The top 10 worst moments of ‘The Office’s’ Michael Scott (and then some)

By Alex Ewald,
"Great Scott!" A look back at Steve Carell's Michael Scott, the boss we loved to hate.

There are too many cringe-worthy moments to count with Michael Scott, played masterfully for seven seasons by Golden Globe-winner Steve Carell.

But narrowing seven years’ worth of awkward down to a significant 10 or so helps understand that complexity so characteristic to the U.S. version of The Office.

The long-running comedy (finally) is nearing the home stretch and winding down a number of strange plotlines — Jim and Pam fighting over a dumb new job? Erin and Pete being pedastaled as the new PB&J? Andy turning into a total jerk? So, a retrospect of why Steve Carell’s iconic bossman made awkward both painful and hilarious to watch is desperately needed.

Last week’s episode of NBC’s The Office introduced a potential new boss for Pam Halpert (Jenna Fischer), who’s contemplating a move with Jim (John Krasinski) from Scranton to Philadelphia. She interviewed for a new job with the manager (Bob Odenkirk) whose resemblance to Steve Carell’s former Dunder Mifflin regional manager was a little too close for comfort.

10. When he wrecked the entire Scranton warehouse:
(from “Boys and Girls,” season 2)

Michael proves the extreme fodder for Daryl Philbin (Craig Robinson), Scranton’s competent warehouse foreman who has to clean up after Michael’s mess. He just had to play with the forklift…

9. When he spanked his intern-nephew:
(from “Nepotism,” season 7)

American Horror Story’s Evan Peters really can’t catch a break, even if he was a horrible intern. To top it off, Michael ended up in mandatory counseling sessions with his arch nemesis, dreary HR rep Toby Flenderson.

“Are we good?” No, Michael, that is the opposite of what is good.

8. Whenever he ‘fake-fired’ people:

It was in very poor and very awkward taste when Michael would have to tell his employees he wasn’t firing them.

An innocent Pam started cried while the new temp Ryan (BJ Novak) was still in the room (from the pilot):

Stanley, on the other hand, got pretty mad (from “Did I Stutter?” season 4):

7. When he drove into a lake:
(from “Dunder Mifflin Infinity,” season 4)

Also arguably the moment I consider when The Office starting jumping that shark, Michael misunderstands the car’s GPS directions to bear right and promptly turns into a lake. He treats it as a turning point in hating useless technology while Dunder Mifflin launches its new website.

6. When he kissed Oscar:
(from “Gay Witch Hunt,” season 3)

The horrifying kiss with the straight-man gay accountant (Oscar Nuñez) was unscripted, so the reactions of the cast members are actually just that. Unscripted — and horrified.

5. When he made a big deal about cooking his foot:
(from “The Injury,” season 2)

It was an honest mistake for Carell to have submitted this episode for his Emmy nomination. Through the entire episode, Michael was just too much of an inconsiderate man-child for viewers or voters to have any sympathy.

Like having Dwight fan his foot:

Bringing in a guy who uses a wheelchair to educate the Scranton branch on “living with disabilities”:

And failing to notice or care about Dwight’s concussion on their way to the hospital:

4. When he changed the Christmas gift exchange:
(from “Christmas Party,” season 2)

After paying a ton of money for Ryan’s gift, a video iPod (remember when those were expensive? LOL), Michael got offended when Phyllis gave him a pair of hand-knit oven mitts. So, he wanted something better and decided to change the game to a White Elephant exchange, in which everyone goes around and can either pick from the pile or steal someone else’s gift. Logically.

“YANKEEEEEE SWAP!”

Then things like this happened:

Along with Phyllis crying, a furious Angela throwing lightbulbs at a wall and stomping on them, and Toby getting Stanley’s nameplate bought for Kelly.

(Dwight also ended up taking Jim’s gift for Pam, a teapot filled with items on inside jokes along with a note whose contents Jenna Fischer won’t reveal, according to DVD commentary.)

3. Pretty much all of “Diversity Day" (season 1):

After a lame presentation on diversity awareness from “Mr. Brown” (no, Michael, his name was actually Mr. Brown), Michael revels in his ignorance by setting up a different kind of Diversity Day. He has all the office workers put cards with races/nationalities on their foreheads. He puts the “Martin Luther King, Jr.” card on his head, obviously.

Especially this:

2. When he broke up Stanley’s marriage:
(from “Gossip,” season 6)

In an effort to get in on the gossip loop and be a part of the conversation, Michael spreads a rumor about Stanley having an affair that turns out to be true. So, naturally, he starts false rumors about everyone else in the office that quickly spread — Pam is pregnant (true), Angela is dating an 81-year-old billionaire who owns a Quizno’s, Kelly is anorexic, and Kevin has another person inside his body controlling him. And Stanley’s wife still finds out.

1. “Scott’s Tots" (season 6). There are no words:

Ten years earlier, Michael promised a class of third-graders, "Scott's Tots," that he would pay their college tuition. Yeah, he really did promise that. And in season six, Michael had to tell these now-seniors hoping for a free ride that he couldn’t follow through. Who could? It’s really one of the most painful episodes having to watch Michael clumsily stumble around that promise.

Pam’s #realtalk: “This is a terrible, terrible thing you’ve done.” Finding the comedy is challenging until this:

Lithium batteries over college tuition, obviously.

Michael is just the perfect case of childish arrested development — he never knows better a lot of the time. And that’s ultimately understandable once his more sympathetic traits were revealed as the character arc progressed, like his desperation to be liked and desire to have a family, his innate business sense as a salesman, and his well-intentioned heart.

Some noteworthy moments:

When Michael celebrates an office birthday the wrong way (“The Alliance,” season 1):

When he sleeps with Pam’s mom (“The Lover,” season 6):

And won’t stop dating her when Pam finds out:

“Let’s get some raw meat on that face," and he doesn't even say "TWSS":

When he willingly dates a married woman (“The Chump," season 6); the rest of the office gives him crap for it.

When he can’t remember what his Benihana’s waitress date looks like, so he marks her arm (from “A Benihana Christmas,” season 3).

When he gets mad that Phyllis gets to be Santa for the Christmas party, so he suits up as St. Nick and then as Jesus.

And when he picks Stanley for his basketball team, "of course" (“Basketball,” season 1):

Really any time he’s around Stanley 'the Manly':

But “Dinner Party” (season 4) deserves its own category of cringingly awkward TV moments, thanks to Michael and Jan:
From Jan's (Melora Hardin) sleeping arrangement, Michael's emasculated plasma TV and beer sign, to his…ahem, medical issues. I could write a whole story about its sheer dimensional brilliance. The episode, all one big train wreck and a thoughtful character study, is pretty much one of the best stories of TV comedy — and of all time. All Time!

I’m pretty sure Jan wanted to have a three-way with Jim (not Pam—she hated Pam)

When ish hits the…plasma TV?:

And “that’s what she said!”

Photo Courtesy of Byron Cohen/NBC.

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