Most fans know Toby for playing comedic characters on other web shows, but they got an unexpected surprise when Toby appeared on the Black Box TV episode "This Is For You Baby!" as a vengeful boyfriend whose girlfriend is cheating on him with his best friend. Yikes! They state in the commentary that they picked Toby for the role precisely because people were used to him being comical.
Toby appears in the Stranger Things episode "Sacred Cow" as Father Micheal Hutchsons, a serious priest and a Reasonable Authority Figure who has come to investigate a fellow priest and his adopted Ditzy Genius son over a video of prayers turning into energy caught on tape, but it turns out Father Micheal is an ex-communicated priest and a Serial Killer who is part of a cult that worships Sufficiently Advanced Aliens that have been feeding off of the energy of human prayers.
This will likely be averted with Toby's cameo appearance in the upcoming slasher flick Smiley, as he revealed in one of his Vlogs that he will play the role of a Class Clown/Jerkass in said film.
In an episode of One of those Faces, Stranger Things, Toby plays the role of a Guardian Angel sort of figure. It's a far more serious role then what most fans would expect from him.