Generally speaking, Toby is not a funny character on The Office. He's meant to be a punching bag for all of Michael's jokes and comes across very diminutive and lacking in personality. That's all on purpose, of course, but it also didn't lead to many scenes where he was in the spotlight. It was always at his expense.
Still, there are plenty of underrated moments where Toby is hilarious. Moments that don't get a lot of attention. This list is dedicated to all those moments when everyone's least favorite HR rep should actually be one of the favorites.
Does anyone have a camera!?
Everyone knew that Toby had a crush on Pam. Even if the show only actively reminded viewers about once per season. But it was always there, and it comes to the forefront during Toby's going away party. Pam gifts Toby a picture of everyone in the office and he remarks that she isn't in it. Of course, she was taking the picture. Toby then its that he doesn't have any pictures with Pam, because why would he, but realizes he doesn't have a camera.
In a fit of desperation, he turns to the office and cries out far too loudly, "Does anyone have a camera?"
HR is a joke
All of his life at Dunder Mifflin, Toby has pretty much tried to do the right thing. He's always stopping conversations before they get too far into the inappropriate and while it doesn't always have the effect he desires, his intentions are certainly always there.
This time, however, Toby doesn't even bother. When a conversation goes the way of... rectal things and their effect on Andy's impotence, Erin asks Toby to step in. To which Toby can only say, "Erin, HR is a joke. I can’t do anything about anything."
Humphrey Bogart impression
Toby just doesn't have a lot of personality, so when it shines through, it can often get overlooked. And while what became of Toby's personality and character choices in the final season is highly questionable, there is a fun side plot in Toby's fascination of the Scranton Strangler.
When he finally resolves to go see the Strangler, he speaks to the camera outside the prison, expecting a friendship to start up. He's so giddy that he does a cringe-worthy Humphrey Bogart impression that can't be missed.
Already Gone
It's easy to lose track of the number of times that Michael kicks Toby out of meetings. Sometimes he just insults him, sometimes he yells at him, but his objective is always to do his job without Toby's interference.
In this particular instance, Michael is talking about Fundamentals and underlines 'mentals' saying you'd have to be mental not to enjoy it. Toby wisely says, "the 'fun' is in it." Michael looks at the board as the office acknowledges Toby's remark and before Michael can even turn around to kick Toby out, he's already half-way out the door.
Great American Mysteries
Toby's Chad Flenderman novels didn't come out of nowhere. His affection for mystery stories was established in season six, in a moment that is really easy to miss. In "The Banker," when Dwight pretends to be Toby to ensure that Sabre does, in fact, purchase Dunder Mifflin, Dwight's entire ploy is dependent on one thing—he left a copy of Great American Mysteries in Toby's favorite stall.
It doesn't work. But Toby does bring the book back with him when he returns. So... it did work. Kind of.
Tony
When Nellie first arrives at the office, distinctly uninvited, Toby introduces himself—accidentally—as "Tony." Pam asks what he said and Toby gets so gloriously awkward talking about how he accidentally said the wrong name. It's just wonderful.
It's such a small moment, but it's hilarious, both because it happened, and because Pam draws attention to it, and then Jim. Then Toby has to try to defend himself, which magnifies the awkwardness tenfold. Did Toby really flub his own name or was he so bored with himself and attracted to Nellie that he thought he'd try out a new persona?
Write Your Own Damn Novel
Toby is desperate for friends. For someone to talk to, to associate with, just so that he isn't always so alone. But no one cares about his book about, as Angela put it, "a sex-crazed black detective."
Jo Bennet, however, stumbles upon Toby's Chad Flenderman novels when Sabre goes through the computers of every employee in an attempt to find the mole. She offers criticism to Toby and one would think that Toby would be thrilled to talk to someone about Flenderman. That's not the case, though.
"Write your own damn novel," he says.
Beach Day
As one of the best episodes in the history of The Office, Beach Day has so many focal points. None of which involve Toby, because Toby was left back at the office. According to Michael, someone had to stay back. Of course, it was going to be Toby because Michael wanted this to be the most magical day, and that automatically means no HR intervention.
There are only a few cutbacks to Toby, but each time, he's still dressed in his awful beach gear, wide-brimmed hat and all, going about work as if nothing has changed.
No More S'Mores
Given how quietly and without excitement Toby talks, it takes some very specific choices to make him funny, because there's not a lot of flexibility here. But the specific choices made in this particular instance were perfect.
When Toby goes on Ryan's wilderness retreat instead of Michael (who wasn't invited), Toby recounts the story to a handful of folks in the office. He talks about how they had so many s'mores that eventually, he had to say, "no more s'mores, no more s'mores."
Bacchus' Friend
Robert California's one season in charge brought out the best in a lot of minor characters such as Gabe Lewis and Toby Flenderson. At Robert's pool party, he gives a tour to some of the men of the office, and Oscar and Toby hit off a surprise (and fragile) friendship based entirely on Toby's choice of wine. Oscar compliments the choice, but Toby has no idea what he's chosen.
This comedic side plot hits a crescendo when Toby os pouring wine into Oscar's mouth. Oscar spits it out, laughing, and cries, "I am Bacchus, god of wine!" Toby's hesitant response: "And I am Bacchus's friend!"