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The leaf took its name from the Hobbit who introduced pipe-weed to the Shire, the original "Old Toby", Tobold Hornblower, who grew the first true pipe-weed in his gardens in the days of Isengrim Took II about the year 1070 of Shire-reckoning.
How Old Toby came by the plant is not recorded, for to his dying day he would not tell.
The Lord of the Rings Online
In The Lord of the Rings Online, the smoke from Old Toby Pipe-weed takes the form of a large heart with a ring inside it.