23 Funny And Cringey Moments From "The Office"Skip To ContentHomepageSign InSearch BuzzFeedSearch BuzzFeedlol Badge Feedwin Badge Feedtrending Badge FeedCalifornia residents can opt out of "sales" of personal data.Do Not Sell My Personal Information 2022 BuzzFeed, Inc PressRSSPrivacyConsent PreferencesUser TermsAd ChoicesHelpContactSitemapPosted on 27 Apr 2022 Here Are 12 Moments From The Office That Had Me In Stitches And 11 That Had Me Cringing My Socks Off I genuinely can't watch Phyllis and Bob's wedding episode. by Benjamin DzialdowskiBuzzFeed StaffFacebookPinterestTwitterMailLink The Office – the defining mockumentary comedy to many – trod a fine line between cringey and hilarious and would constantly swing between the two Tap to play GIF Tap to play GIF NBC Let s take a look at the moments that I think were truly hilarious and the times when I personally couldn t stand to watch it 1 Starting with hilarious we have to begin with Dwight s identity theft NBC Jim's pranks on Dwight were a constant delight. This particular one has to take the biscuit, largely due to Dwight's reaction – "Identity theft is no joke, Jim!" View this video on YouTube youtube.com 2 From bears to unbearable Jim s accidental pregnancy reveal at their rehearsal dinner was hard to watch NBC Oh, Jim. While Michael's rambling speech may have been Jim's motivation for stepping in to give a toast, he did NOT make it any better whatsoever! View this video on YouTube youtube.com 3 On a funnier but still very mean note Michael s reaction to Toby s return from Costa Rica was utterly hilarious NBC Poor old Toby was always on the receiving end of Michael's cruelty. That being said, Michael's reaction here is absolute gold! View this video on YouTube youtube.com 4 Speaking of Toby perhaps his cringiest moment was touching Pam s leg – it s SO bad NBC This moment was truly horrible to watch. Toby saying, "I'm going to Costa Rica" before vaulting the fence is brilliant, but the moment everyone stares at him after he touches Pam's leg is unbelievably awkward. View this video on YouTube youtube.com 5 Something that was pure joy to watch was the lip dub opening NBC Every part of this was so joyous, particularly Michael's frantic magic and Dwight's very on-brand knife wielding at the end. View this video on YouTube youtube.com 6 One of THE most hilariously awkward episodes is The Dinner Party which kind of dips into both categories NBC This one totally depends on your threshold for cringe – some may say it's brilliant and others can't stand it! From Jan playing "That One Night" and holding Jim's hand, to Dwight bringing his old babysitter, this episode had countless iconic moments. View this video on YouTube youtube.com 7 I think we can all agree that Dwight s fire drill episode is one of the funniest ever – notably Angela s cat chuck moment NBC This episode is so quintessentially Dwight. View this video on YouTube youtube.com 8 But back to more awkwardness we have to mention the great fish tank destruction of season nine NBC Darryl Philbin – a relatively reliable office member, right? Particularly compared to the others! However, his jump shot fish massacre in his big interview with Jim’s colleagues was straight out of the Michael Scott handbook. View this video on YouTube youtube.com 9 Back to funny we can t forget Dwight s Billy Joel cover when he discovered that Ryan had ~indeed~ started the fire NBC "I guess they don’t teach you how to operate a toaster oven in business school." View this video on YouTube youtube.com 10 But surely the episode that wins most cringey ever has to be Scott s Tots NBC Everything about this – EVERYTHING – is so unbearable. "I've made some empty promises in my life, but hands down that was the most generous". Then, when he gives them the batteries, it's all just too much. Watch at your peril View this video on YouTube youtube.com 11 Just as iconic but far easier to watch is Kevin s famous chilli NBC "The trick is to undercook the onions." View this video on YouTube youtube.com 12 Onto another almost unwatchable moment Date Mike NBC "Hey, I'm Date Mike, nice to meet me. How do you like your eggs in the morning?" I deffo got second-hand embarrassment from this one. View this video on YouTube youtube.com 13 I don t know if anyone gets more awkward than Gabe but let s be honest this was more funny than cringey Tap to play GIF Tap to play GIF NBC Toby's utter disinterest and Gabe's lack of self-confidence make this short interaction immensely chuckle-worthy. View this video on YouTube youtube.com 14 Another Michael practical joke that went terribly wrong was him firing Pam NBC What started as a way to impress Ryan with a "Jamie Kennedy experiment" turned out to just be a really cruel and painstaking scene. View this video on YouTube youtube.com 15 Stanley s pretzel day fascination was wonderful NBC / NBCUniversal / Via Getty Images Stanley had some great running jokes about him being solemn – particularly his crosswords during meetings – but a rare bit of joyful emotion for pretzel day made for a super funny scene. View this video on YouTube youtube.com 16 But we can t talk about cringe-inducing moments without mentioning Michael kissing Oscar NBC This whole scene was intolerable. Definitely a NO moment from Michael... Of which there were many! View this video on YouTube youtube.com 17 Back to funny Michael moment – remember the burning of the foot NBC This whole scene is soooo good. From Michael's initial call of panic, to him explaining how he burnt his foot to the camera crew, it's absolute gold. Shout-out to Stanly's wry smile as he hears what Michael's done! View this video on YouTube youtube.com 18 In terms of uncomfortable episodes we need to talk about Phyllis and Bob s wedding NBC Talk about cringey! This whole episode was pretty tough viewing, not least due to Michael's attempts to walk Phyllis down the aisle in spite of her father's wishes. View this video on YouTube youtube.com 19 I simply had to include another one of Jim s pranks so here s my personal fave – the wrapped up desk NBC We got a few incredible *look-to-camera* moments from Jim here too. View this video on YouTube youtube.com 20 Bringing it back to cringe I give you the Diwali episode NBC Here Michael went FULL Michael – firstly with the proposal, and second with his attempt to kiss Pam. It's just... Wow. View this video on YouTube youtube.com 21 On the funnier side the CPR episode definitely needs a mention NBC This whole scene is absolutely priceless! The dancing to "Stayin' Alive" was brilliant, but Dwight's organ harvesting and Hannibal bit is what did it for me. View this video on YouTube youtube.com 22 It was painful when Michael broke up with Pam s mum on her birthday NBC From the moment Michael enquired about her age, and the "grandma" talk began, you just knew this scene was going to be difficult to stomach, and it most certainly was. The way he keeps on doing it with Pam and Jim there is so unbelievably awkward. View this video on YouTube youtube.com 23 Let s finish on a funny note – Dwight and Jim working TOGETHER NBC Their awful party planning skills made for a hilarious storyline, and it all worked out in the end with Kelly getting to have a nap at work! View this video on YouTube youtube.com Image credits: NBC unless otherwise stated. What moments do you find funniest or the most cringe-worthy from The Office Let us know in the comments below Share This ArticleFacebook PinterestTwitterMailLink TV and MoviesGet all the best moments in pop culture & entertainment delivered to your inbox.This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.