Tag: The Office

“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 15^th 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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“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 15^th anniversary of its premiere this week (March 24, 2005). 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.”

We’ll start with the greatest sports moments in the show’s nine seasons. There are 24 of them in all that include a wide variety of different sports and one plotline that surrounds being a sports marketing agent (it DEFINITELY counts). Let’s count them all down:

24. Jim and Darryl join a sports agency (all of Season 9)

It’s the storyline that puts a strain on Jim and Pam’s marriage — hence why we ranked it last! — but that ultimately leads to them to move out of Scranton and to Austin, Texas. — Charles Curtis

23. Ryan Howard appears on a show that had character named Ryan Howard (“Promos” — Season 9, Episode 18)

When The Office premiered in 2005, Howard was in the middle of a season in which he would go from Triple-A Scranton/Wilkes-Barre and finish with the Philadelphia Phillies, winning NL Rookie of the Year. The other Ryan Howard — played by B.J. Novak — was starting out quite a character arc as a temp at Dunder Mifflin’s Scranton branch. Nearly eight years later, the Phillie met with Jim and Darryl at their sports agency to pitch them an off-the-wall sci-fi script. — CC

22. Darryl, Kevin and Jim are the Big 3 (“Spooked” — Season 8, Episode 5)

Darryl is LeBron James, Kevin is Dwyane Wade and Jim — reluctantly, because he hates dressing up for Halloween — is Chris Bosh. It’s some pretty minimal effort here because they’re just wearing jerseys, but hey, they got Jim to wear a costume. — Michelle Martinelli

I am Chris Bosh pic.twitter.com/EDRzrblV

— Jim Halpert (@JimboHalpert) August 17, 2012

21. Hey, it’s Julius Erving! (“Lice” — Season 9, Episode 10)

Jim meets with Dr. J and shoots with the legend who would be a potential investor in his Philadelphia agency. It’s fun to see Jim geek out over meeting his basketball idol. — CC

20. Rollerskating (“Ultimatum” — Season 7, Episode 13)

Dwight, Darryl and Andy go on an adventure in an attempt to meet women, and they end up at an indoor rollerskating rink in the middle of the afternoon. Naturally, they practically have the place to themselves, so Andy requests Dave Matthews Band, but “no hits, deep tracks only,” which translated to Ants Marching. — MM

19. Darryl’s disastrous KD impression (“Suit Warehouse” — Season 9, Episode 11)

This is too good. Darryl’s interview with Jim’s new sports marketing company goes so well, and he’s clearly feeling good about it. But his confidence got the best of him because he pretends to be Kevin Durant and takes and misses a shot. The ball hits the rim, then a light, and both the light and ball tumble into the fish tank below, killing the fish inside. — MM

18. Jim’s lacrosse snowball FAIL (“Classy Christmas” — Season 7, Episodes 11/12)

It’s somehow satisfying to see Dwight win a prank war with Jim for once, and it includes Jim taking a lacrosse stick — turns out he played? — loading it up with an icy ball and missing Dwight with a shot, breaking a window instead. Turns out he played… badly. — CC

17. Dwight finally earns his black belt (“Livin’ The Dream” — Season 9, Episode 21)

If you know anything about Dwight, you know him finally getting his black belt — after 20 years and $150,000 spent on training — is a huge deal. And he gets it from his new instructor, Sensei Billy (Michael Imperioli). — MM

16. Creed wins Casino Night … and Kevin loses (“Casino Night” — Season 2, Episode 22)

We’ll go back-to-back with two separate moments from a classic ep (yes, poker and casino games are sports!). Creed steals a bunch of chips and ends up with the prize for the most winnings on the night: a refrigerator from Vance Refrigeration, his first fridge ever (!). Meanwhile, Kevin — a World Series of Poker bracelet winner — somehow loses a hand to Phyllis. — CC

15. Dwight thinks Jim has a “tell” (“Casino Night” — Season 2, Episode 22)

It’s a mini-prank — Jim deliberately coughs to make Dwight think he has a huge hand in poker and Dwight keeps folding when he does it. Ha! — CC

14. Deangelo’s dunking fail (“The Inner Circle” — Season 7, Episode 23)

Will Ferrell’s four-episode appearance was good, but this has to be the best way any character on the show exits. — MM

13. Joe Montana (“Dinner Party” — Season 4, Episode 9)

This is not even close to one of the weirdest, awkward moments from this episode, but Andy finds the most obscure way to describe Joe Montana while playing a guessing Charades-type game. Joe Camel and the state where Helena is the capital? Come on, Andy. — MM

12. Pam volleyball (“Company Picnic” — Season 5, Episode  28)

“Maybe I played a little in junior high. And in high school. Maybe a little in college. And went to volleyball camp most summers!”

Pam being significantly better than everyone else at volleyball leads to the other team, the corporate office, forcing her to go to the hospital when she barely rolls her ankle to get her off the court. And that leads to the heartwarming moment when she and Jim find out they’re expecting.

11. Jim’s soccer fail (“Dream Team” — Season 5, Episode 22)

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How many different ways can Jim fail to impress his new boss? After lying about liking and playing soccer to Charles Miner, he finds another one. Excellent guest star Idris Elba kicks the ball to Jim, who ducks, and Phyllis gets drilled in the face instead. — MM

10. Michael attempts to leave Dunder Mifflin with no-look hoops shot (“Goodbye, Michael” — Season 7, Episode 22)

“Catch you on the flippity flip!” (misses) “Flippity flip!” — CC

9. Michael checks Toby into the boards (“Michael’s Birthday” — Season 2, Episode 19)

Michael Scott forever. Besides quoting Wayne, he lays the body and cellys like a true boss. 😂 pic.twitter.com/dI8l18pIY5

— Bring Hockey Back (@BringHockeyBack) November 2, 2016

A good reminder that Steve Carrell played hockey growing up and that Toby is the worst. Also, it’s a legal check, Scott doesn’t leave his feet. — CC

8. Michael and Dwight at the dojo (“The Fight” — Season 2, Episode 6)

All I hear whenever I think of this is Kevin’s “Sweep the leg!” — CC

7. Jim and Darryl play ping-pong (“The Deposition” — Season 4, Episode 8)

Jim is good, Darryl is better, but Kelly’s smack talk wins it all. — MM

6. The Office Olympics gold medal for Jim (“The Job” — Season 3, Episode 23)

We’re breaking this one out separately from the Office Olympics ep because Jim discovering the yogurt-lid medal Pam put in his folder as he’s interviewing for a Jan Levinson’s old Dunder Mifflin job in New York leads to the beginning of them dating. “Alright, then … it’s a date.” — CC

5. Agent Michael Scarn saves the NHL All-Star Game (“Threat Level Midnight” — Season 7, Episode 17)

I love this whole episode because Michael Scott is the only person who would spend years shooting and reshooting a movie about saving the NHL All-Star Game with a James Bond-esque villain and a subplot almost entirely lifted from The Karate Kid. Also, Dwigt. — MM

4. The whole 5K episode (“Fun Run” — Season 4, Episode 1)

There are so many great moments in this whole episode centered around The Michael Scott Dunder Mifflin Scranton Meredith Palmer Memorial Celebrity Rabies Awareness Pro-Am Fun Run Race: Andy’s Band-Aids on his nipples, Michael carbo-loading with an obscene amount of fettuccini alfredo and Andy attempting to draft off Kevin. However, the best thing about this race is Kelly putting the finish line three miles away from the office instead of mapping a circle. — MM

3. The Wayne Gretzky, er, Michael Scott quote (“Michael Scott Paper Company” — Season 5, Episode 23)

Rick Hahn on Ohtani: “We know this is a long shot, as I said. We do have a responsibility to leave no stone unturned, exploring every possible avenue to be in the best position going long term. You miss 100% of the shots you don’t take said Wayne Gretzky and Michael Scott.” pic.twitter.com/0Gbh2VUJxO

— Sox On 35th (@SoxOn35th) December 2, 2017

Maybe one of the most perfect images from the show ever that can be used in so many ways. — CC

2. The Office Olympics (“Office Olympics” — Season 2, Episode 3)

This is one of the best episodes in general because we see so many characters’ personalities come alive. There’s Oscar and Kevin’s paper football game (a.k.a. “Hateball”), Pam’s creativity with the decorations and yogurt-lid medals, Phyllis winning in the national sport of Icelandic paper companies and the race around the office with filled coffee mugs. And, of course, Jim’s enthusiasm for it all, a trait Pam so clearly loves:

“The thing about Jim is when he’s excited about something, like the office Olympics, he gets really into it, and he does a really great job. But the problem with Jim is that he works here, so that hardly ever happens.”

And the national anthem at the end with the doves really is an incredible moment. — MM

1. The entire Dunder Mifflin basketball game (“Basketball” — Season 1, Episode 5)

It’s all perfect — Michael calling fouls, his long free-throw routine, Jim competing with his rival, Roy, over Pam’s affection, Dwight getting buckets and Michael not, and so much more — CC

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