The Office might be an ensemble series, filled with wacky and hilarious characters, but for the first seven seasons of its nine-season run, it was the regional manager of Dunder Mifflin Scranton, Michael Scott (Steve Carell), who was the centerpiece of the show. His co-workers might find Michael intolerable most of the time, but we love him. Yeah, he’s awkward on the most cringe-worthy of levels, a guy who tries too hard and often embarrasses himself and those around him, but it’s understandable.
Michael is a lonely man reaching out, wanting to be noticed, wanting to be loved, wanting to have friends. Despite this, there’s one man Michael Scott can’t stand, no matter what. Dunder Mifflin Scranton’s sad sack HR rep, Toby Flenderson (Paul Lieberstein), is Michael’s sworn enemy, even if poor Toby is just a guy wanting to be liked too. But how did this state of contempt towards Toby even start? When tracking Michael’s disdain for Toby, the actors reveal it all started with just one episode.
Why Does Michael Scott Hate Toby Flenderson?
It all comes down to one thing: Fun. Michael Scott just wants to have fun, but Toby Flenderson represents every corporate procedure that holds the Dunder Mifflin manager back from fun, freedom, and whatever else he wants to do in the workplace. Michael might have a mug that says “World’s Greatest Boss,” but most of the time work is the last thing on his mind, hence why he hates Toby. Dunder Mifflin is Michael’s stage. Every day he comes to work looking to do something fun or make someone laugh as part of his desperate need for attention. He’ll surprise you sometimes, showing just how much he’s capable of when he has to, such as when he leaves Dunder Mifflin to start The Michael Scott Paper Company. But for Michael, his co-workers are his family and social life. He doesn’t have much of anyone outside the office walls. These are the moments that mean everything to him.
Opposing that is the Human Resources representative, who is the antithesis of Michael and someone the Dunder Mifflin manager has no authority over, which means he cannot fire him, either. While Michael just wants to have fun, unwittingly harassing people and going too far in the process, it’s Toby’s job to rein him in. Toby, a dull, drab man with a voice that would put you to sleep, is the opposite of Michael’s energy. He’s not a mean man, and in almost every case he’s right to approach Michael and put a stop to his antics, but this determination to follow rules and be a killjoy makes Michael angry. He cares about almost everyone, but Michael has a special kind of hate for Toby Flenderson.
Michael Scott’s Worst Moments Involve Toby Flenderson
We laugh at how absurd he is, but Michael is truly awful to Toby. We see them clash from the beginning. In the show’s second episode, “Diversity Day,” Michael makes the flawed decision to hold his own sensitivity training. When Toby makes a joke about “sitting Indian style,” Michael kicks him out, saying, “That was offensive and lame. So double offensive.” It’s Michael who ends up being the offensive one, however. In Season 2’s “Casino Night,” Michael wants to have Boy Scouts at the company’s adult-themed game night. Toby rightfully shuts Michael down. It guts him with Michael responding, “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.”
During the Season 4 episode, “The Deposition,” Toby and Michael eat lunch together, with the former trying to help the latter. You wonder if this will be a breakthrough moment for the two. Nope! Instead, Michael responds by pushing Toby’s lunch on the floor as if he was a toddler. Michael couldn’t even let himself respect Toby. That would go against everything he believes in, which is that the HR rep sucks in every way imaginable. Pairing his actions with his words, Michael isn’t afraid to speak of his hatred for Toby either. In Season 6’s “The Chump,” while Toby is trying to give a lecture, Michael butts in. He can’t help but be the center of attention, and it especially riles him up that people would be forced to listen to Toby speak. “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,” Michael says.
In Season 4 of The Office, Michael gets one happy moment with Toby, and that is because the HR rep is leaving. In “Goodbye, Toby,” Michael throws an extravagant going away party, not in celebration of Toby’s accomplishments, but that he’s finally gone. It leads to perhaps Michael’s funniest moment, when Toby returns without Michael knowing about it. In “Frame Toby,” he runs into the man he was sure he’d never see again. Michael falls apart when their eyes meet, yelling, “No, God! No, God, please, No!” On The Office Ladies podcast, hosted by Pam’s Jenna Fischer and Angela’s Angela Kinsey, the three discussed this moment in great detail. In the script, Carell was just supposed to scream when he saw Toby. Carell knew Michael too well though. Michael’s hatred for Toby called for so much more.
Paul Lieberstein Reveals Why Michael Scott Hates Toby Flenderson
The man behind Toby Flenderson, Paul Lieberstein, wasn’t just an actor on The Office, but was one of the series’ writers, executive producers, directors, and a showrunner for four years as well. In a 2020 interview with the Today Show, he talked about the real-life origins of the Michael and Toby feud, which actually came from an annoyance Steve Carell felt for Lieberstein in one moment. During a Season 4 episode, Toby walks into Michael’s office to sign a birthday card with Lieberstein explaining, “I just came in his office during the middle of it, wrote on the card, and left, but it took a while to write, and Steve told me afterward he just felt, during that time that it took me to write, so much hate just swell up inside of him… That’s where it was born.”
That same year, Lieberstein explained to Ironclad just why Michael hates Toby so much. Though he shared the Season 4 birthday card story again, he added something new that most fans might find as a surprise: Michael and Toby were never meant to be enemies. “We never had this meeting where we were like, ‘Okay, what if Michael hates Toby?’ It just happened,” he said in the podcast.
It’s easy to see how that accident could have happened and led to comedy gold. The two characters are the clear opposite of each other, not just for what they believe in but for how they naturally act. Steve Carell and Michael Scott are energetic, their voices loud and bouncy, whereas Paul Lieberstein and Toby Flenderson are slower-paced in how they talk. One’s the tortoise, one’s the hare. They were destined to clash, and in doing so, they were destined to create some of modern comedy’s best moments. And to think it all started because of a slowly written birthday card.
