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I like their attitudes... They're both quite similar, their type of humour makes me laugh.
Wasn't it spelt Tailz? Or am i thinking of the much cooler Knucklz (or however the flip you spell it)
Grrr this is bringing back memories now. That little bas**rd was never around when you wanted him and couldnt keep up. Didnt you also have to rescue him? God i hated Tails. I know i'm not the only one.
Duke Nukem
Samus Aran (or at least her suit)
Cole (GoW)
Barney (security guard in Half Life)
Mr Blonde
Don Weaso (CBFD)
Greg (CBFD)
The Great Mighty Poo (CBFD)
Brass Monkey (CBFD)
The Dung Beetles (CBFD)
Donkey Kong
Diddy Kong
There are actually some pretty cool player-created characters out there too: one of my old Linkshell Leaders in FFXI never once lost his cool but lost a bit of credibility because he was a 2ft tall Tarutaru.
My Night Elf feral druid was probably the coolest cat, ever, in World of Warcraft.