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.
Portrayal in adaptations
2007: 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.
- As Radagast narrates terrified to Gandalf his encounter with the Necromancer in Dol Guldur, Gandalf offers him to pull from his pipe some "Old Toby" to calm down.