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Freezo, I'm going to tell you what my great-uncle told me: put down the gun.
 
— Sir Grimsby, Camp Righteous

The archivist of the Waterdeep Historical Society who travels with the Dragon Friends during the Tomb of Annihilation. An awful imperialist dickhead, Sir Grimsby died when Freezo prayed to God/Dave for him to be killed and no one minded very much. His (initial) final words were "Well... fair enough.".

Sir Grimsby was later resurrected to fulfill his original purpose of moving the plot forward by providing key information about the history and anthropology of Chult (a much required thing). After fulfilling his task, Freezo - in succession - dropped him of an airship, blasted him with an Eldritch Spear and spat on him, with Hing declaring: "He's so dead, you can't bring him back ever Dave!".

Yet Grimsby would turn out to be truly not so dead. After leaving the Yuan-Ti temple in Tomb of the Nine Gods, Pt 1, the Dragon Friends find him alive and well in the nearby campsite, writing about his miraculous survival in his diary:

Dear chums—dear fellow Waterdavians. What a ripping yarn I have to tell you! Pip pip! So there I was, plunging to my death, after my friend the wizard had no doubt due to being overwritten by some dark magic been forced to drop me to the craggy rocks below. Thinking fast, I bl... I hadn’t thought about this... I... flung out my coat tails in the way that I’d seen a bat in the jungle do and glid glide to safety. The sea was choppy, and I wouldn’t have survived had I not landed on a passing whale that took me to shore! I killed it for ambergris. Spot of luck there, anyway. And here I am, finally – as far as I can tell, the only person in the lost city of Uuuumuuuuuu. How famous I’ll be, how wealthy I’ll be, how respected I’ll be!

Freezo immediately tries to kill him by turning himself into gas and having Grimsby choke on it, but the plan fails. The party eventually settles on using Grimsby as a crash test dummy in the Tomb of Annihilation, which he doesn't seem to mind - possibly due to brain damage. It becomes his downfall as he is persuaded to enter a silver chest, swap places with Freezo. After a button press, his frozen corpse is ejected and his head shatters into many pieces.

He's been dead so many times... eh, he'll be back.
 

Cocktail[]

See Sir Grimsby Lives! (Cocktail) for a cocktail named after the undying dickhead.

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