Winona Ryder plays Lelaina Pierce, an aspiring filmmaker who struggles with relationships and the pressures of adulthood.
Ethan Hawke portrays Troy Dyer, a slacker and musician who becomes romantically involved with Lelaina.
Janeane Garofalo plays Vickie Miner, Lelaina's friend who deals with her own personal issues while offering support.
Steve Zahn portrays Sammy Gray, a close friend of Lelaina who provides comic relief and insight into their social lives.
Ben Stiller plays Michael Grates, a successful television producer who expresses interest in Lelaina.
Swoosie Kurtz plays Charlane McGregor, Lelaina's mother who offers guidance throughout her daughter's journey.
Harry O'Reilly portrays Wes McGregor, Lelaina's father who has his own views about life and responsibilities.
Susan Norfleet plays Helen Anne Pierce, Lelaina's aunt who plays a supporting role in her life.
Joe Don Baker portrays Tom Pierce, Lelaina's estranged father who adds to her complex family dynamics.
Renée Zellweger plays Tami, a character who interacts with the main group and adds depth to their social circle.
James Rothenberg portrays Rick, a minor character in the film who interacts with the main cast.
John Mahoney plays Grant Gubler, a character who further develops the storyline revolving around the main characters.
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