Most of the inappropriate and cringe humor in The Office is pretty tongue-in-cheek, and the viewers are supposed to understand that the jokes and behavior aren't being condoned but mocked.
But even with that caveat, there are a lot of moments from the series that aren't as easy to watch as they once were.
1. Michael's Hitler impression
This happens in literally the first episode when Michael is showing off for Ryan. Why he thinks an accurate Hitler impression is something to brag about or do in front of a complete stranger (or anyone, really), we'll never know.
2. Michael's "Asian character"
Thankfully we only see Ping, Michael's "Asian character" twice — first in the Season 2 premiere "The Dundies" and later in "Goodbye, Michael" — but even once would be more than enough.
3. Michael's "Asian girlfriend"
In the Season 3 episode, "Benihana Christmas," Michael, Andy, Jim, and Dwight head to Benihana (or as Michael puts it, "Asian Hooters"), where Andy proceeds to talk Michael up to the waitress (and hopes she might have a friend for him).
They then bring back two completely different waitresses to the office, where Michael forgets which one he's on a "date" with. He ends up marking her arm with a Sharpie to keep track of her (something Jim laughs about when Michael tells him about it later).
Kat Ahn, who played Andy's "date," has actually since revealed her discomfort with the episode and that she felt she was "just there to be a joke."
The racism issue aside, it's probably fair to say both these women were way too young for Michael and Andy — when Michael extends one of the waitresses an invite to Sandals, she says she "has school."
4. Andy's underage girlfriend
Andy apparently has a thing for younger women, because later in Season 3, during "Product Recall," we find out Andy has been unwittingly dating a high schooler. Jim is present for the revelation, and while he's clearly not supportive, he could be more uncomfortable with the fact that Andy is in his thirties dating someone that young (even if he thought she was technically not a minor).
5. Michael Klump
Ping isn't Michael's only offensive character. In "Weight Loss," he breaks out "Michael Klump," a fat character he brings to life with the partially-inflated Sumo suit from the Season 3 episode, "Beach Games."
6. Most of "Diversity Day"
The second-ever episode of the series is...rough. After Michael is chastised for his Chris Rock impression, he puts together his own diversity presentation, which involves having people pretend to be other races (which, as far as he's concerned, includes "Jewish" and "Jamaican"), and concludes with him doing a horrific imitation of an Indian person to Kelly, who has no idea what's been going on.
7. Belsnickel's sidekick
In the Season 9 episode "Dwight Christmas," Dwight gets to throw a Christmas party for the office, dressing as Belsnickel, a figure from German folklore who, as Jim puts it, is basically Santa but dirty and worse.
When Oscar alerts the staff that Belsnickle has a sidekick called "Black Peter" who's essentially an enslaved person brought to life via Blackface, the reaction is understandably not great.
In the original run of the show, we at one point see Dwight's assistant, Nate, dressed as Black Peter, complete with the Blackface, but the moment has been removed from the episode on Peacock (though we do glimpse the aftermath at one point).
8. Michael fake-firing Pam
Unlike pretty much everything else on this list, this moment from the pilot isn't rooted in political correctness, but rather just treating someone like garbage for no reason. It's also the first time (of many) that we see Michael doing something completely ridiculous without considering the possibility of a negative reaction, even though no rational person would find being fake-fired funny.
9. Dwight tricking Holly into thinking Kevin is "special"
In the Season 4 finale, "Goodbye Toby," Dwight "hazes" Holly by convincing her Kevin is intellectually disabled. The joke carries on into the next season when she learns the truth and is told "that is very offensive" by Angela.
10. Pretty much anything to come out of Todd Packer's mouth
Honestly, the character might not even exist, and if he did, we'd probably only see him twice: when he made his first horrific joke, and when he got fired. He makes just 15 appearances throughout the entire series, but manages to get jokes in about Jim's sexuality (the first time we see him he asks Jim if he's "still queer" and later says Karen must be a man or "Halpert got scared straight."
He also shows up to the office Christmas party with mistletoe hanging over his groin
11. Michael "flashing" the office
In the Season 3 episode, "Women's Appreciation," when Michael finds out Phyllis has been flashed, he first asks if the flasher didn't see Pam or Karen (from behind). He then proceeds to pretend to flash everyone, poking his finger through the zipper of his pants. He also later tells Toby to "show us [his] penis."
12. "Gay Witch Hunt"
The Season 3 premiere, "Gay Witch Hunt," is really just one big mess, and if the branch hadn't potentially been on the chopping block (and it wasn't a TV show), I really think this would have been what actually got Michael fired. He essentially sexually assaults Oscar by forcing a kiss on him, nearly getting the company sued. (He still ends up costing them money, as Oscar gets a three-month paid vacation and a company car.)
Plus, the whole catalyst for the issue is Michael calling Oscar a homophobic slur before finding out he's actually gay. He then later uses the r-word to describe why he'd never have called Oscar that if he'd known he was gay.
13. Hiding from the Indian-American IT guy
In the Season 2 episode, "Email Surveillance," Michael spots an Indian man in a turban pull into the Dunder Mifflin parking lot and walk toward the building. He immediately assumes the guy is a terrorist and tells everyone to hide, before discovering he's merely the new IT guy, Sadiq.
14. Michael talking about how "sexy" Stanley's daughter is
In the Season 2 episode, "Sexual Harassment," Michael, thinking Stanley just has a photo of a "centerfold in the Catholic school girl's outfit" hanging up at his desk, says it's "hot" and "sexy" and that he loves staring at it before Stanley informs him it's a photo of his teen daughter who goes to Catholic school.
15. Michael showing off a nude photo of Jan without her consent
When Michael first reveals that he went to Jamaica with Jan in the Season 3 episode, "Back From Vacation," it's done accidentally. His attempt to email a photo of himself with Jan, who's topless, to Todd Packer, though, is very intentional, and results in everyone in the warehouse (plus all the people they forward it to) seeing it.
Still, judging from Jan's reaction to the photo in Season 4, she didn't know it existed, so she surely wouldn't have wanted it passed around by dozens of her subordinates.