Its story follows New York jazz pianist Willie Conway, as he heads back to his hometown of Knight's Ridge, Massachusetts for his high school reunion, where he finds his friends evaluating their lives and relationships.

It stars Matt Dillon, Noah Emmerich, Lauren Holly, Timothy Hutton, Rosie O'Donnell, Martha Plimpton, Natalie Portman, Michael Rapaport, Mira Sorvino and Uma Thurman.

[1] New York jazz pianist Willie returns to his hometown of Knight's Ridge, Massachusetts for his 10-year high school reunion, staying with his widower father and younger brother.

Willie reunites with three old friends: Mo is a successful family man, while Paul and Tommy, who own a snowplowing business, have relationship issues.

The outspoken Gina advises her to break up with Tommy, but Sharon tries to salvage the relationship by planning a surprise birthday party.

Darian shows up at Tommy's surprise party drunk and openly tries to seduce him, causing Sharon to leave, heartbroken.

Additional minor roles were played by Kristen Rossmore as Steve and Darian's daughter Kristen; Camille D'Ambrose as Sharon's mother; Martin Ruben as Jan's restaurant boss Chip; Allison Levine as a waitress; Earl R. Burt as a bartender; Trent Nicholas Thompson and Nicole Ranallo as Mo and Sarah's children Michael and Cheryl; Joyce Lacey and Matthew Nathen Castens as classmates at the reunion; Ollie Osterberg, Sterling Robson, and Edward Kaspszak as Steve's friends who beat up Tommy; Herbert Ade as a bar owner; Ben Gooding as a customer; and Frank Anello as Irv.

Screenwriter Scott Rosenberg was living in Needham, Massachusetts, waiting to see if Disney would use his script for Con Air.

Filming took place in the Twin Cities Metro Area communities of Edina, Marine-on-St. Croix and Stillwater,[5] with Demme wanting to make sure that the setting was a character unto itself.

The site's consensus reads: "A warm, thoughtful dramedy about male insecurity, Beautiful Girls is buoyed by an excellent cast - particularly Natalie Portman in a stunning early role".

"[10] In The Washington Post, Desson Howe praised Natalie Portman's performance: "As a self-described 'old soul' who connects spiritually with Hutton (they're both existential searchers), she's the movie's most poignant and witty presence.

"[11] However, Jack Mathews, in the Los Angeles Times, wrote that the film was "about as much fun as a neighborhood bar on a Tuesday night.

"[12] In her New York Times review Janet Maslin wrote that Natalie Portman got the film's "archest dialogue", and called her "a budding knockout, and scene-stealingly good even in an overly showy role.

[14] Both Beautiful Girls and October Road take place in the fictional Massachusetts town of Knight's Ridge, and have similar characters, jobs, plot lines.