Nice list.

I'll have a go at fisking it.
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Originally Posted by Morthoron
1) Gandalf sparred verbally with Wormtongue; hippies had words with Tricky Dick.
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Wormtongue was a fifth-columnist. Gandalf sided against him.
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2) Gandalf smoked pipeweed; hippies had weed-pipes.
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But it would only be conjecture to say that Gandalf's pipeweed had any hallucinogenic qualities.
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3) Gandalf hung around with Dwarves and Hobbits; hippies hung out with Eric Burdon of the Animals, who described himself as 'an over-fed, long-haired leaping gnome'.
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But would Gandalf have spilled the wine or taken the pearl?
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4) Gandalf was long-haired, bearded and disheveled; hippies were like that too, only younger.
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Only in the gray days. When he went to Gandalf the White, he was quite well cleaned up.
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5) Gandalf once knew every spell in all the tongues of Elves or Men or Orcs; hippies were...ummm...forgetful too.
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No argument there!
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6) Gandalf took hikes; hippies hitchhiked.
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Hiking has more character than bumming rides. As does riding Shadowfax (the Rolls Royce of horses).
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7) Gandalf burned pinecones; hippies burned draft cards.
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Gandalf used those pinecones as weapons. Perhaps molotov cocktails would be a better comparison?
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8) Gandalf helped end the War of the Ring; hippies helped end the Vietnam war.
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But Gandalf ended the War of the Ring by fighting
in it and winning.
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9) Gandalf was considered a troublemaker and disturber of the peace; hippies? ditto.
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I would venture that his disturbing and troublemaking had a slightly more noble purpose than, say, Woodstock.
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10) Gandalf was called Stormcrow by Theoden; Stormcrow? Man, like, what an awesome name for a band!
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Seek and ye shall find:
http://www.youtube.com/watch?v=k7_VoGPPNXo
I'm not sure if this actually qualifies as hippie music, though. Hippies did make some decent music. I'm really not fond of this group.
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Oh and I vote for ++Samwise
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Good choice, although I think we're behind in this round.
By the way, positive rep inbound to you for coming up with this list.