Michael Scott (Steve Carell) and Toby Flenderson (Paul Lieberstein) have one of the most hostile relationships in TV history. They dislike each other, but it's more one-sided than it sounds. Michael's antics are an HR nightmare — literally— for any company, but Toby takes it all in stride.
Still, their interactions make for some awkward moments, and in most cases, they are the highlight of every episode of The Office. To commemorate their dysfunctional relationship, we've ranked the best moments between Michael and Toby.
10 You Are The Silent Killer
From: "The Surplus" (Season 5, Episode 10)
When Michael Scott discovers a surplus at the end of the quarter, he consults the office on what to spend the money on. Pam wants new chairs while Oscar wants a new copier. Toby, however, wants to get the office tested for radon and asbestos. "These are the silent killers," Toby tells Michael with concern in his voice. "You are the silent killer," Michael replies, "go back to the annex."
Michael is clearly fed up with his HR rep in this scene. He wants to do something a little more fun with the money, and while testing for dangerous gasses is important, it's not as flashy as some chairs, or a jacket from Burlington Coat Factory.
9 I Forgot To Give You A Donut
From: "Michael's Birthday" (Season 2, Episode 9)
It's Michael's birthday, but Kevin has a cancer scare. Still, Dunder Mifflin Scranton's regional manager won't let that bring the office down. In fact, he brings donuts to the office for everyone to enjoy, but when Toby forgets it's Michael's big day, things go sour fast. Toby goes to grab a baked treat, but Michael tells him he forgot to let him have one, referencing the forgotten birthday moments earlier. Toby, shocked, thinks Michael is joking, but that couldn't be farther from the truth.
This scene is incredibly awkward and isn't mentioned nearly enough compared to other Office quotes. Still, it perfectly encapsulates the passive-aggressive relationship Michael has with Toby.
8 The Most Expensive Scene Of Threat Level Midnight
From: "Threat Level Midnight" (Season 7, Episode 17)
Michael spent years working on his spy epic Threat Level Midnight, and finally, he was ready to show his employees — all of whom actually performed in the film. One scene, however, stood out above the rest: when the film's antagonist, Goldface, shoots and kills an innocent hostage. That hostage is played by Toby, so Michael made sure that the character dies in the most over-the-top manner imaginable, and the moment was shot from as many angles as possible. In a talking head directly after, the regional manager admits that it was the most expensive scene in the movie for that reason alone.
While we can just let that statement stand for what it is, it's hilarious to think that Michael's hatred for his HR rep is so deeply rooted, he wrote his death into a movie.
7 Double Offensive
From: "Diversity Day" (Season 1, Episode 2)
For diversity day in the office, Michael decides to hold a sensitivity training seminar in an attempt to rid the office of ignorant views (most of which are held by him). Yet, as Toby walks into the conference room, where Michael's lesson is held, he says "Hey, we're not all going to sit in a circle Indian style are we?" If anyone else said this, Michael would probably find it hilarious, but since it was Toby, Michael kicks him out. When Toby apologizes, the regional manager of the Scranton branch says, "No, this is not a joke. OK? That was offensive and lame. So double offensive."
It's just hostile enough that everyone in the room feels uncomfortable, but since it was Toby, it was sort of expected.
6 I'd Shoot Toby Twice
From: "The Chump" (Season 6, Episode 25)
When Toby is lecturing the office on his radon test kits, Michael constantly interrupts the presentation with fart noises. So, the HR representative asks for a little bit of respect while he's talking, but Michael refuses, telling him the office will die of boredom before they die of radon.
When that gets a laugh, he takes it a step further by saying, "Right? And if I had a gun, with two bullets, and I was in a room with Hitler, Bin Laden, and Toby, I would shoot Toby twice." That doesn't fly as well as the regional manager would have hoped, but Dwight saves the day by showing how you could, in theory, kill all three with one bullet instead.
5 Goodbye Toby
From: "Goodbye, Toby" (Episode Season 4, Episode 18/19)
Michael's dislike for Toby is unmatched. It's so bad, in fact, that he spent thousands of dollars he saved in his shoe to throw a party when he learned his HR rep was leaving the office to try and start over in Costa Rica. His disdain for Toby is only multiplied in this episode as Michael starts developing feelings for Toby's replacement, Holly Flax. This makes Toby's departure a little more magical for Mr. Scott.
Still, the going away party was always going to be a big event, and it lived up to the anticipation. There were fireworks, a Ferris wheel, and, most importantly, a parody of Supertramp's classic"Goodbye Stranger" performed by Michael called "Goodbye Toby." You could tell this was something Michael dreamed about for years as he sang with glee. His performance was pretty awful, but he gets bonus points for enthusiasm.
4 Getting Lunch
From: "The Deposition" (Season 4, Episode 12)
When Jan Levinson (Melora Hardin) decided to sue Dunder Mifflin for her termination, Michael Scott was caught in the middle. On one side, there was his girlfriend and the prospect of a multi-million dollar settlement, but on the other, there was the company he'd been loyal to for years — the company that gave him the job he loves, a nice parking spot, and employees he adores.
Despite their animosity, Toby saw the difficult situation Michael was in and told him so over lunch. He even compared the situation to his parent's divorce when he was a child. Unfortunately, Michael wasn't very receptive to the sympathy sent his way, and reacted by pushing Toby's lunch tray onto the floor.
3 Of All The Idiots
From: "Goodbye, Toby" (Season 4, Episode 18/19)
When the time comes for Toby's exit interview, Michael doesn't hold back. He invites the soon-to-be former Human Resources representative into the conference room, but decides to start the proceedings before Holly — the new HR-person —can oversee the ordeal. So, the two sit down, and Michael gets very real, telling Toby, "Can I just say that, of all the idiots, in all the idiot villages, in all the idiot worlds, you stand alone, my friend."
He then gives Toby a "present" that is just a rock with a note that reads "suck on this" attached.
2 Why Are You The Way That You Are?
From: "Casino Night" (Season 2, Episode 22)
Michael has organized an office casino night in the warehouse to help raise morale and give back to charity. The event was catered by hooters, had a bar, and featured actual casino games to boot. To cap off the night, Michael wanted a group of Boy Scouts to accept a novelty-sized check from whoever had the largest chip-count.
Unfortunately, due to the reasons above, Toby shot the idea. Frustrated, Michael looked his HR representative dead in the eye and said, "Why are you the way that you are? Honestly, every time I try to do something fun or exciting, you make it not that way. I hate so much about the things that you choose to be."
This is actually one of our favorite quotes from the series, and it's delivered with such conviction from Carrell that you actually believe, for a split second, there is real anger there.
From: "Frame Toby" (Season 5, Episode 9)
Michael is unaware that Toby returned to the office a week ago and believes Jim is joking when he says the man Michael hates more than anyone is actually back. So, he goes to Toby's old desk to investigate. When he gets to the annex, however, Toby isn't there. Michael is visibly relieved when he sees this and even calls out to Jim for what he thought was a prank. That's when Toby's voice echos through the room with a simple "Hi" and Michael loses all control, screaming "No" at the top of his lungs for the remainder of the cold open.