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A 1994 romantic Dramedy/Coming of Age saga of four disaffected twentysomething friends from Houston trying to assess the direction of their aimless lives. Winona Ryder stars as Lelaina, a recent college graduate with big dreams of becoming a successful videographer. She shares an apartment with Grunge-rocking slacker Troy (Ethan Hawke), Vickie (Janeane Garofalo), a promiscuous Gap-managing snarker, and Sammy (Steve Zahn), a guy struggling with coming out to his parents, who are facing similar uncertain crossroads in their lives. Leilana meets and dates Michael (Ben Stiller), a yuppie who works for an MTV-like television station.
The film is frequently cited by reviewers as a Generation X parable.
"Miss Pierce, do you have any idea what it means to be a cashier at Wiener Schnitzel?"
- But Not Too Gay: Sammy's first boyfriend Lance is introduced to Lelaina, but not even shown onscreen because Lelaina is too concerned with where Troy is.
- Deadpan Snarker: Vickie.
- Dude Not Ironic: Lelaina's inability to define irony cost her a job.
- Foot Focus: A prolonged closeup of Winona Ryder's bare feet.
- Lowest Common Denominator: In-Universe, Michael's edit of Leilaina's footage.
- Pet Homosexual: Sammy.
- Production Posse: A Ben Stiller film, so his parents and then-girlfriend Janeane Garofalo and make appearances.
- Really Gets Around: Both Troy and Vickie.
- Romantic Runner-Up: Michael's MTVization of Lelaina's documentary does not go over well.
- Take That: To MTV and The Real World.
- The Cast Showoff: Ethan Hawke plays guitar and sings "I'm Nothin'".
- The Nineties: SO much.
- The Slacker: Troy.
- Stylistic Suck: The Show Within a Show at the end of the film, based loosely on the events the characters experienced in the movie.
- Throwing Out the Script: Lelaina pretends to do this -- actually, she's lost her notes and is just reciting platitudes.
- Wrong Guy First