The Office’s Jim Halpert is by all means one of the wittiest characters to ever appear on television. His patent blend of sarcasm and well-timed jibes gave the show a lot of its sleek humor. But Jim was also quite self-aware about his behavior and coping mechanisms, which was very refreshing.
His character arc also got a very sound development as he became more reliable and learnt to become accountable. Jim could be the funniest guy in the room, but would also occasionally give way to his real emotions. Here are some his funniest and some of his most profoundly heart-breaking quotes ever said by Jim.
10 Funniest: "I Am About To Do Something Very Bold At This Job That I've Never Done Before. Try."
Every The Office fan can vouch for Jim’s lack of effort; the fact that he had excellent sales numbers was pure luck and Jim had been pretty cheeky about how much he slacks off. But in Season 4, episode 17 Jim tries to land his biggest client ever and finally admits that for the first time in his career he actually wants to make an effort to GET the account. And after much persuasion over a game of golf, he finally signs the client.
9 Heartbreaking: "I Kinda Put It All On The Line. Twice, Actually. And She Said No."
This is one of the few moments on the show where Jim had actually opened up about how he really felt about Pam’s rejection. After Jim is transferred to Stamford, he is reunited with Michael and Dwight for a convention in Philadelphia. Michael confronts Jim and asks him if he left Scranton because he didn’t like his management. It was then that Jim opens up and tells him how hurt he was after being rejected by Pam twice and decided to leave for good.
8 Funniest: "You're Looking At The Master Of Leaving Parties Early."
Jim Halpert had some of the best hacks to navigate social awkwardness and fans just never game him enough credit. In Season 8, episode 4, Andy throws a garden party where he invites his co-workers. Jim leaves the party early and reveals he has a very well-planned system which he falls back on when he needs to leave a party early.
“The key is you have to make a strong impression, so you want to have a picture taken, you want to say some peculiar non sequitur that people remember… I don’t want to brag but New Year’s Eve? I was home by nine,” he reveals.
7 Heartbreaking: "Everything I Have I Owe To This Job...This Stupid, Wonderful, Boring, Amazing Job."
This line marks an interesting progression in Jim’s character arc, mainly because he hasn’t always loved being a part of Dunder Mifflin, and never really liked his job. But by the finale, Jim had married, had kids, made some steady friends, all thanks to this company. And Jim addresses all this as he talks to the camera crew in the finale. So his moment of epiphany was a major defining moment for the show as well as it tied together how crucial the company was for each of them, but especially for Jim and Pam.
6 Funniest: "Dwight Tried To Kiss Me."
This underrated sequence often gets overlooked by fans when they’re recapping the show’s most hilarious moments. During the conflict resolution episode in Season 2, Jim pranks Dwight by making an absurd claim that Dwight had kissed him; the funniest part is everyone at the meeting understood Jim was joking, except Dwight. “Dwight tried to kiss me, and I didn't tell anyone because I'm not really sure how I feel about it. And I’m not making a formal complaint but I really think we should talk about it,’ Jim quipped.
5 Heartbreaking: "It’s Something I Wouldn't Wish On My Worst Enemy. And That Includes You."
Dwight’s heartbreak was something that made The Office fandom really sad because as annoying and infuriating as Dwight is, he was unbearably sad over his break-up with Angela. In fact, one of the biggest bonding moments between him and Jim happened when Jim tried to console him as he cried on the stairs.
Jim opened up about how he felt as he dealt with his own heartbreak when Pam was about to get married. “I couldn't sleep. I couldn't concentrate on anything. And weird stuff, like food had no taste. So my solution was to move away. It was awful. And it is something that I wouldn't wish on my worst enemy. And that includes you,” Jim said.
4 Funniest: "I Miss Dwight. Congratulations Universe, You Win."
Despite their differences and constant bickering Jim and Dwight do share a very complex and special relationship, and sadly they only realize it when they are away from each other. In Season 3, Michael fires Dwight because he suspects that he went behind his back once again. But Dunder Mifflin never gets any peace because Andy is a bigger menace than Dwight ever was. Not only does he get on Jim and Michael’s nerves but he also tries the patience of the entire office. It is then that Jim realizes that he may actually be missing Dwight.
3 Heartbreaking: "And Then Tomorrow, I Can Tell You...What A Great Boss You Turned Out To Be. The Best Boss I Ever Had."
Fans have noted that though Jim had ridiculed Michael during the first three seasons, and had often made jokes at his expense, he started appreciating him more as he himself rose in ranks. When Jim was promoted to be co-manager, he shared a lot of Michael’s burdens and came to understand how difficult Michael’s job really was. Even though they were always on friendly terms, now there existed mutual respect between the two. And when Michael left Dunder Mifflin, Jim opened up about how much Michael’s leadership meant to him.
2 Funniest: "One Day, Michael Came In Complaining About A Speed Bump On The Highway. I Wonder Who He Ran Over Then."
When Michael runs over Meredith with his car, the entire office is left flabbergasted. The weirdest thing was that this happened right outside the office building, and Michael wasn’t even speeding, he was just distracted as he was talking to the camera crew. While everyone at Dunder Mifflin coped with Meredith’s accident in their own way, Jim obviously resorted to humor. This line was executed particularly well, as Jim was shown telling it to the documentary crew right before Michael was shown actually defending his actions.
1 Heartbreaking: "Plan A Was Marrying Her A Long Time Ago. Pretty Much The Day I Met Her."
Jim and Pam’s love story is so flawless, it deserved its own Disney movie. It has been very obvious to fans of the show from the very start that the two co-workers will wind up with each other. And Jim has always been in love with her, although there have been some challenges in her relationship. It was right before their boat wedding that Jim reveals that he has actually been in love with Pam from Day 1. “The boat was actually Plan C. The church was Plan B. And Plan A was marrying her a long, long time ago. Pretty much the day I met her,” he revealed.
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