Thomas Wolfe and Asheville hold similar, problematic positions within the concepts and realities of Appalachia. Wolfe was born in the heart of Southern Appalachia but lived a life that was anything but rural. As a child, he traveled out-of-state routinely with his mother, and when he finally learned of Look Homeward, Angel’s publication, he was in Vienna. Wolfe sought adventure, exploration, and fame, in many cases the opposite of a stereotypical Appalachian existence. Asheville itself exists as a politically blue island in a sea of red. Its traffic, businesses, and pace differ sharply from towns and communities just minutes away. The beautiful mountain vistas seen from the west side of downtown can be viewed alongside the homeless, below the balconies of multi-million dollar apartment complexes. Paradoxes abound. Being from Asheville, Wolfe was objectively Appalachian, but his work is usually placed somewhere outside of the Appalachian canon. For much of his writing, that is just, but for other works like the unfinished novel The Hills Beyond, the play Welcome to Our City, and stories like “Child by Tiger,” the Appalachian-ness becomes blurred. I will seek to establish an idea of literary Appalachian-ness and argue for Wolfe’s position inside and outside of it using critical works about the region. In examining Wolfe and his place within Appalachia, we can establish a framework for evaluation of other authors, books, cities, and further ask the question of if we should still ask the question.