Our party is fighting a nuclear family of Royal Sea People, where the Dad (King) is basically a Fighter, the Mom (Queen) is a spellcaster, and the boy (Prince) is a rogue.
The Prince immediately rolls a nat 20 to hide from the party (supposedly to prepare a sneak attack) and by the time anyone rolls high enough to see him, he’s definitely out of the room.
Our Sorcerer uses Charm Person successfully on the King, who then, despite the Queen’s protests, sprints to the kitchen to get him Hot Dogs.
Bard (Ooc): Ok, since it’s just the Queen I’m gonna use Disguise Self to change into the son.
Sorcerer (Ooc): Oh….
Bard (Ooc): What?
Sorcerer (Ooc): Sorry I thought you meant you were going to disguise yourself as like the literal Sun.
Later the Son (Dave) did return and had eaten both of his parent’s hearts and transformed into an eldritch monstrosity; complete with eye-stalks, a side-ways shark mouth, and eight scuttling limbs. Our Bard had history with this kid and was more enraged than intimidated.
Bard (still disguised as the son’s human form): Hey Davey!
Bard (disguised): You should kill me first. I want you to see what you’re gonna look like after my friends kick your ass!
Potential Plays-of-the-Game included: The Ranger’s Wolf criting on a Bite attack, our Fighter stabbing this thing with a found trident and succeeding a strength contest with it, and our Sorcerer’s Wild Magic randomly turing everyone invisible (including the Monster itself).
After our party collectively knocking nearly 300hp off this boss, he was just about down for the count.
Bard: HEY, DAVEY! *Picks up the crown off the King’s head*
Bard: *Puts on Crown* *Casts Vicious Mockery* KING ME.
He lands the final blow. The monster is obliterated. Everyone is screaming. Including the DM. A great time is had.