Of those I can actually remember, I'd say the stupidest was Turnip the Oshawott. At least it matched the color of his head!
FuzzyWuzzy the Joltik. Hey, at least it's somewhat descriptive...
Ah man, I used to be terrible at coming up with nicknames for Pokemon, especially when I was a lot younger. Two gems that come to mind right now are "Flype" the tailow (which I think was a combination fly and flap) and "Horntle" the lapras (which was a combination of horn (referring to the spike things on its shell) and turtle). -_-
After seeing the Day-Care Couple demotivational poster, I named my Marill "son". It was hilarious actually seeing the Day-Care Couple demand money in exchange of my "son"... lol?
We're 2 cool 4 u
I named my Zebstrika "Ryde" because it was a horse. However, that nickname backfired when I realized it was female.
There are no stupid nicknames, only unfitting ones.
A long time ago on my FireRed, I chose Charmander and and nicknamed him 'Dino'.
Only forgetting to type the 'o' in after pressing OK.
I'll be the very best. Like no one ever was.
I just put a Ditto on the GTS in hopes I get a foreigner Ditto.
Its nickname? "Masuda pls"
Me verás volar por la ciudad de la furia...
What happens in Ferris Wheel... stays in Ferris Wheel.
I believe I gave a Virizion the nickname 'Qantas' because its head kind of looked like a Boeing 747.
I named a Jigglypuff ''Dicks'', in Blue.
This was before I knew english, and had common sense.