I started pondering silly items to maybe include in the game I run on Fridays. So far, I have a sword and shield in mind for the rogue.
The Rapier of Sharp Wit
Rapier. 1d8 piercing damage. Magic weapon, 7 charges. Expend a charge to roll to hit vs. target's Charisma statistic instead of Armor Class. Regains 1d4 charges per day.
The Buckler of Blame Deflection
Shield. +1 Armor. Gain advantage on all deception checks when defending against accusations.
Both would require attunement, and both could be incredibly overpowered, but funny as heck. I can already tell this campaign will go off the rails anyway. Why not nudge it further along? Please chime in if you have better name suggestions or a background story for these items! It'll be a few sessions before they appear for the player in question.