Beautiful Girls

Ted Demme told Timothy Hutton to kiss Natalie Portman on the cheek. Hutton did not know about it beforehand, so his reaction in the film was spontaneous.

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The film was inspired by screenwriter Scott Rosenberg's experiences while returning to Needham, Massachusetts. During what he claimed was his hometown's worst winter, he was anxiously waiting to see whether his script for Con Air (1997) would be produced and had grown tired of writing action films. Rosenberg said there was more action because his friends did not want to admit they had reached 30 or were having commitment problems, and this formed the basis of Beautiful Girls (1996).

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Ted Demme had the cast come to Minneapolis and live together for two to three weeks so they could bond.

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Tony Scott turned down the chance to direct because he felt he could not do justice to Scott Rosenberg's script, which put characterization and dialogue ahead of dramatic events.

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Scott Rosenberg's TV series October Road (2007) is largely a continuation of this film.

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The scene in which the actors perform a version of "Sweet Caroline" at a fictional candy factory in a small New England town predates the tradition started in 1997 by Boston Red Sox Fenway Park loyalists joining in on the Neil Diamond classic. The film's tagline, "Good times never seemed so good," is taken from the song's chorus.

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Wanting to portray the fictional town like any working-class town in America, Ted Demme drew inspiration from The Deer Hunter (1978) and showed the film to the cast and crew. Demme said the first third of the film depicted true friendship.

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Ben Stiller was offered the chance to direct and star in the film; although he liked the script very much, he did not want to direct it and turned it down.

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Noah Emmerich and Natalie Portman would go on to play husband and wife twenty years later in Jane Got a Gun (2015).

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The only actors in the main cast who were the same age as their characters were Mira Sorvino, Max Perlich and Anne Bobby. Although the characters played by Timothy Hutton and Michael Rapaport were expected to be the same age, in real life Hutton is ten years older than Rapaport.

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The Afghan Whigs play a small role in the film. Lead singer Greg Dulli was a good friend of director Ted Demme.

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In 2020, Natalie Portman called for an end to the sexualization of young actors and characters because it can cause serious psychological problems. Citing her role in this film, in which she played a 13-year-old girl involved with a man older than herself, the actress said it made her feel the need to camouflage her sexuality in real life. "Being sexualized as a child, I think, took away my own sexuality, because it made me afraid. But at that age, you do have your own sexuality, you have your own desire, and you want to explore things, and you want to be open. But when older men are interested and you say 'No, no, no, no,' you don't feel safe." Portman explained that her way of dealing with this discomfort was to turn down roles considered sexual in order to have some control over her life. "During my teenage years I was saying, 'I don't want to see any love scene or sex scene.' I started choosing the parts that were less sexy, because it worried me about how I was perceived and how safe I felt.

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Although the film's posters depict her as a blonde, Lauren Holly is clearly a redhead in the film.

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Scott Rosenberg completed the script in only five days.

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Matt Dillon's character stays home during the gathering to watch Rich Man, Poor Man (1976) and mentions that a villain more terrifying than 'Falconetti,' played by William Smith, has never been found. Dillon had appeared with William Smith in two films, The Outsiders (1983) and Rumble Fish (1983). In both films, Smith played the enemy of Dillon's character.

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The film's 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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When Uma Thurman leaves the icehouse with Timothy Hutton, she has to duck her head as she goes through the door, but she actually hits her head on the side of the door!

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Mira Sorvino and Michael Rapaport had previously appeared a year earlier in Woody Allen's Mighty Aphrodite (1995); Mira won the Oscar for that film.

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At the time of the film's release, Lauren Holly was completing a four-year run on another small-town drama, Picket Fences (1992).

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One of the photos on this page shows Timothy Hutton and Lauren Holly together in a scene, although they never actually shared a scene in the film.

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Matt Dillon and Max Perlich also appeared in Drugstore Cowboy (1989).

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In the meeting there is a scene where Rosie O'Donnell's character tells Annabeth Gish's character that she resembles Ally Sheedy in The Breakfast Club (1985). She then says it was the film with the Estevez brothers. However, while Emilio Estevez was in the film, Charlie Sheen was not. Charlie played a character in John Hughes's Ferris Bueller's Day Off (1986).

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Michael Rapaport and Mira Sorvino had previously worked together on Mighty Aphrodite (1995), which won Sorvino the Academy Award for Best Supporting Actress. Both would also appear alongside Lisa Kudrow — Rapaport as Phoebe's police officer boyfriend Gary on Friends (1994), and Sorvino in Romy and Michele's High School Reunion (1997).

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Sharon's doorbell has a delay. Tommy leans in to ring the doorbell, but you don't hear it ring right away.

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Uma Thurman and Natalie Portman would go on to appear in comic book/superhero films: Thurman in Batman & Robin (1997), and Portman in Thor (2011) and Thor: The Dark World (2013).

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Paul (Michael Rapaport) has a dog named Elle Macpherson, after the supermodel. Uma Thurman (Andera) later appeared alongside Elle Macpherson in Batman & Robin (1997), in which both women compete for the love of Bruce Wayne/Batman (George Clooney).

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Richard Bright and Adam LeFevre appeared in The Ref (1994).

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