Jim Halpert (John Krasinski) is one of the most beloved characters to emerge from The Office. There certainly is plenty to like about him: his lustrous hair, amusing facial expressions, his sweet relationship with Pam Beesly (Jenna Fischer), and the very humorous exchanges he had with manager Michael Scott (Steve Carrell) and deskmate Dwight Schrute (Rainn Wilson). Jim's great!
But not always. Upon closer inspection, there are many points throughout the series where Jim behaves in a way that is objectively terrible. He has offered textbook examples on how not to conduct oneself as a co-worker, an employee, a romantic partner, and (arguably) a human being. Simply put, Jim can be just... the worst.
Brutally Dumping Katy
In season two's "Booze Cruise," Michael takes the whole office out on a boat for what is supposed to be a training exercise. But really... it's just a drunken party. During the proceedings, Pam's fiancée Roy (David Denman) officially sets a date for their wedding. Devastated at his true love committing to marry someone else, Jim breaks up with his girlfriend Katy (Amy Adams). The brutal coldness of that break-up is captured in the following quote:
Katy: "Why did you even bring me here tonight?"
Jim: "I don't know. Let's break up."
Jim was clearly in a heartbroken state of Pamlessness, but that's no excuse to crush somebody else's heart. Jim didn't just dismiss Katy as if she didn't matter at all; he also left her stranded on a lake surrounded by people she didn't know. It would be a very safe bet that Jim and Pam did not receive tickets to the premiere of Enchanted.
Letting Michael Fall In The Koi Pond
Jim and Michael head to a sales meeting together in the Season 6 episode "Koi Pond." They make a splash at the meeting, in that Michael falls into a koi pond in the lobby. It's later revealed via security footage that Jim had ample opportunity to stop Michael from falling in, but he didn't.
Koi weren't the only cold-blooded creatures that Michael interacted with that day. At the end of the episode, it's implied that Jim let him fall because he was disappointed that Michael was tagging along with him to the sales call and that he's jealous of Michael's selling skills. But that's even more damning for Jim; it shows that he's willing to let his boss and friend be thoroughly humiliated all because of a bruised ego. Michael also fatally steps on a koi while in the pond, meaning Jim has koi blood on his hands.
Assaulting Dwight Several Times
Jim is famous for his pranks against Dwight. Many of them demonstrate impressive levels of creativity and hard work, but sometimes he skips all that and resorts to physical violence. This includes slapping Dwight in the episode "Traveling Salesman," pushing him over in the episode "Mrs. California," kicking him hard in "After Hours," and throwing a snowball in his face in "Classy Christmas." (Although Dwight does pay Jim back for the snowball, and then some)!
No matter how annoying a co-worker is (and Dwight certainly can be), inflicting physical pain upon them is never OK. It's especially annoying given that most of those occur after Dwight personally saved Jim from being assaulted by an angry Roy in season three's "The Negotiation." Jim has a funny way of expressing gratitude! Realistically, Jim should've been fired for those actions (as Roy was), but he always survived to smirk another day.
Inappropriately Lifting Pam Up
The whole office goes down to the local dojo to see Dwight take on Michael in a fight. Surprisingly, that is not the most awkward thing that transpires there. Jim and Pam start a playfight, culminating in Jim grabbing and lifting Pam into the air. Although she initially laughs it off, Pam quickly becomes uncomfortable and demands that he put her down. She then storms off.
One could argue that Jim was the worst for flirting with an engaged co-worker, to begin with. But to flirt with Pam to the point where it genuinely embarrasses and upsets her takes the awfulness cake. It points to one of Jim's fundamental flaws: he often gets too carried away. Although Jim and Pam's relationship quickly heals (and eventually evolves into marriage), this easily ranks as one of the lowest points in the Jim/Pam saga.
Causing Deangelo's Injury
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Deangelo Vickers (Will Ferrell) was the first person to take the reins of Dunder Mifflin Scranton after Michael's departure. His eccentric behavior and favoritism toward men quickly rub many employees the wrong way, but it wouldn't last long. At Jim's suggestion, Deangelo demonstrates his slam-dunking skills on the basketball hoop in the warehouse. The hoop collapses onto Deangelo's body, knocking him out of commission for good.
It would not have happened if it wasn't for Jim. It was his idea for Deangelo to do the dunk, and Jim egged him on after he expressed reluctance. It obviously wasn't Jim's aim for Deangelo to hurt himself, but there's no doubt he wanted him to be humiliated in front of the whole office. In this case, Jim's sinister motives had disastrous consequences. Thanks to Jim, Office fans would be robbed of the opportunity to see another inspirational juggling routine on the show. A very sad loss.
Hiding And Calling Andy’s Phone
In the Season 3 episode "The Return," Dwight has quit his job, so Andy (Ed Helms) temporarily fills the role of Jim's annoying deskmate. When Andy's singing and "fishing" proves too much to bear, Jim gets his revenge via prank. He steals Andy's phone, throws it into an air vent, and then dials it repeatedly. Andy's inability to find and answer his ringing phone drives him into an intense rage: he proceeds to punch a hole into the office wall.
To steal and potentially damage Andy's personal property and then deliberately drive him over the edge is a new low, even for Jim. Predictably, Jim was not caught or punished while Andy was shipped off to anger management. Although this was Jim at his worst, for Andy — it worked out for the best. While in anger management, Andy ironed out many of his character flaws. He returned a more likable person and was eventually promoted to Regional Manager, above Jim!
Taking The Job In Philadelphia
There was definitely trouble in paradise for Jim and Pam in the show's ninth and final season. All that trouble starts in the season opener ("New Guys") when Jim accepts a job at a Philadelphia-based sports company without consulting her. Very impish.
To be fair, it's evident that Jim agonized over the decision and did a lot of thinking before taking the job. But he still took it. In doing so, he willingly inflicted strife upon his wife, kids, and the workplace he's been at for over a decade. Jim spends much of the season living it up in a different city, while Pam is left to handle their two kids and the adult children she works with at Dunder Mifflin.
Distributing Michael's Screenplay
In Season 2's "The Client," Pam stumbles upon something interesting in Michael's desk while he's away at a meeting. It's a screenplay for an action film entitled Threat Level Midnight that Michael wrote. Sensing laughs, she shows it to Jim, who then makes numerous copies and leads the entire office through a table-read of Michael's screenplay.
Pam initially crossed the line by reading Michael's script and giving it to Jim. But Jim went way beyond the line when he shared it with the rest of the office and hosted a group mocking session. Ask any aspiring writer, and they'll tell you that one of the most mortifying things imaginable would be to have their precious creation be ridiculed by everyone they know. Thankfully, it appears that Michael never found out about those shenanigans. His movie eventually got produced, and it currently sits on over 10 million YouTube views! Mission accomplished, Michael Scarn.
Ripping Dwight's Suit Off
Shown via flashback in the episode "Free Family Portrait Studio," Jim secretly replaces Dwight's suit with one made with tear-away Velcro. When Dwight walks into work, Jim rips the suit from his body, leaving him in his underwear for everyone to see... and laugh at.
Jim acknowledges that he “may have gone too far” with this one, and it's hard to argue. Not only is this prank needlessly humiliating, but it's also a worrying illustration of how much effort Jim is willing to expend to make his co-worker suffer. For those of you at home, ripping the clothes off a co-worker's body in public and without consent is a bad thing to do. Don't be a Jim.
Forcing Ryan Into A Tiny Office
Jim reigned as co-manager of the Scranton branch for much of Season 6. One of the biggest contributions was in the episode "Shareholder Meeting," where he relocates the lazy Ryan (B. J. Novak) into a new office - a cramped closet!
Many fans defend (and even celebrate) Jim's decision here, given that Ryan is quite the arrogant jerk. But when you think about it, it's a gross act of hypocrisy on Jim's part. He sentences Ryan to solitary confinement because Ryan goofed off for one day. Jim himself goofed off and tormented others for many years, and not only did he keep his desk, but he also got a sweet promotion!