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Beautiful Girls (1996) Poster

Trivia

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The movie was inspired by the experiences of screenwriter Scott Rosenberg when returning home to Needham, Massachusetts. During what he claimed was the worst winter for his hometown, he was waiting to see if his script Con Air (1997) was going to be produced and was getting fed up with writing action movies. Rosenberg cited that there was more action happening with his friends not wanting to accept that they were turning 30 or had commitment issues, which became the basis for Beautiful Girls (1996).
Ted Demme had the cast come to Minneapolis and live with each other for 2-3 weeks so they could bond.
Tony Scott turned down a chance to direct, because he felt he couldn't do justice to Scott Rosenberg's script, which placed characterization and dialogue above dramatic event.
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Wanting to depict the fictional town as being like any other working class town in America, Ted Demme drew inspiration from The Deer Hunter (1978) and had the film screened for the cast and crew. Demme cited the first third of that film as depicting real friendship.
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Paul's monologue to Will, "A beautiful girl can make you dizzy, like you've been drinking Jack and Coke all morning. She can make you feel high full of the single greatest commodity known to man - promise. Promise of a better day. Promise of a greater hope. Promise of a new tomorrow. This particular aura can be found in the gait of a beautiful girl. In her smile, in her soul, the way she makes every rotten little thing about life seem like it's going to be okay." is in the intro to the demo version of a Taking Back Sunday song called, "Great Romances of the Twentieth Century".
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Matt Dillon's character refers to "Falconetti" from Rich Man, Poor Man (1976) as being a terrifying villain. In The Outsiders (1983), Matt Dillon's character was killed by a character played by William Smith, who also played "Falconetti".
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Noah Emmerich and Natalie Portman would go on to play husband-wife in Jane Got A Gun (2016) twenty years later.
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Gina opens up a Penthouse magazine and uses the centerfold to criticize the media's unrealistic portrayal of women. The woman in the centerfold is Lynn Turner from the March 1995 issue of Penthouse.
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Although her character Marty is 13 in the movie. Natalie Portman was 15 when the film was released.
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According to Leslie Mann, who auditioned for a role in the film, James L. Brooks was interested in directing the film at one point.
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The only actors in the principal cast who were the same ages as their characters were Mira Sorvino, Max Perlich and Anne Bobby. Although the characters played by Timothy Hutton and Michael Rapaport are supposed to be the same age, in real life Hutton is more than ten years older than Rapaport.
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Uma Thurman and Natalie Portman would go on to star in comic book/superhero movies. Thurman in Batman & Robin and Portman in Thor (2011) and Thor: The Dark World (2013).
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Michael Rappaport and Mira Sorvino previously worked together in Woody Allen's Mighty Aphrodite (1995), the film Sorvino won the Best Suporting Actress Oscar for, one year prior. On top of that, two would go on to co-star with Lisa Kudrow. Rapport on Friends as Phoebe's cop boyfriend Gary and Sorvino on Romy and Michelle's High School Reunion (1997).
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Spoilers 

The trivia items below may give away important plot points.

Ted Demme told Timothy Hutton to kiss Natalie Portman on the cheek. She did not know it so her reaction in the film is spontaneous.
At the end of the film Paul (Michael Rapaport) refers to Marty (Natalie Portman) as "the local neighbourhood Lolita." Ironically, Natalie Portman plays an arguably Lolita-esqué character in Leon the Professional.
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