“Sometimes, I’ll start a sentence and I don’t even know where it’s going. I just hope I find it along the way.”
Well said, Michael Scott. That’s the perfect way to introduce For The Win’s tribute to The Office, the NBC comedy that celebrates the 15th anniversary of its premiere this week (March 24). For the show that’s still so embedded in American and internet culture, we’ll break down everything from the best sports moments to the best couples. Because, as Wayne Gretzky Michael Scott says, “You miss 100 percent of the shots you don’t take.”
For all its laughs or heartwarming moments, The Office is built on cringeworthy moments. Those impossibly awkward exchanges or silences can make the show painful to watch — sometimes simply because of the situation and other times because several episodes haven’t aged particularly well.
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So we’re here to address one aspect from The Office that remains regularly debated on the internet: Which episode is the cringiest? Here’s our ranking of the top 10.
10. “Crime Aid” — Season 5, Episode 5
This is not close to the worst thing Michael pretends to have — more on that later — but it’s awkward nonetheless when he fakes having Bruce Springsteen tickets to auction off. He drags it on and on only to then lie about them being stolen. — Michelle Martinelli
9. “Company Picnic” — Season 5, Episode 28
Michael accidentally letting it slip during a skit that the Buffalo branch of Dunder Mifflin would be closing down — IN FRONT OF THE BUFFALO EMPLOYEES — due to the recession is just the worst. THE. WORST. Just thinking about it makes my stomach do flips. — Charles Curtis
8. Every single episode with Robert California — Season 8
Robert California’s first appearance in the Season 7 finale was weird but fine in that small dose. And then he came back the next season, and every scene he’s in is just uncomfortable. James Spader’s performance is obviously next-level to elicit such feelings, but oh my god is it cringey. — MM
7. “Double Date” — Season 6, Episode 9
Michael dating Pam’s mother Helene was awkward enough. But then he finds out her age and BREAKS UP WITH HER IN THE MIDDLE OF HER BIRTHDAY. GAHHHHH!!! — CC
6. “Andy’s Ancestry” — Season 9, Episode 3
When Andy believes he’s distantly related to Michelle Obama, he’s beaming with pride about it, but everyone in the office then presumes that means his ancestors enslaved people. And when he asks his mom about it, he then makes the distinction that they transported enslaved people, which is better in absolutely zero ways. — MM
5. “Phyllis’ Wedding” — Season 3, Episode 15
I wanted to dig myself into a hole and live in it during Michael’s speech, but at least he was redeemed when he “found” Uncle Al after Bob Vance kicked Michael out. — CC
4. “Gay Witch Hunt” — Season 3, Episode 1
Michael is such an insensitive idiot throughout the show, but one of the worst consequences of his actions is when he outs Oscar. He uses a homophobic slur and is too dense and ignorant to appreciate why it’s offensive, and after he’s reprimanded for being so obtuse, he outs Oscar. And then he finds new ways to make it worse, culminating in him kissing Oscar in front of everyone in the conference room — a moment which Steve Carell improvised. It’s so painful. — MM
3. “Diversity Day” — Season 1, Episode 2
Yeesh. All sorts of awkward and problematic, top to bottom, right up until the moment Kelly (Mindy Kaling) slaps Michael for his extremely racist impersonation. It was cringeworthy then and 10 times more so now, and it’s a reminder that early Michael Scott was more of a jerk than a lovable buffoon. — CC
2. “Dinner Party” — Season 4, Episode 9
Oh, believe us. It wasn’t easy choosing between this and the next ep on this list to be No. 1.
But one of the wonderful things about The Office is they figured out a way to make some cringeworthy moments and episodes HILARIOUS while also making us watch through our palms over our faces.
And that’s “Dinner Party.” Jan dancing to the song from her former assistant, Hunter, that’s clearly about “that one night” they spent together. The “snip-snap-snip-snap!” quote about getting (and un-getting) a vasectomy. The fact that Pam is starving and there’s no food to be seen. The teeny flatscreen!
It makes you want to crawl into a ball. But you’ll be shaking with laughter while in a ball. And that’s why it’s No. 2 — CC
1. “Scott’s Tots” — Season 6, Episode 12
“I’ve made some empty promises in my life, but, hands down, that was the most generous.”
After seeing this episode for the first time, I refused to rewatch it until recently, when I had to for this ranking to remind myself why I refuse to rewatch it. It was absolutely just as cringey, awkward and torturous to get through as I remember. Every time Michael delays breaking the promise he made to a bunch of kids — he told third graders if they graduated from high school, he’d pay for college, assuming he’d be a millionaire by then — the episode dives down to a new level of uncomfortable. He has so many opportunities to deliver the bad news to the now-high school seniors — who are wearing “Scott’s Tots” t-shirts and perform a song and dance celebrating him — but he keeps his brutal charade going. And when he finally, finally owns up to it, his consolation prize for them is a computer… battery.
I don’t know if it’s Michael crushing kids’ dreams, the agonizing anticipation building throughout the episode or the realism of the crushing price of college — or some combination of all of the above — but there is no doubt that this episode is The Office‘s cringiest. And I’m never watching these 22 minutes again. — MM
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