In his own eyes, The Office's Michael Scott is known by his employees for being the world's best boss, his witty song parodies and his brilliant "that's what she said" jokes. To the outside world, Dunder Mifflin's longtime regional manager will be remembered most for his complete lack of self-awareness and cringe-worthy moments that have made his seven seasons on the NBC comedy so painful — and painfully funny — to watch. With just two episodes left of Steve Carell's tenure, we look back at one of his character's most enduring legacies, Michael's most cringe-inducing moments.
Lesson learned: Michael takes corporate's diversity seminar into his own hands when he finds the entire seminar is happening because of him. To help further the lesson along — or so he says — he designates an ethnicity to each of his employees, who then must walk around with that label taped to their forehead so they'll experience life as a minority. Unfortunately, a then-very timid Kelly Kapoor didn't get the memo and when Michael begins to talking to her about working in a convenience store with an overly dramatized Indian accent, he gets a big slap across the face. ("Diversity Day," Season 1)
The ship is sinking!: What do you get when you put a bunch of disgruntled employees on a boat and add alcohol, dancing and some motivational speaking? A leadership training exercise only Michael could have dreamed up. Despite his best laid plan, Michael quickly gets into a power struggle with "Captain Jack" (a hilarious Rob Riggle) when he tries to shout his corporate presentation over the captain's speech. To move his presentation along, Michael falsely tells the passengers that the boat is sinking and although his employees know better, many others immediately jump off the boat and Michael ends the cruise handcuffed to a pole outside. (Oh, and did we mention his dance moves?) ("Booze Cruise," Season 2)
The kiss: After the Season 2 finale gave fans the highly anticipated first kiss between Jim and Pam, Season 3 kicked off with another memorable lip lock. When Michael discovers that Oscar is gay (a clue hinted to viewers many times throughout Season 2), he accidentally outs Oscar to rest of the branch. Michael tries his best to make it right with a well-meaning but horribly offensive "homosexuality seminar." Oscar soon threatens to quit, Michael attempts to reconcile the situation again, but with a smooch instead of another speech. "At least we put this matter to bed. That's what she said. ... or he said," Michael says. ("Gay Witch Hunt," Season 3)
Dinner party from hell: When Michael and Jan invite Jim, Pam, Andy and Angela over for a dinner party, nobody was informed that awkward couple blowout was on the menu. Despite their public persona of a happy, loving couple, a short tour through their condo only reveals how dysfunctional Jan and Michael's relationship really is (he sleeps on the floor, she is obsessed with her growing candle business and she's put him through three — count 'em, three — vasectomies. As Jim says, "Michael and Jan seem to be playing their own separate game. And it's called 'Let's See How Uncomfortable We Can Make Our Guests.'" The night ends with Jan breaking Michael's two most treasured possessions: his plasma TV and his Dundie Award. ("The Dinner Party," Season 4)
You're fired: Michael is reunited with his long-lost love, Holly, at the Dunder Mifflin company picnic, but their reunion quickly turns bittersweet when they accidentally tell the Buffalo branch they are closing in the middle of a (supposedly funny) skit. ("Company Picnic," Season 5)
Date Mike: Pam should know better than to fix Michael up with one of friends, but she's pleasantly surprised when the two hit it off right away and her friend — gasp — actually finds Mike charming and funny. Unfortunately, charming Michael suddenly transforms into the obnoxious and sleazy Date Mike as soon Michael realizes the date is a setup. He plays air guitar on the pool, dons a backwards Kangol hat and busts out irresistible lines like this: "Hi, I'm Date Mike. Nice to meet me. How do you like your eggs in the morning?" ("Happy Hour," Season 6)
Good timing: One of Michael's most recent blunders is also one of his most heartfelt moments on the series. After he discovers his cold sore is actually herpes, Michael proceeds to call all of his ex-girlfriends to tell them to get tested, including love of his life Holly. They initially reminisce about their romantic past over the phone and at the end of the day, he leaves a message proclaiming his love for her... before letting her know she should talk to a doctor because she might have herpes. ("Sex Ed," Season 7)
The Office airs Thursdays at 9/8c on NBC.