, Massachusetts. His father (Richard Bright) has yet to reconcile the death of his wife, spending his days in front of the TV watching golf and his brother Bobby (David Arquette) is as lost, doing nothing with his life that we can see. Willie is in the same boat, though. He is a piano player who plays for chump change in New York City. He is dating a lovely lawyer named Tracy (Annabeth Gish), but isn’t sure he wants to commit. So he comes home to think his life over, see his old friends and to try and find some perspective. Wrong move.

When he arrives in Knightsridge via Greyhound, his buddy Moe (Noah Emmerich) picks him up. Moe seems to have it all worked out – he got the wife, two kids, house and a great job. He sets the standard, the societal expectation, for what Willie and his friends were expected to become in the years since they left school. However, we quickly see this isn’t the case.

His buddy Paul (Michael Rapaport) is the one who is most off his rocker. Having been dating his girlfriend Jan (Martha Plimpton) for seven years, he like many men, is afraid of commitment. So she does what any self-respecting woman should do in similar circumstances – dump his ass. He can’t get past this, not seeing the error of his ways. He is obsessed with models (he has a dog named Elle MacPherson) and thinks that only through a model that he can find true happiness. See for yourself:

Guy is looney tunes, but it’s likely the inspiration for the title of the film and it works for the character.

Tommy is just as fucked up as Paul. He has a girlfriend, Sharon (Mira Sorvino), but consistently cheats on her with his married ex-high school flame, Darian Smalls (Lauren Holly). Trying to relive the past when he and Darian were the hottest couple in school, he is slowly destroying Sharon, who has adopted an eating disorder as her way to keep Tommy around.

That leaves us with Kev (Max Perlich), easily my favorite character in the film, albeit the one who has the least amount of screen time. If I had to be a character in this film, it would be him. Kev is the conscience of the group, balancing out the craziness of Paul, the sliminess of Tommy and the ambivalence of Willie.

Together these five guys represent a pretty wide spectrum of personalities and a group that many people can probably identify with having been a part of or knowing.

So as Willie navigates these relationships and tries to glean what he can from them to help out in his own situation, he meets Marty (Natalie Portman), the 13-year old girl who lives next door. They strike up an instant rapport and throughout the film flirt, getting to know one another. Marty is the antidote to his group of friends – a level-headed, thought-provoking young lady who gives him much more clarity in the short talks they have than the weeks he spends with his friends. But she too has an agenda:

So Willie is left to figure out on his own what he wants from his life as Paul’s relationship falls apart, as Tommy tries to mend fences with Sharon and as Moe tries to keep his cool when Darian’s husband (Sam Robards) exacts revenge on Tommy for the years of fucking around with his wife. So even though the reason they are all together is the reunion, none of them ever make it. Their past which they are there to celebrate directly affects their present, making it impossible to embrace until those past indiscretions are rectified.

While all of this seems heavy, and there are heavy parts to this film, it is also very funny. Rosie O’Donnell delivers one of the all-time greatest monologues I’ve ever seen chastising Willie, Tommy and Paul for their (and all men’s) obsession with fake female beauty and their overall piggishness, which is confirmed time and again throughout this film. Check it out:

Uma Thurman‘s turn as Andera, a true beautiful girl, is also quite wonderful. She outduels the boys at every turn and shows the boys for what they really are…boys.

And who can forget the “Sweet Caroline” scene, right? Just a total classic moment and one of the great musical interludes in recent memory.

This is such a fun movie, one I truly love and one that is very pertinent to me at this time. I look forward to going home this weekend and reviving old friendships, reliving good times and making great new memories – something that these characters also do.

If you haven’t seen this one, do yourself a favor and check it out.

And I will say this, it ends on such a great interaction between Kev and Willie. I wish I could find a damn clip, but alas I can’t. The still below gives you the gist of the exchange, and I can’t explain why it hits me so hard, but it does.

“Stay cool. Stay cool forever.” Damn. Gets me every time.

Here’s the trailer: