2- “Overnight Delivery” #52PickUp 2017

This week’s film will feel familiar and make you wonder if cryptomnesia happens more than you think:


Overnight Delivery is a 1998 film about a college man, Wyatt Trips (Paul Rudd) finds out his long-distance girlfriend (Christine Taylor) has cheated on him, so he gets drunk, takes a naked photo with a stripper, Ivy Miller (Reese Witherspoon), and mails her a nasty letter via overnight delivery. But then he finds out that she wasn’t cheating on him, and now must travel across four states to retrieve the envelope before it reaches her doorstep.



Original Cinema Quad Poster - Movie Film Posters

Road Trip came out in the year 2000, two years later.


The plot is nearly identical, except the two cities are different, and that Breckin Meyer and Amy Smart’s characters actually have sex. It’s alarming how such a precise conceit can be “made new” with a little raunchy flair. And this is coming from a guy who loved Road Trip when it came out.


I actually had watched Overnight Delivery way after Road Trip, and I thought it was the other way around, until I used my trusty old IMDb for reference. I was had.

Alright, let’s get back to the movie of the week here. Overnight was surprisingly a smartly-written film. The dialogue is almost too highfalutin at times, and seems out of place in a small rom com like this. Let me give you a funny example.

When a plan to retrieve the envelope fails, Trips freaks out on poor Ivy (his ride) and says “Helping me out?! Lady, if my wheelchair was getting kicked off the side of the Achille Lauro…” reminded me of this:

Well the Achille Lauro is something that I had to look up. The MS Achille Lauro is an Italian ship that was hijacked by the Palestine Liberation Front in 1985. So are we to believe that the reference was over thirteen years old? Or was it a general statement? Either way, why would anyone reference that ship in a Rom Com?

But funnily enough, the rest of the film is chock full of contrived plot devices that are so unlikely, that it’s obvious.

Trips gets dropped off at the airport by Ivy and is boarding the plane to fly nonstop from Minnesota to Memphis to stop the delivery, but while on the plane, he sits next to the briefly mentioned serial killer (Killer Beez, J.D. Beesley) played by– What do ya know?! TOBIN BELL. IF you don’t know who he is, then does this ring a Tobin Bell?


Yes, the killer in Saw predated that film by six years, playing an unlikely murderer.

He holds Trips hostage, and gets gunned down (off-camera), but Trips gets away, climbs a nearby fence and hey wouldn’t you know it? Lands right in front of Ivy. Too convenient if you ask me. Yes, that was a long set up to the point I was trying to make, thank you for noticing.

The Express driver of the initial delivery to the airport (on his first job ever, played by the late Larry Drake), must now drive the mail all the way to Memphis. He becomes obsessed with this task, even going as far to refuse Reese’s offer of her own body to him.

To which he says: No Thanks. Hmm… I’m disappointed in you, Larry.

They continue to by chance run into this guy, even if Trips and Ivy are running into trouble along the way, and the driver is unrelenting in his quest to deliver this one envelope.

In the end, it turns out Trips’ girlfriend is indeed cheating on him, but Trips already dumped her, leaving him free to get with Ivy. End of story.

“Cactus Thighs?! I’m NOT FAAAAT!!!!!”

What’s the franchise like?

Well it was followed by an adaptation and a direct-to-video sequel:

Where/ when did I first see it?

I first rented this around 2001 at my local Video Market.

How does it hold up?

Aside from its cheesy moments, the movie is actually pretty funny at times, and as mentioned before, well-written. It has its convenient plot contrivances, but hey, most films do to some extent.

Plus, it’s always great to play the “Where Are They Now?” game and pick out the now-famous celebs.

A few things to Note:

Speaking of! Sarah Silverman was one of the people who initially began the hunt for the envelope! She was an employee at the Global Express office, and could have stopped the Trips before it even began! See what I did there?

Unable to find a photo of her in the film.

The Joker:

I mean, it has to be, Paul Rudd, right? He was hamming it up the entire time! But, it’s almost accidentally Larry Drake because his ADR and facial expressions were absolutely hilarious. So TIE!

Lessons Learned?

  1. Never ship something you’re unsure of via Overnight Delivery.
  2. Always assume she’s cheating… if you’re a psycho.
  3. Since when did it become Valentine’s Day?!


Where can you see it?

Check out Overnight Delivery on CanIStream.It?

-Jamie (@GuyOnAWire)


One thought on “2- “Overnight Delivery” #52PickUp 2017

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