Suggestions by @connieblackwood

Papineau (Look Outside)

as Monk in Fictional Characters by D&D Class

Sophie (Look Outside)

as Rogue in Fictional Characters by D&D Class

Hellen (Look Outside)

as Ranger in Fictional Characters by D&D Class

Joel (Look Outside)

as Fighter in Fictional Characters by D&D Class

Leigh the Grinning Beast (Look Outside)

as Barbarian in Fictional Characters by D&D Class

Sybil (Look Outside)

as Cleric in Fictional Characters by D&D Class

The Visitor (Look Outside)

as Sorcerer in Fictional Characters by D&D Class

Sam (Look Outside)

as Warlock in Fictional Characters by D&D Class

Hellen (Look Outside)

as Knife (Generic) in Characters by Weapon of Choice

Sophie (Look Outside)

as Slingshot in Characters by Weapon of Choice

Papineau (Look Outside)

as XI. Justice in Sort by Tarot

Sybil (Look Outside)

as 0. The Fool in Sort by Tarot

The Visitor (Look Outside)

as XIII. Death in Sort by Tarot

Sam (Look Outside)

as XVI. The Tower in Sort by Tarot

Sam (Look Outside)

as Crest of Friendship in Sorting characters into Digimon Adventure crests

Roaches (Look Outside)

as “Wait we had homework?” in Can I Copy Your Homework

The Shadow (Look Outside)

as “I’ll help you with it!” in Can I Copy Your Homework

Monty (Look Outside)

as “Wait we had homework?” in Can I Copy Your Homework

Xaria (Look Outside)

as “Lol Nope” in Can I Copy Your Homework

Dan (Look Outside)

as “Bold of you to assume I did the homework” in Can I Copy Your Homework