Once again, please forgive the double post, but I thought this up this morning (in the shower, of all places!) and wanted to add it.
My fav Mr. Herriman moment was in "Beat with a Schtick" (hey, another one!) when he and Bloo are discussing Bloo's "gentleman's challenge." I loved it when he told Bloo, "Well, let's just say you have an hour and fifteen minutes left. * Evil laugh *" (Or something to that effect. All I remember is the evil laugh!)
I loved this moment because it's such a contrast from Mr. Herriman's straight-laced attitude. It was almost like Bendy possesed him for a sec...
But this is my fav.