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1.
A creature evolved from the modern squid, that has developed a concrete social structure and has taken to swinging through the trees like a gibbon. In 200 million years, the Squibbon will inherit "civilization" from we petty vertibrates.

Featured on the BBC's "The Future Is Wild"
"The squibbons swung from branch to branch, their boneless tentacles allowing complete flexibility in mobility"
by Matthew February 11, 2004