How Tux the Penguin Ruined It for Linux
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I'm still quite happy with Tux though, it's a sober mascot that's very simple/minimal, and is easily recognizable.
If you push me to name a bad logo -> Perl 6 Butterfly (IMHO that is what nightmares are made of, sorry)
I really like how Ubuntu turned this around and showed people that a usable linux is possible.