Honorable Mentions:
Jell-O: One of the first pranks ever pulled by Jim on Dwight (on-screen) had Jim putting Dwight’s stapler in Jell-O in the Pilot episode. This caused for a hilarious reaction by Dwight who was trying to show off to the new guy, Ryan, as Michael was showing him around. Michael seems to enjoy the prank too and doesn’t really do anything about it. The best thing to come out of this are the puns that Jim and Ryan come up with, such as “I’m your biggest flan” or “you should have put him in custard-y”. Michael of course tries to come up with one himself to fit in, but utterly fails at it like only Michael Scott can.
Conflict Resolution: This is a bit of a cheat as we never really saw this happen on-screen. But in Season 2’s Conflict Resolution, we see Michael read out a list of Dwight’s complaints against Jim, which are just a whole bunch of hilarious pranks. The best one has Jim putting nickels into Dwight’s phone every day, and as he gets used to its weight, Jim takes out all the nickels and Dwight ends up hitting himself in the head with the phone. I would’ve loved to see this play out on-screen, but just visualizing it makes me crack up, so maybe it’s better that way. Apparently, it’s also John Krasinski’s favorite prank.
Ben Franklin: In Season 3’s Ben Franklin, Jim convinces Dwight that the Ben Franklin ‘stripper’ (who’s actually just an educational impersonator) is indeed the real Ben Franklin. Dwight is 99% sure that it is not, but that 1% of uncertainty leads to asking the impersonator some rapid fire questions that only the real Ben Franklin could answer. The best part of this prank is when the impersonator answers all his questions correctly and instantly, leading Dwight to scream in failure.
Buttlicker: In Season 5’s Customer Survey, Dwight and Jim’s customer feedback is pretty bad (which is a whole other plot line involving Kelly). Dwight is specifically described as being aggressive. Michael takes it upon himself to manage them personally so that they can go back to handling sales calls appropriately. This results in a fake call training between Dwight and Jim where Jim acts as the client under the name “Bill Buttlicker.”
Michael takes this super seriously and Jim uses this opportunity to mess with Dwight and force him to mess up and scream things like “Buttlicker, our prices have never been lower.” The best part of this is how seriously Michael and Dwight take this and it’s like they are on an actual call. There’s real tension on Dwight’s face when Jim offers Michael a purchase a million dollars worth of paper in exchange for firing Dwight. You have to watch the scene to realize its true brilliance.
Future Dwight: Just because Jim transferred to Dunder-Mifflin’s Stanford branch doesn’t mean he’d just stop pranking Dwight. In Season 3’s Branch Closing, Jim reveals how he took Dwight’s stationery and faxes Dwight messages while claiming to be Future Dwight. In this particular instance, he warns Dwight of the coffee being poisoned by someone and to not drink it. Dwight instantly runs to Stanley and knocks over his cup while he’s drinking it. I would’ve loved to see Stanley say something back along the same line of rage as “Did I stutter?”