I once named everything I catch related to fictional characters in my White playthrough, from another series or from my OCs. It's not just random either, since I consider the Pokemon and the character I'm referencing. Some of my favourites are:
Springday the Musharna (Named after Suzumiya Haruhi, since 'haru' = spring, and Munna has flowers on its body. I was going to blatantly name Munna Haruhi, but mine was a guy, so I had to compromise. It turned out pretty nice for a name.)
Faraday the Zebstrika (It was Faraway at first, since zebra = horse = run long distances. However, I thought it didn't feel like a name after a while, so I slightly changed it. The character I was referencing before the change is May/Haruka from Pokemon, but it ended up being Kay Faraday from Ace Attorney Investigations. So, double reference!)
Simon the Excadrill (Ha ha, do I even need to explain just who the hell this guy is referencing? This name is simple and might be boring to some, but I sure do love me some TTGL references.)
Honorable mentions:
Adam the Samurott (Revolver Ocelot from M-M-M-Metal Gear, since I didn't want to be boring and just use Ocelot)
Lynne the Lilligant (Lynne from Ghost Trick, due to the gender and the flower on her head)
Hinawa/Mothman the Volcarona (Hinawa from MOTHER3, Mothman from Devil Survivor/SMT; the name depends whether Volcarona is a girl or a guy)
I think before I started seriously naming my Pokemon, I had some pretty stupid names, what with age and all. The worst of my nicknames has to be Fly the Starly. Thank god I lost my Pearl, but ugh...