Ranking the 25 Best Characters on The Office

13. Toby Flenderson

Actor: Paul Lieberstein

Episodes: 141

Toby is the sad sack human resources rep. Technically, he is a corporate employee which leads to Michael viewing him as the enemy and he thinks Toby’s job is to “make everything lame.” Michael’s mission in life is making life miserable for Toby and in a fitting first appearance in “Diversity Day,” Michael kicks Toby out of a meeting, just because he can.

Toby endures Michael’s abuse throughout the show which results in Toby going out of his way to avoid Michael. But Michael tried to get rid of him for good by planting what he thought was marijuana in his desk, but it was only a Caprese salad.

Even though Michael hates him, Toby gets along well with his other co-workers. He and Jim used to sit by each other but Michael separated them for talking too much, but it’s a good thing because he’s obsessed with Pam.

In “The Negotiation” Darryl invites Toby to stay at his cousin’s house during a trip to corporate but denies Michael the same courtesy. Despite Michael’s hatred, Toby’s position as HR rep means that he occasionally has to advocate for Michael much to his reluctance.

Next: Phyllis Vance