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Film / Overnight Delivery

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Overnight Delivery is a 1998 Direct to Video romantic comedy. The main arc of the film is a highly formulaic Road Trip Romance, made watchable mainly by a pair of highly likeable leads, both of whom are probably more recognizable now than when the movie was made.

Wyatt Tripps (Paul Rudd) is a smart and driven college student who spends most of his time pining over his girlfriend, who goes to a different school a thousand miles away. One night, he becomes convinced his girlfriend is cheating on him, gets drunk, and has a chance encounter with Ivy Miller (Reese Witherspoon), an impressively canny stripper who convinces him to write a particularly nasty breakup letter and send it by an overnight delivery service.

The next day, Tripps realizes his mistake, and enlists Ivy's help to get the package back before it gets to his girlfriend. A series of misadventures later and they find themselves on a road trip across the country, and wondering if he's racing toward the right girl.

Tropes Associated With This Film Include:

  • Absurdly Dedicated Worker: The Global Express deliveryman. You would expect a man who sees his truck on fire to at least bother to try to put it out before continuing his route.
  • Artistic License – Geography: The actual University of Memphis tower dorms were a lot less glamorous at the time, but the film needed a different physical setup for some of the final shenanigans. Everything in the movie was filmed in Minnesota instead.
  • Berserk Button: She may play by her own rules when it comes to relationships, but NOBODY calls Ivy a slut.
  • Betty and Veronica: Kind of inverted. The sweet, blonde, virginal Kim turns out to be lying and manipulative, while the streetwise, brunette stripper Ivy turns out to be both nicer and more sensitive than she appears.
  • Disposable Fiancée: Not quite a fiancee, but Tripps does plan on marrying his girlfriend before Ivy comes along. In the end, she turns out to have been cheating on him after all. Though he finds out after he dumps her.
  • Dumb Blonde: While not especially dumb, Kim is a pretty blonde, former cheerleader who's presented as being notably dimmer than the two leads.
  • Good Bad Girl: Ivy works as a stripper and is evidently sleeping with one of her professors. Despite that, she's shown to be kind, highly intelligent and entirely moral.
  • Irrevocable Message: The break-up letter is the driving force of the plot.
  • Nerds Are Sexy: Not nerds, exactly, but both Wyatt and Ivy are shown to be pretty smart and well-read. Wyatt's girlfriend, by contrast, is implied to be a little dumber.
  • Last Girl Wins: Tripps starts out willing to do anything to marry his high school sweetheart. By film's end, things have changed.
  • Obstructive Bureaucrat: The clerk for the delivery company turns out to be someone Tripps had accidentally offended the previous day. She makes quite sure that he won't be able to get the package back through the proper channels.
  • Poor Communication Kills: Tripps starts worrying about his girlfriend cheating on him, and when he tries to call her, her roommate tells him she's "out with The Ricker" and stars ranting about how much noise The Ricker was making last night. Tripps naturally takes this as confirmation of his fears. Turns out that The Ricker is a dog she's taking care of. Then, at the end, that turns out to be a lie, and she actually is cheating on him.
  • Product Delivery Ordeal: Inverted. The protagonist, Wyatt Tripps, is convinced his girlfriend is cheating on him, so he writes a particularly nasty breakup letter and sends it by an overnight delivery service. However, come the following morning, he realizes he made a mistake and now has to prevent the delivery of the letter or get it back before it reaches his girlfriend. The antagonist is the Unstoppable Mailman who is committed to delivering the letter.
  • A Simple Plan: Once Tripps realizes he can't get the letter back, he decides to go to Memphis to intercept it. Sounds easy enough...
  • Unstoppable Mailman: The Global Express driver is very commited to his job. He's absolutely determined to make sure the package gets to it's destination on time:
    Driver: (while driving away in a flaming truck) As God is my witness, you will not stop this package! Not on my watch!!
    Ivy: That is one dedicated professional.