The Most Cringe-Worthy Moments in ‘The Office’

If you’re a fan of The Office, you can probably think of several instances when the show made you cringe. The awkward moments on the show not only made the series memorable, but more to audiences — even today. These are some of the most cringe-worthy moments from The Office.

Rainn Wilson, John Krasinski, Kate Flannery, Hansford Rowe, Steve Carell, Phyllis Smith, and Angela Kinsey
Rainn Wilson, John Krasinski, Kate Flannery, Hansford Rowe, Steve Carell, Phyllis Smith, and Angela Kinsey | Paul Drinkwater/NBCU Photo Bank/NBCUniversal via Getty Images

Cringe comedy is what makes ‘The Office’ so funny

In Brian Baumgartner’s latest venture, An Oral History of The Officethe cast and crew of the series dissect what made the show such a success. 

As it turns out, it was all about the pacing. The interesting rhythms and unique comedic timing made The Office a cringe-worthy comedy. 

“The rhythms were not like any kind of comedic rhythm you would ever see,” co-executive producer Teri Weinberg explained. “We took pride in the super long pauses.” 

The super long pauses Weinberg referred to made for some of the most cringe-worthy moments on the show. Ironically, fans and the cast alike enjoy those moments the most. 

Michael Scott was the king of cringe 

Most of The Office‘s most cringe-worthy moments are thanks to Michael Scott. 

There was the time he replaced his girlfriend’s ex-husband’s face in a family photo.

Later, when the Stamford branch shut down and Scranton absorbed it, Michael made all of the employees climb onto the conference room table — regardless of their size or physical ability.

And don’t forget when Michael discussed Jan’s (Melora Hardin) “assets” during her deposition against the company. 

Or when he aired footage from the fictional Fundle Bundle, where a young Michael said: “I wanna be married and have 100 kids so I can have 100 friends, and no one can say no to being my friend.”

Thanks to Michael Scott, fans of The Office have a hard time choosing their favorite cringe-worthy moment. 

‘Scott’s Tots’ is the most cringe-worthy moment on ‘The Office’ 

“The season 6 classic, ‘Scott’s Tots,’ famously took cringe to the extreme,” Baumgartner said during his podcast. 

Fans will remember the episode where Michael found himself unable to pay for the college tuition of a group of high school students. Despite his promise, Michael had to relay the bad news after being celebrated at a special ceremony.

“Many fans have told me that this episode, for them, is the most difficult to watch,” Baumgartner added. “There are even subreddits dedicated to this very topic.” 

Michael Scott wasn’t always the cause of the cringe-worthy moments on ‘The Office’ 

While it’s true that most of the cringe-worthy moments on The Office stemmed from something Michael did, some of the best cringe-worthy moments had nothing to do with the “World’s Best Boss.” 

Other notable moments included the time Andy Bernard (Ed Helms) got rejected by Julia (Erica Tazel) — a client of Stanley’s (Leslie David Baker) — in the parking lot after he attempted to kiss her.

“Speaking of cringe…” one fan wrote on Reddit. “Never forget the Nard Dog Guarantee rejected kiss.” 

There’s also the time Jan held her baby shower at the office after the baby was born.

Plus — Phyllis’ (Phyllis Smith) wedding.

And don’t forget about Toby’s (Paul Lieberstein) awkward flirting with Pam (Jenna Fischer). 

Or the time Kevin (Baumgartner) dropped his world famous chili all over the office floor.


How ‘The Office’ Accidentally Became One of the Funniest Shows on Television

See? It’s not just about Michael Scott. 

Are these moments uncomfortable to watch? Absolutely. But they’re what made watching The Office so enjoyable.