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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.
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.
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.
Noah Emmerich and Natalie Portman would go on to play husband-wife in Jane Got a Gun (2015) twenty years later.
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".
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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The scene where the cast breaks into a rendition of "Sweet Caroline" in a fictitious, small-town New England gin mill predates the tradition started in 1997 by the Boston Red Sox Fenway Park faithful who have joined in the singing of the Neil Diamond classic ever since. The film's tagline, "Good times never seemed so good," is taken from that song's chorus.
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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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Matt Dillon's character stays home during the reunion to watch Rich Man, Poor Man (1976) and he mentions how there was never a scarier villain than 'Falconetti,' played by William Smith. Dillon had appeared in two movies with William Smith, The Outsiders (1983) and Rumble Fish (1983). In both movies, he played the antagonist to Smith's character.
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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 film cast includes three Oscar winners: Natalie Portman, Timothy Hutton and Mira Sorvino; and two Oscar nominees: Matt Dillon and Uma Thurman.
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The Afghan Whigs make a cameo appearance in the film. Lead singer Greg Dulli was a good friend of director Ted Demme.
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Scott Rosenberg's TV series October Road (2007) is largely a follow-up to this film.
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Scott Rosenberg rattled off the script in just five days.
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Matt Dillon and Max Perlich also appeared in Drugstore Cowboy (1989).
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Uma Thurman and Natalie Portman would go on to star in comic book/superhero movies. Thurman in Batman & Robin (1997) and Portman in Thor (2011) and Thor: The Dark World (2013).
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Michael Rapaport and Mira Sorvino previously worked together in Mighty Aphrodite (1995), the film which won Sorvino the Academy Award for Best Supporting Actress. Both of them would also co-star with Lisa Kudrow - Rapport on Friends (1994) as Phoebe's cop boyfriend Gary and Sorvino on Romy and Michele'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 Léon: The Professional (1994).
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