Michael Morris, Jr (as Trent Nicholas Thompson 'TNT')
Nicole Ranallo
Cheryl Morris
Joyce Lacey
Reunion Classmate #1
Matthew Nathan Castens
Reunion Classmate #2
Anne W. Erickson
Coffee Shop Waitress
Oliver Osterberg
Drinker #1 (as Ollie Osterberg)
Sterling Robson
Drinker #2
Edward Kaspszak
Drinker #3
John Scurti
Ticket Agent
Herbie Ade
Bar Owner (as Herbert Ade)
Ben Gooding
Customer
Frank Anello
Irv
Lucky the Saint Bernard
Elle MacPherson
Tammara Melloy
Bowler (uncredited)
Lori J. Ness
Women on the Street (uncredited)
Rachel Oliva
High School Alumna (uncredited)
Tomas Settell
Male Nurse (uncredited)
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Trivia
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).
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".
Gina mentions to Tracy that she looks like Ally Sheedy from The Breakfast Club with the Estevez Brothers. Ally Sheedy and Emilio Estevez were in Breakfast Club but his brother Charlie Sheen (Carlos Irwin Estevez) was not.