This chapter discusses Chris Ware’s graphic novel Jimmy Corrigan: The Smartest Kid on Earth (2000) in the context of its internal repetition of particular tropes and images, which ultimately produce a moment of textual decision for the reader as to whether they believe the story has ended happily or unhappily. It also discusses Jimmy Corrigan in the context of Ware’s characteristic style and his larger career arc, as well as in the context of the late 1990s/early 2000s transition in graphic narrative from a relatively niche publishing concern aimed at teenagers and the counterculture towards a global literary-artistic movement aimed at highly educated middle-class professionals that no longer needs to “justify” serious consideration. Ware emerges with Jimmy Corrigan as perhaps the key figure in this moment of transition, and remains one of the most acclaimed artists working in the medium today, even as he has moved into yet more formally experimental work like Building Stories (2012).