A piccy of Gandalf, when he was known as Olorin, before he came to Middle Earth.
I’ve drawn Olorin before but it got deleted in the great December purge. I was never very happy with how it turned out, so I decided to have another go at it. Started by digging out my copy of the Silmarillion, which says:
Wisest of the Maiar was Olorin. Though he loved the Elves, he walked among them unseen, or in form as one of them, and they did not know whence came the fair visions or the promptings of wisdom that he put into their hearts.
It also says that he liked to hang out in the forests of Valinor, so I figured that I’d do that most unusual of things and actually put a background in. Then I sketched the figure out, and took some inspiration for the face from pictures of Ian McKellen when he was young.