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  • Hilarious in Hindsight: Cliff gets a rock critic review that says he's terrible, but his backing band is pretty good.
    • Cliff also mentions that his generation did not produce its defining song yet. Before the film even reached theatres Nirvana released 'Smells like Teen Spirit'.
  • Retroactive Recognition:
    • Paul Giamatti, in one of his first roles, plays the guy making out with a woman loudly while Steve and Linda are on the restaurant.
    • Jeremy Piven is the cashier who recognizes Steve.
    • Ally Walker is Debbie's roommate Pam.
    • Victor Garber is the guy Debbie ends up with.
  • Sophomore Slump: Cameron Crowe began making this film hot off the success of his first directing effort, Say Anything..., but Singles was released to only moderate success and lukewarm reviews. He'd get his mojo back with the one-two punch of Jerry Maguire and Almost Famous.
  • Unintentional Period Piece: Counting the ways:
    • Grunge and alt-rock is everywhere.
    • Flannel is practically a dress code requirement (although somewhat Truth in Television in Seattle to this day).
    • The dating service that Debbie uses involves VHS tapes instead of any variety of video disc or the Internet.
    • Reference is made to building airplanes, as Boeing used to be by far the largest employer in the Seattle area (Boeing since has left the area; tech companies such as Nintendo, Microsoft, and Amazon are the local heavyweights now).
    • Steve's friend Bailey storing phone numbers on his watch, as opposed to a cell phone.

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