Timothy Hutton portrays Willie Conway, a young piano player struggling with commitment and facing relationship dilemmas.
Matt Dillon plays Tommy 'Birdman' Rowland, a charming but immature individual who is reluctant to grow up and settle down.
Noah Emmerich takes on the role of Michael 'Mo' Morris, one of Willie's friends who is preparing for his upcoming wedding.
Annabeth Gish portrays Tracy Stover, Willie's high school sweetheart, who is now married and has moved on with her life.
Lauren Holly plays Darian Smalls, a beautiful and enigmatic woman who captures the attention of many in the town.
Uma Thurman embodies the character of Andera, a sophisticated and attractive woman who works at the local bar.
Mira Sorvino takes on the role of Sharon Cassidy, an old classmate who has become a successful and ambitious lawyer.
Michael Rapaport portrays Paul Kirkwood, one of Willie's friends struggling with his love life and career choices.
Rosie O'Donnell plays Gina Barrisano, a blunt and outspoken friend who offers advice and humor in various situations.
Pruitt Taylor Vince embodies Stanley 'Stinky' Womack, a quirky and lovable character dealing with his own personal challenges.
Max Perlich portrays Kev, a friend of Willie's who adds comedic moments to the group dynamic.
Martha Plimpton takes on the role of Jan, a local waitress and friend who provides a familiar presence in Willie's hometown.
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