Jim Halpert's Best Pranks From The Office, Ranked

By Jake Schroeder
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Selling paper isn't for everyone. In the humdrum world of slinging stationary and closing on cardstock, it sometimes becomes necessary to manufacture your own entertainment. For Jim Halpert, nothing was better for getting through the day at Dunder Mifflin than finding the most unexpected ways to prank overzealous and obnoxious co-worker Dwight K. Schrute.

Eventually, the two became unlikely friends — but only after Jim unleashed a treasure trove of unforgettable pranks. Here are some of the best.

30. When Jim Created a Macro That Automatically Changed Dwight's Name to "Diapers"

Jim's earliest pranks on Dwight varied from impromptu, juvenile efforts to sophisticated, carefully-planned gambits. While the latter earned plenty of screen time, it was often the subtler, more childish hijinks that stand out, even if we never saw them play out on screen.

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In season two's "Conflict Resolution," as Michael read a litany of charges Dwight has directed toward Jim, he revealed a time when Jim programmed Dwight's word processor to auto-replace his name with "Diapers." The genius of this practical joke is its simplicity. For little effort, Jim lands an easy jab on Diaper's ego. Excuse me, Dwight's ego.

29. When Jim Turned the Interrogation Back on Dwight

When Dwight found half a joint of marijuana in the Dunder Mifflin parking lot, Jim sensed danger—and opportunity. "Dwight finding drugs," Jim pointed out, "is more dangerous than most people using drugs." As Dwight (dressed in full police costume) began interrogating his co-workers, Jim seized the moment.

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Jim suggested that perhaps Dwight is the person who brought the drugs to work and merely forgot, due to the memory-loss effects of smoking marijuana. "That's not how it works," Dwight asserted, not realizing the corner he'd painted himself into. "Now how do you know how it works?" Jim asked. Checkmate, Schrute.

28. When Jim Got Dwight to Scale a Phone Pole

The key to any successful prank is to know the weaknesses of the prank's target. Jim understood that Dwight's paranoia and curiosity were absolutely insatiable. He would follow any small suspicion as far as he needed until he found the answer to the question bothering him.

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With $20, Jim purchased 500 feet of red wire and ran it from the back of Dwight's computer to the top of a telephone pole in the office parking lot. Dwight, of course, scaled the pole, and of course, Jim had to climb up there first, proving he'd go to any height (pun intended) to mess with Dwight.


27. When Jim Beat Dwight at Poker by Coughing

"Casino Night" proved to be memorable for many reasons, so you might've forgotten how Jim wiped the floor with Dwight in poker. Not every prank is planned or even fully understood. Sometimes, Jim simply stumbled into the chance to take advantage of Dwight's delusions.

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Dwight arrived at Casino Night expecting to leave with his pockets full, thanks to his "acute ability to read people." That included Jim's "huge tell" of coughing every time he had a good hand. Jim quickly realized this tell and coughed his way to victory. If only he could have read Pam like he did Dwight.

26. When Jim Stared at Dwight's Forehead

Absence has a way of making the heart grow fonder. It also has a way of making people fall back into old habits quickly. When Jim returned to the Scranton branch of Dunder Mifflin after time away in Stamford, Dwight was confident he’d maintain the upper hand. "Fact," he greeted Jim, "I am older. I am wiser. Do not mess with me."

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Jim didn’t miss a beat, returning Dwight's greeting by staring a few inches over his gaze. Before long, Dwight was standing on his tiptoes, rage in his eyes, as he demanded Jim "stop acting like an idiot."

25. When Jim Made Dwight Sell Paper to Bill Buttlicker

When Jim and Dwight received subpar customer satisfaction reports from Dunder Mifflin's surveys, Michael sat them down to oversee them with a more "microform of management" (what's that called again?). Seated at the conference table, Michael had Dwight do a mock sales call with Jim to make sure he wasn’t being too aggressive with clients.

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Jim answered the phone as the hard-of-hearing Bill Buttlicker and was offended when Dwight questioned his name and yelled at him. Dwight gave the phone to his boss, and Buttlicker agreed to buy $1 million worth of paper products — but only if Michael fired Dwight.


24. When Jim Formed a Fake Alliance with Dwight

Dwight's fear of downsizing in the first season of the show forced him to do the unthinkable: he approached Jim to form a Survivor-inspired alliance in order for them to "help each other out."

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The alliance blows up in both of their faces. Jim immediately tells Pam about the secret pact, and Dwight ends the day in a box inside the warehouse. Jim, meanwhile, gets a little too affectionate with Pam, grabbing her hand in front of her fiance, Roy. He confronts Jim, who looks to Dwight for support on the alliance prank. Dwight plays dumb, leaving Jim high and dry.

23. When Jim Made Dwight Hit Himself in the Head with His Phone

This is yet another prank we never see on camera, but it's also one you can't get out of your head once you imagine it. Back in season 2's "Conflict Resolution," as Michael reads off what sounds like a greatest hits of Jim's pranks, we learn of the day Dwight hit himself in the head with his work phone thanks to Jim's long-term planning.

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For weeks, Jim added one nickel at a time to Dwight's headset until he got used to the weight. When he emptied the nickels, muscle memory took over. A simple prank, and a cost-effective one, too.

22. When Jim Convinced Dwight It Was Friday … on Thursday

Jim was notorious for his ability to plan out pranks, but perhaps his greatest talent was the ability to do it on the fly. There's no better example of this than the Thursday Dwight showed up to work convinced it was Friday.

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For the rest of the day, Jim reinforced Dwight's confusion with subtle clues. He called a friend about getting together on the 15th, which, Dwight noted, is a Saturday. He even enlisted Pam, who mentioned the previous night's episode of The Apprentice that Dwight missed for laser tag and drinks. On Friday, the punctual Dwight almost missed the entire workday as a result.


21. When Jim Used Bed Bugs to Get Out of a Thirst Trap

In one episode, Cathy dropped in on Jim's hotel room wearing very little and made herself a little too comfortable for Jim's liking. How else could Jim get out of that awkward situation but by calling on Dwight for a bailout caper?

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When Jim told Dwight he saw a bed bug, Dwight burst in, checked Jim's greasy hair, ripped off the sheets and his clothes and used his body heat to attract the fictitious bugs. "Then we'll see who's laughing!" Dwight crowed. Cathy wasn't, but Jim offered a smile — until Cathy moved into his shower.

20. When Jim May Have Gone Too Far

Even Jim had to admit he might have gone too far in "Free Family Portrait Studio" at the end of season 8. When he found out where Dwight got his dry cleaning done, he custom-ordered a suit that matched Dwight's stitch for stitch — with one exception. He created a tear-away velcro version and stripped Dwight to his underwear in the parking lot.

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The joke got a rare laugh from Stanley, but the consequences took a toll on Jim's family. Dwight used a free family portrait studio at work to get Jim's kids into the office and seek vengeance.

19. When Pam Helped Jim Convince Dwight the CIA Was Recruiting Him

There's no icebreaker quite like tricking Dwight into thinking he's being recruited a secret agent. When Jim returned to Scranton with a new girlfriend, things were understandably icy between him and Pam. So, Pam used Christmas as the chance to help re-establish their friendship.

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For months, Pam sent Dwight letters from the CIA, and on Christmas, she handed him a folder marked "classified." Jim hesitated, but eventually he convinced Dwight a helicopter would pick him up from the office roof. The escapade ended when the CIA aborted the compromised mission and Dwight chucked his cell phone into the night air.


18. When Jim Intercepted All of Dwight's Calls

For someone as well-versed in science fiction as Dwight, he's awfully slow when it comes to technology. This is a weakness Jim was happy to exploit when Dwight left his cell phone sitting out on his desk. Jim paired the device to his bluetooth headset, and madness ensued.

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First, Jim took a work call of Dwight's phone, infuriating him to no end. Then Pam called Dwight, and Jim answered. Pam said he sounded sexy, and Dwight routed his cell phone to his work phone. Too late — Jim already forwarded the work phone to his own. It always pays to think ahead.

17. When Jim Put Dwight's Stuff Inside the Vending Machine

It pays to have friends with powerful jobs. For Jim, a friendship with Steve, the vending machine guy, turned into the perfect opportunity to mess with Dwight. One by one, Jim placed all of Dwight's personal items inside of the vending machine in the office's break room.

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When Pam bought Dwight's pencil cup for a dollar, Dwight reached for his wallet to buy back his things, but he found it, too, was in the machine. Luckily, Jim was there to lend a helping hand—in the form of a bag of nickels. Another sound and efficient investment by Mr. Halpert.

16. When Jim Put a Plastic Knife in Naked Dwight's Hand

With Michael out of town, Jim took advantage of Dwight's authoritarian inclinations to turn a meeting into a roasting of Dwight, who was recording a conference room meeting for Michael to listen to.

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The audio format provided the perfect platform for Jim's antics. "Oh my God, Dwight, what are you doing?" Jim interrupted. "You're not allowed to take off your pants in the middle of the office." Soon, Jim painted a verbal, recorded picture of Dwight nude and wielding a plastic knife at Stanley's neck. Unfortunately, Andy took the charade too far by supposedly chopping off Phyllis' head with a chainsaw.


15. When Jim Gave Dwight an Unforgettable Christmas Present

'Tis the season to be jolly. 'Tis also the season to give Dwight a Christmas present he'll never forget. Dwight's desk was a favorite area of target practice for Jim — more on that to come — and with the holidays approaching, he decided to cover Dwight's workstation entirely in wrapping paper.

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Dwight was unimpressed and mocked Jim for wasting time. He was also unimpressed by Jim's black belt in gift wrapping and promises to unwrap everything in five minutes. It took far less time than that—Dwight fell to the floor when he sat on his chair and desk, which were really just empty, paper outlines.

14. When Jim Turned Mega Desk into Quad Desk

Jim's return to work from paternity leave got off to a bad start when he found Dwight had commandeered his desk to form a "mega desk." The station was complete with command central, surveillance and business areas. Not one to be outdone, Jim fired back with a desk-related maneuver of his own.

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Enter "Quad Desk," a stand-up, triangularly-stacked workstation whose name offended Dwight. "That's ridiculous," Dwight said. "This is made up of three desks." As Jim realized the desk needed a new name, Dwight's phone rang, and he crawled into the tiny space beneath Quad Desk to answer the call.

13. When Jim Put Dwight's Desk in the Bathroom

Kudos to Jim for the sheer logistical expertise required to move Dwight's entire desk into the men's bathroom. When Dwight arrived at work and found his desk missing, he accused Jim of being "unprofessional." "Well," Jim replied, "you're the one who lost his desk."

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Just as Dwight went to tell Michael, Jim began a game of Hot and Cold. Following Jim's cues, Dwight found his desk in the bathroom. The good news? His phone still worked, and he helped Jim find a discount he'd been looking for. The bad news? It turned out Kevin doesn't wash his hands before leaving the men's room.


12. When Jim Framed Dwight for His Own Murder

The clues were there all along. Remember "Conflict Resolution," when Dwight tattled on Jim for putting a bloody glove in his desk and accusing him of murder? In Season Eight's "Tallahassee," Jim took it to the next level.

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While Dwight woke his fellow employees in a Tallahassee hotel, Jim, up at 4:15 a.m. like any father of young kids, staged a murder scene in his hotel room. There was blood on the sheet, cash in a suitcase and a red warning on the wall that read, "Dwight did it." When Jim's limp body fell out of the closet, Dwight and Erin screamed bloody murder.

11. When Jim Cracked the Case of the Michael Scott Paper Company

Some practical jokes are strictly for laughs. Others help save your wife's failing company and help her get a new job. When Dwight discovered the Michael Scott Paper Company was going broke, he rushed to Vice President Charles Milner, who was negotiating a buyout with Michael and Co.

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Jim alertly stopped Dwight in his tracks by questioning his track record of cracking cases. Charles, unimpressed by Dwight's detective work in "The Case of the Beet Bandit," called him and Jim "morons," ignoring Dwight's warning. The buyout went through, and Pam ended up back at Dunder Mifflin with a better job.

10. When Jim Convinced Dwight He Was on the Radio

When local radio host Iris Black called Sabre seeking a guest for her show, "Biz Wiz," Dwight jumped at the chance to promote his work and build his brand. Unfortunately for Dwight, Iris called back later to cancel the interview. Even more unfortunately for Dwight, nobody told him.

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Instead, Jim produced a fake radio show hosted by Nellie and soundtracked by Darryl, and the mock-interview went terribly for Dwight. First, they convinced him to take off all his clothes. Then, they convinced him he was tanking the company's stock during a toxic paper crisis. It was gotcha journalism, and Dwight got gotched.


9. When Jim Kept Track of Every Second Dwight Wasted

There are traps we set for others, and there are traps we set for ourselves. Dwight cornered himself in one episode when he said in a business ethics lecture that he never wasted time at work.

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Enter Jim with a stopwatch and too much time on his hands. It started with a four-second yawn and a 17-second personal conversation. Jim then baited Dwight with Battlestar Galactica blasphemy, but Dwight was determined. Before the day was over, Dwight peed in a soda bottle while filling out expense reports. Still, he managed to find 20 minutes for "personal time" with Angela.

8. When Jim Convinced Dwight He Was a Vampire

Dwight's discovery of a bat inside the office of Dunder Mifflin set off an unforgettable chain of events. Meredith got bit and, we later discover, likely contracted rabies. Jim didn't get bit, but that doesn't mean he didn't smell blood in the air.

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By inspecting his teeth, feigning fear at "ice cold" garlic bread and displaying sensitivity to light, Jim insinuated he’d turning into a vampire. It made sense to Dwight — according to him, a vampire would live in a "-sylvania" state. Bonus points to Jim for the risk incurred—he was lucky Dwight never stabbed him in the heart with a stake.

7. When Jim Sold Dwight a Sack of Magic Beans

Inspiration for tomfoolery was everywhere for Jim, and perhaps his role as the father of young kids planted the seed for this particular endeavor. In season 7's "Garage Sale," Jim "accidentally" left out a bag marked "Professor Copperfield's Miracle Legumes." He then regaled Dwight with a tale of a Jamaican mystic who sold him the legumes and vanished.

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Through reverse psychology, Jim convinced Dwight of the legumes' magical powers, and Dwight ended up trading a $150 telescope for the beans. You can always buy another telescope, after all. Miracle Legumes don't exactly grow on trees.


6. When Jim Was Really Asian All Along

Only Jim could turn a trip to the dentist into an opportunity to force Dwight into questioning the fundamental nature of reality. With help from Pam and their actor friend Steve, the Halperts threw Dwight into a state of existential confusion when Steve, an Asian man, pretended to be Jim.

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As "Jim" passed every test Dwight threw his way — questioning his sales history, nailing his voicemail password — Pam delivers the prank's kiss of death, laying a smooch right on Asian Jim's lips. When Dwight discovered a photo of Pam, Asian Jim, and their mixed-race babies, it was a knockout punch.

5. When Jim Sent Dwight Faxes From Future Dwight

Dwight's susceptibility to science fiction was a vulnerability Jim preyed on time and time again. When he left Scranton for Stamford, Jim looked to the future … literally. Before he left, he snagged a box of Dwight's stationery. From Stamford, Jim sent Dwight faxes — from himself, in the future.

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The audience only saw this prank play out in one instance. Future Dwight warned Past Dwight that the coffee was poisoned, which lead Past Dwight to slap a full, hot mug from Stanley's hands. "You'll thank me later," he insisted. No matter the time or place, Jim always had something up his sleeve.

4. When Jim Trained Dwight with Altoids and Classical Conditioning

Jim had a reputation as a classic underachiever, so it's a little surprising to see how closely he paid attention in high school science. In this prank, Mad Scientist Jim borrowed from Pavlov's playbook and trained Dwight like a dog.

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In his experiment, Jim replaced the sound of a bell with the sound of a computer booting up, and he replaced the dog's food with an Altoid mint. Every time he restarted his computer, he gave Dwight a mint — until the day he didn't, leaving Dwight's extended arm empty-handed and his mouth tasting "so bad all of a sudden."


3. When Jim Stole Dwight's Identity

Imitation is the most sincere form of flattery. It's also an easy way to drive Dwight crazy. When Jim saw a $4 pair of glasses in a drug store, he decided to create an entire Schrute ensemble, complete with calculator watch, short-sleeve mustard-colored button-down and middle-parted hair (an $11 investment, in total).

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The payoff was well worth it. Jim peppered Dwight with questions about bears, beats and Battlestar Galactica before Dwight realized what was going on. When Jim placed a bobblehead on his desk, it was the final straw for Dwight. "Identity theft is not a joke, Jim," he angrily shouted. "Michael!"

2. When Jim Put Dwight's Stuff in Jello

Classics have a way of transcending time, sticking (pun intended) in memories long after they debut. They aren't necessarily flashy, but they endure because they connect with people in a unique and transcendent way.

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There is no more quintessential Jim prank on Dwight than when he put Dwight's stapler in Jello. This prank took place in the pilot as our introduction to Jim's shenanigans and Dwight's easily-acquired frustration. "He put my stuff in Jello again!" Dwight shouted, revealing that Jim had played this number before (for the third time, in fact). And that's just fine — the classics are worth repeating.

1. When Jim Bailed on Being Dwight's Bestest Mensch

The winding road of Jim and Dwight's friendship lead to Dwight naming Jim the "bestest mensch" at his and Angela's wedding. Unfortunately, Jim discovered, he could not be Dwight's bestest mensch because Dwight was older than him, which goes against tradition. Dwight hadn’t heard of this tradition, but Jim insisted. "I just really wish there was something I could do," Jim said, before throwing his trademark glance toward the camera.

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In walked Michael. "I can't believe you came," Dwight exclaimed. "That's what she said," Michael replied. The audience, as usual, was left smiling and satisfied as Michael became the even bestest-er mensch.