Winona Ryder stars as Lelaina, a recent college graduate with big dreams of becoming a successful videographer. She shares an apartment with Troy (Ethan Hawke), a Grunge-rocking slacker, 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. Lelaina meets and dates Michael (Stiller), a yuppie who works for an MTV-like television station.
The film is frequently cited by reviewers as a Generation X parable.
- Bait-and-Switch Comment:Vickie: [Troy]'s weird, he's strange, he's sloppy, he's a total nightmare for women. (Beat) I can't believe I haven't slept with him yet.
- Betty and Veronica: Troy and Michael, for Lelaina.
- Burger Fool: David Spade's One-Scene Wonder."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.
- The Cast Show Off: Ethan Hawke plays guitar and sings "I'm Nothin'".
- Cool People Rebel Against Authority
- Deadpan Snarker: Vickie.
- Dude, Not Ironic: Lelaina's inability to define irony cost her a job.
- Informed Attribute: Troy allegedly has a genius level IQ, but is unable to offer a remotely accurate definition of irony.
- Lowest Common Denominator: In-Universe, Michael's edit of Lelaina's footage.
- Nice Character, Mean Actor: On stage, Grant Gubler is a Perpetual Smiler TV host of a morning show. Behind the scenes, he is a Grumpy Old Man who dislikes and complains about Lelaina for being too smart.
- The '90s: SO much.
- Pet Homosexual: Sammy.
- Product Placement: This film has a lot of product placement and product references in the dialogue, including Gap, BMW, Diet Coca-Cola, Pringles, 7-Eleven (its Big Gulp drinks are seen throughout the film), Pizza Hut, Domino's Pizza, Evian, Camel Straight cigarettes, Snickers, McDonald's (Troy mentions a Quarter Pounder with Cheese as one of life's pleasures), Whole Foods Market, Continental Airlines, Cocoa Puffs, Infiniti (Nissan USA luxury automobile division), Ford Motor Company, and Minute Maid. The sheer number of products seen and mentioned in this film is kinda funny considering Lelaina's anti-consumerism speech at the beginning.
- Reality Does Bite: Lelainas little TelePrompTer prank might seem like a hoot, but did she really expect to keep her job after that?
- Really Gets Around: Both Troy and Vickie.
- Rich Suitor, Poor Suitor: Michael (rich suitor) and Troy (poor suitor).
- Romantic Runnerup: Michael's MTVization of Lelaina's documentary does not go over well.
- Take That!: To MTV and The Real World.
- 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